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Molbank
Volume 2024
Issue 2
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Molbank, Volume 2024, Issue 2 (June 2024) – 43 articles

Cover Story (view full-size image): The compound 3,5-di-(pyridin-4-yl)-1,2,4-thiadiazole (L1) is known to react with metal ions to form coordination polymers and polygons. In this work, we decided to explore the reactivity of L1 with 1,4-diiodotetrafluorobenzene (1,4-DITFB) to evaluate the possibility of preparing supramolecular structures using σ-hole interactions between halogen-rich compounds and pyridine tectons. Notably, 1,4-DITFB owns two iodine atoms disposed in the phenyl ring, which are activated by the presence of four fluorine substituents. We report here on the synthesis and characterization of the novel halogen-bonded co-crystal of 3,5-di-(pyridin-4-yl)-1,2,4-thiadiazole and 1,4-diiodotetrafluorobenzene. View this paper
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7 pages, 503 KiB  
Communication
N-Methoxycarbonyl-9,12-Dimethoxy-Norchelerythrine: A Novel Antifungal Type-III Benzo[c]phenanthridine from Zanthoxylum simulans Hance Seedlings
by Diego Cárdenas-Laverde, Diego Quiroga and Ericsson Coy-Barrera
Molbank 2024, 2024(2), M1839; https://doi.org/10.3390/M1839 - 21 Jun 2024
Viewed by 670
Abstract
Zanthoxylum simulans Hance, commonly known as Sichuan pepper, is a well-known medicinal plant recognized for its potential as a source of bioactive specialized metabolites. As part of our interest in natural antifungal compounds, the present study describes the discovery of an unreported N [...] Read more.
Zanthoxylum simulans Hance, commonly known as Sichuan pepper, is a well-known medicinal plant recognized for its potential as a source of bioactive specialized metabolites. As part of our interest in natural antifungal compounds, the present study describes the discovery of an unreported N-alcoxycarbonylbenzo[c]phenanthridinium salt, N-methoxycarbonyl-9,12-dimethoxy-norchelerythrine 1 (a type-III benzo[c]phenanthridine), isolated from Z. simulans seedlings, which were propagated under controlled greenhouse conditions. Six-month seedlings were harvested and subjected to cold acid–base extraction. Chromatographic techniques achieved the isolation of 1 from raw alkaloid extract. The structural elucidation of 1 was accomplished through comprehensive spectroscopic analysis, including nuclear magnetic resonance and high-resolution mass spectrometry. Fusarium oxysporum, a fungal pathogen responsible for substantial agricultural losses, was exposed to different concentrations of the novel compound, exhibiting potent antifungal efficacy (IC50 < 3 µM) and fungicide effects. These findings highlight the potential of benzophenanthridines as antifungal leads and underscore the importance of exploring natural products for agricultural applications. Full article
(This article belongs to the Section Natural Product Chemistry)
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5 pages, 377 KiB  
Short Note
2-{(E)-{{(R)-1-[(1R,5S,6R)-3,3-Dimethyl-2,4,7-trioxabicyclo[3.3.0]octan-6-yl]ethyl}imino}methyl}-6-{[(diphenylphosphino)oxy] phenyl}palladium(II) chloride
by Stéphane Guillarme and Christine Saluzzo
Molbank 2024, 2024(2), M1838; https://doi.org/10.3390/M1838 - 20 Jun 2024
Viewed by 623
Abstract
An unsymmetrical PCN palladium pincer complex 2-{(E)-{{(R)-1-[(1R,5S,6R)-3,3-dimethyl-2,4,7-trioxabicyclo[3.3.0]octan-6-yl]ethyl}imino}methyl}-6-{[(diphenylphosphino)oxy] phenyl}palladium(II) chloride based on an iminophosphinite ligand bearing two fused five-membered cycles, one of which containing a THF ring, was prepared in an eight-reaction sequence from [...] Read more.
An unsymmetrical PCN palladium pincer complex 2-{(E)-{{(R)-1-[(1R,5S,6R)-3,3-dimethyl-2,4,7-trioxabicyclo[3.3.0]octan-6-yl]ethyl}imino}methyl}-6-{[(diphenylphosphino)oxy] phenyl}palladium(II) chloride based on an iminophosphinite ligand bearing two fused five-membered cycles, one of which containing a THF ring, was prepared in an eight-reaction sequence from a sustainable and enantiopure starting material, isosorbide, in a 20% overall yield. Full article
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8 pages, 1498 KiB  
Communication
Synthesis of 2-[(3,4,5-Triphenyl)phenyl]acetic Acid and Derivatives
by Monika Mazik and Pierre Seidel
Molbank 2024, 2024(2), M1837; https://doi.org/10.3390/M1837 - 20 Jun 2024
Cited by 1 | Viewed by 1057
Abstract
New phenylacetic acid derivatives with potentially valuable biological activities and the ability to act as starting materials for various functionalizations have been prepared by a multi-step synthesis. Starting from 2,6-dibromo-4-methylaniline, the synthetic route involves the construction of the basic aromatic structure (3,4,5-triphenyltoluene) (two [...] Read more.
New phenylacetic acid derivatives with potentially valuable biological activities and the ability to act as starting materials for various functionalizations have been prepared by a multi-step synthesis. Starting from 2,6-dibromo-4-methylaniline, the synthetic route involves the construction of the basic aromatic structure (3,4,5-triphenyltoluene) (two steps), followed by its conversion into 2-[(3,4,5-triphenyl)phenyl]acetic acid and derivatives (up to five steps). Based on this multi-step synthesis, five compounds not previously reported in the literature were synthesized; the literature-known 3,4,5-triphenyltoluene was synthesized for the first time in the manner described. This synthesis is applicable for the preparation of numerous new representatives of this class of compounds. Full article
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6 pages, 1312 KiB  
Short Note
5,10,15,20-Tetrakis-(4-(3-carbamoyl-pyridyl)-methylphenyl)porphyrin Bromide
by Giuseppe Satta, Silvia Gaspa, Luisa Pisano, Lidia De Luca and Massimo Carraro
Molbank 2024, 2024(2), M1836; https://doi.org/10.3390/M1836 - 13 Jun 2024
Viewed by 656
Abstract
The synthesis of a new tetracationic porphyrin derivative is described. Contrary to the best known derivatives in the literature, which are derived from 5,10,15,20-tetrakis-4-pyridylporphyrin (TPyP), in this procedure we start from 5,10,15,20-tetrakis-(4-carboxymethoxyphenyl)porphyrin (TPPCOOMe), obtained by the condensation reaction between pyrrole and 4-formylbenzoate. The [...] Read more.
The synthesis of a new tetracationic porphyrin derivative is described. Contrary to the best known derivatives in the literature, which are derived from 5,10,15,20-tetrakis-4-pyridylporphyrin (TPyP), in this procedure we start from 5,10,15,20-tetrakis-(4-carboxymethoxyphenyl)porphyrin (TPPCOOMe), obtained by the condensation reaction between pyrrole and 4-formylbenzoate. The reaction is carried out in refluxed xylene, avoiding the use of halogenated solvents. The final product, 5,10,15,20-tetrakis-(4-(3-carbamoyl-pyridyl)-methylphenyl)porphyrin bromide (P15p), exhibits four cationic portions that make it soluble in water and suitable for G4 stabilization. The choice to synthesize a derivative of TPPCOOMe is based on the idea of having a possible stabilizer that, unlike those obtained from TPyP, shows the cationic moieties farther from the porphyrin core and thus closer to the phosphate groups present on the G4 loops. Full article
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5 pages, 1166 KiB  
Short Note
(S)-1-Methyl-2-oxoimidazolidine-4-carboxylic Acid
by Ashley L. Dey, Majid Motevalli, Isaac Abrahams and Peter B. Wyatt
Molbank 2024, 2024(2), M1835; https://doi.org/10.3390/M1835 - 12 Jun 2024
Viewed by 823
Abstract
(S)-1-Methyl-2-oxoimidazolidine-4-carboxylic acid 1 is an analog of (S)-pyroglutamic acid, a key component of naturally occurring peptide hormones and synthetic pharmaceutical candidates. The reaction of (S)-2-amino-3-(methylamino)propionic acid with COCl2 and aqueous NaHCO3 followed by ion exchange [...] Read more.
(S)-1-Methyl-2-oxoimidazolidine-4-carboxylic acid 1 is an analog of (S)-pyroglutamic acid, a key component of naturally occurring peptide hormones and synthetic pharmaceutical candidates. The reaction of (S)-2-amino-3-(methylamino)propionic acid with COCl2 and aqueous NaHCO3 followed by ion exchange afforded 1, which was recrystallized from acetonitrile and then characterized by IR, 1H NMR, 13C NMR, polarimetry, elemental microanalysis, high-resolution mass spectrometry and single-crystal X-ray diffraction. The acid 1 crystallized in the orthorhombic chiral space group P212121 with cell constants a = 6.2275(4) Å, b = 8.3963(5) Å, c = 24.9490(14) Å. The X-ray crystal structure revealed that two distinct conformers of 1 occur at alternating positions within helices which are supported by hydrogen bonds. Each molecule of 1 is linked to its two neighbors in the helix by a total of three hydrogen bonds, and four molecules of 1 are contained within each turn of the helix. The pattern of hydrogen bonds illustrates a preference for the carboxylic acid group to act as a hydrogen bond donor and for the urea unit to be a hydrogen bond acceptor. Full article
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6 pages, 816 KiB  
Short Note
[(N-benzamidomethyl)(N-benzoyl)amino]methyltriphenylphosphonium Tetrafluoroborate
by Jakub Adamek, Wiktoria Kaczmarczyk and Dawid Sapia
Molbank 2024, 2024(2), M1834; https://doi.org/10.3390/M1834 - 7 Jun 2024
Viewed by 608
Abstract
In this study, [(N-benzamidomethyl)(N-benzoyl)amino]methyltriphenylphosphonium tetrafluoroborate was synthesized at 80 °C, starting from N-benzoylaminomethyltriphenylphosphonium tetrafluoroborate, by a specific α-amidoalkylation reaction using Hünig’s base as a catalyst. N-benzoylaminomethyltriphenylphosphonium tetrafluoroborate acts as both an amidoalkylating agent and a nucleophile precursor. [...] Read more.
In this study, [(N-benzamidomethyl)(N-benzoyl)amino]methyltriphenylphosphonium tetrafluoroborate was synthesized at 80 °C, starting from N-benzoylaminomethyltriphenylphosphonium tetrafluoroborate, by a specific α-amidoalkylation reaction using Hünig’s base as a catalyst. N-benzoylaminomethyltriphenylphosphonium tetrafluoroborate acts as both an amidoalkylating agent and a nucleophile precursor. The structure of the compound obtained was confirmed by spectroscopic methods (1H-, 13C-, 31P-NMR, IR) and HR-MS analysis. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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5 pages, 550 KiB  
Communication
A New Method for the Synthesis of 1-(1-Isocyanoethyl)adamantane
by Dmitry Pitushkin and Gennady Butov
Molbank 2024, 2024(2), M1833; https://doi.org/10.3390/M1833 - 6 Jun 2024
Viewed by 721
Abstract
A novel single-step method has been developed for the synthesis of 1-(1-isocyanoethyl)adamantane from 1-(1-adamantylethyl)amine, chloroform, and t-BuOK, in a dichloromethane/tert-butanol (1:1) medium, yielding 92%, which is 27% higher compared to the known method, without the use of highly toxic compounds. [...] Read more.
A novel single-step method has been developed for the synthesis of 1-(1-isocyanoethyl)adamantane from 1-(1-adamantylethyl)amine, chloroform, and t-BuOK, in a dichloromethane/tert-butanol (1:1) medium, yielding 92%, which is 27% higher compared to the known method, without the use of highly toxic compounds. The product was characterized using 1H and 13C NMR spectroscopy, GC-MS, and elemental analysis. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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7 pages, 2154 KiB  
Short Note
Dichloro-μ2,μ2-naphthalene-1,8-diyl-bis(N,N,N′,N′-tetramethylethylenediamino)tetracopper(I)
by Matthew J. Ray, Maria Laura Saviantoni, Alexandra M. Z. Slawin, David B. Cordes and Petr Kilian
Molbank 2024, 2024(2), M1832; https://doi.org/10.3390/M1832 - 5 Jun 2024
Viewed by 840
Abstract
A highly reactive dicuprate/CuCl aggregate, Nap(Cu4Cl2)(TMEDA)2 (2, Nap = naphthalene-1,8-diyl, TMEDA = tetramethylethylenediamine), was synthesized by the reaction of 1,8-dilithionaphthalene(TMEDA)2 with four equivalents of CuCl. The X-ray crystal structure of this complex shows that the [...] Read more.
A highly reactive dicuprate/CuCl aggregate, Nap(Cu4Cl2)(TMEDA)2 (2, Nap = naphthalene-1,8-diyl, TMEDA = tetramethylethylenediamine), was synthesized by the reaction of 1,8-dilithionaphthalene(TMEDA)2 with four equivalents of CuCl. The X-ray crystal structure of this complex shows that the four copper atoms form a bent parallelogram-shaped core, with terminally bonded chlorine atoms. The naphthalene ring is bonded through carbons in the 1 and 8 positions (peri-positions), each bridging two copper atoms. Full article
(This article belongs to the Section Structure Determination)
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8 pages, 1244 KiB  
Communication
Introducing Bis(5-(Trifluoromethyl)pyridin-2-yl)amine Chelating Unit via Pd-Catalyzed Amination
by Nikolay A. Korinskiy, Anton S. Abel, Violetta A. Ionova, Stanislav I. Bezzubov, Alexei D. Averin and Irina P. Beletskaya
Molbank 2024, 2024(2), M1831; https://doi.org/10.3390/M1831 - 4 Jun 2024
Viewed by 994
Abstract
We report a one-step synthesis of trifluoromethyl-substituted di(pyridin-2-yl)amine-based ligands. N-(hetero)aryl-substituted bis(5-(trifluoromethyl)pyridin-2-yl)amines were obtained from 2-bromo-5-(trifluoromethyl)pyridine and corresponding aromatic amines via Pd-catalyzed amination reaction in the presence of a Pd(dba)2/BINAP catalytic system. Four new ligands were prepared in good to high [...] Read more.
We report a one-step synthesis of trifluoromethyl-substituted di(pyridin-2-yl)amine-based ligands. N-(hetero)aryl-substituted bis(5-(trifluoromethyl)pyridin-2-yl)amines were obtained from 2-bromo-5-(trifluoromethyl)pyridine and corresponding aromatic amines via Pd-catalyzed amination reaction in the presence of a Pd(dba)2/BINAP catalytic system. Four new ligands were prepared in good to high yields and characterized by NMR, IR spectroscopies and mass spectrometry. The structure of one of the products was additionally supported by X-ray analysis. Full article
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8 pages, 1072 KiB  
Short Note
(±)-R,S-2-Chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide
by Diyana Dimitrova, Stanimir Manolov, Dimitar Bojilov, Iliyan Ivanov and Paraskev Nedialkov
Molbank 2024, 2024(2), M1830; https://doi.org/10.3390/M1830 - 3 Jun 2024
Viewed by 1066
Abstract
In this study, we report the synthesis of (±)-2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide through the reaction of 7-amino-4-methyl-2H-chromen-2-one with (±)-2-chloro-2-phenylacetyl chloride. The in vitro anti-inflammatory activity of the new compound was evaluated, and the results indicated that it exhibited superior activity [...] Read more.
In this study, we report the synthesis of (±)-2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)-2-phenylacetamide through the reaction of 7-amino-4-methyl-2H-chromen-2-one with (±)-2-chloro-2-phenylacetyl chloride. The in vitro anti-inflammatory activity of the new compound was evaluated, and the results indicated that it exhibited superior activity compared to the standard, ibuprofen. The bio-functional hybrid compound underwent thorough detailed characterization utilizing 1H and 13C NMR, UV, and mass spectral analysis. Full article
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4 pages, 744 KiB  
Short Note
Ethyl 4-((11-(Hexylamino)-11-oxoundecyl)oxy)benzoate
by Jorge Jesús Montes-Patiño, Nancy Patricia Díaz-Zavala, Samuel Zapién-Castillo, Philippe J. Mésini, Jessica Ismalé Lozano-Navarro, Lorena Margarita Salas-Ordaz and Marco Antonio Aguirre-Lam
Molbank 2024, 2024(2), M1829; https://doi.org/10.3390/M1829 - 27 May 2024
Viewed by 743
Abstract
Ethyl 4-((11-(hexylamino)-11-oxoundecyl)oxy)benzoate was synthesized using 11-bromoundecanoic acid hexylamide and commercially available ethyl 4-hydroxybenzoate through a Williamson etherification synthesis. The structural characterization was performed using UV-Vis, FT-IR, 1H-NMR, 13C-NMR, and HRMS. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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6 pages, 1175 KiB  
Short Note
Hept-6-en-1-yl Furan-2-carboxylate
by Zhongwei Wang, Lin Song and Yukun Qin
Molbank 2024, 2024(2), M1828; https://doi.org/10.3390/M1828 - 27 May 2024
Viewed by 704
Abstract
This study aims to develop an efficient and green one-pot method for the synthesis of 6-en-1-yl furan-2-carboxylic acid heptyl ester. Initially, using furfural as the starting substrate, hept-6-en-1-yl furan-2-carboxylate was prepared using a one-pot method. This study developed a new experimental scheme for [...] Read more.
This study aims to develop an efficient and green one-pot method for the synthesis of 6-en-1-yl furan-2-carboxylic acid heptyl ester. Initially, using furfural as the starting substrate, hept-6-en-1-yl furan-2-carboxylate was prepared using a one-pot method. This study developed a new experimental scheme for preparing ester compounds, using cuprous chloride as a catalyst and tert butyl hydrogen peroxide as an oxidant to prepare furoic acid. Without the need for intermediate treatment, the target product can be directly obtained from furfural by adding 7-bromo-1-heptene, TBAB, and potassium carbonate. This method effectively utilizes furfural as a platform chemical, demonstrating its potential for synthesizing high-value chemicals. The entire synthesis process is simple and efficient, following the principles of green chemistry. Full article
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13 pages, 1848 KiB  
Communication
Synthesis and Antibacterial Studies of a New Au(III) Complex with 6-Methyl-2-Thioxo-2,3-Dihydropyrimidin-4(1H)-One
by Petya Marinova, Nikola Burdzhiev, Denica Blazheva and Aleksandar Slavchev
Molbank 2024, 2024(2), M1827; https://doi.org/10.3390/M1827 - 24 May 2024
Cited by 1 | Viewed by 835
Abstract
This article describes the synthesis of a new metal complex using 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one. The compound was analyzed using several methods, including determining its melting point and employing UV-Vis, IR, ATR, 1H NMR, HSQC, and Raman spectroscopy for the free ligand. The [...] Read more.
This article describes the synthesis of a new metal complex using 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one. The compound was analyzed using several methods, including determining its melting point and employing UV-Vis, IR, ATR, 1H NMR, HSQC, and Raman spectroscopy for the free ligand. The metal complex was formed by combining aqueous solutions of metal salts with the ligand dissolved in DMSO and water, along with NaOH in a metal-to-ligand-to-base ratio of 1:4:2. The NMR signals of the ligand were assigned using 1H-1H COSY, DEPT-135, HMBC, and HMQC spectra. Furthermore, the compound’s antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as yeasts, was assessed. Full article
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6 pages, 701 KiB  
Communication
Structural Modification of Epigallocatechin-3-gallate to (2R,3R)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-3-yl l-valinate in Four Steps
by Xiaoman Yu, Zimo Ren, Paolo Coghi and Jerome P. L. Ng
Molbank 2024, 2024(2), M1826; https://doi.org/10.3390/M1826 - 23 May 2024
Viewed by 725
Abstract
Tea is a daily drink for most people, and one of its major ingredients, epigallocatechin-3-gallate (EGCG), has been widely recognized as a potent antioxidant with diverse biological activities. However, its low stability and bioavailability hinder its further clinical applications. In this study, we [...] Read more.
Tea is a daily drink for most people, and one of its major ingredients, epigallocatechin-3-gallate (EGCG), has been widely recognized as a potent antioxidant with diverse biological activities. However, its low stability and bioavailability hinder its further clinical applications. In this study, we designed and synthesized a novel EGCG-valine derivative 4 by replacing the gallic acid with a valine moiety in four steps. The structural elucidation of derivative 4 was performed using NMR, IR, mass, and UV spectroscopies. Additionally, the physicochemical properties of 4 were predicted by SwissADME, showing improved drug-like parameters and intestinal absorption compared to the parent compound EGCG. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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8 pages, 1433 KiB  
Short Note
Methyl 6-Benzyl-3-Hydroxy-3,6-Dimethyl-1,2-Dioxane-4-Carboxylate
by Alexandre Benech, Omar Khoumeri, Christophe Curti and Patrice Vanelle
Molbank 2024, 2024(2), M1825; https://doi.org/10.3390/M1825 - 23 May 2024
Viewed by 714
Abstract
Plasmodium falciparum is a fast-evolving parasite responsible for the fatal disease malaria, making it crucial to renew our therapeutic arsenal. Modulating the artemisinin’s endoperoxide pharmacophore is a promising route to synthesizing new antimalarial derivatives. For the first step of our 20 mmol scale [...] Read more.
Plasmodium falciparum is a fast-evolving parasite responsible for the fatal disease malaria, making it crucial to renew our therapeutic arsenal. Modulating the artemisinin’s endoperoxide pharmacophore is a promising route to synthesizing new antimalarial derivatives. For the first step of our 20 mmol scale synthesis, catalyzed by manganese (III) acetylacetonate, we applied the conditions previously described in the literature to one of our low-yielding asymmetrically disubstituted alkenes, (2-methylallyl)benzene. Under conditions designed for alkyl derivatives, manganese (II) and (III) acetate catalyzed its peroxycyclization with methyl 3-oxobutanoate to a 1,2-dioxane ring in the presence of oxygen from air at room temperature with a 36% yield, while an oxygen atmosphere, as described in the literature, decreased the yield to 7%. Finally, under conditions designed for aryl derivatives, the yield was reduced to 30%, showing that methylallyl derivatives have an intermediate reactivity that needs further optimization to produce 1,2-dioxane ring by manganese catalyzation in good yields. This work characterizes the product obtained and discusses the most suitable reaction conditions. Full article
(This article belongs to the Collection Molecules from Catalytic Processes)
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8 pages, 2332 KiB  
Communication
(Hetero)Arene Ring-Fused [1,2,4]Triazines
by Mahshid Teymouri, Anna Pietrzak and Paulina Bartos
Molbank 2024, 2024(2), M1824; https://doi.org/10.3390/M1824 - 20 May 2024
Viewed by 881
Abstract
Synthetic access to a five (hetero)arene ring-fused 3-phenyl[1,2,4]triazines is described. The resulting compounds were characterized via 1H and 13C NMR, IR, UV–vis spectroscopy and HRMS. The structure of 3-phenyl[1,2,4]triazino[5,6-c]quinoline was unambiguously confirmed by single crystal XRD. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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8 pages, 2707 KiB  
Communication
4-(Tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline
by Bradley B. Garrison, Joseph E. Duhamel, Nehemiah Antoine, Steven J. K. Symes, Kyle A. Grice, Colin D. McMillen and Jared A. Pienkos
Molbank 2024, 2024(2), M1823; https://doi.org/10.3390/M1823 - 17 May 2024
Viewed by 1208
Abstract
4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal [...] Read more.
4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline was prepared in a 63% yield utilizing a C–F activation strategy from a mixture of 4-(trifluoromethyl)aniline, 4-methylpyrazole, and KOH in dimethylsulfoxide (DMSO). The identity of the product was confirmed by nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and single-crystal analysis. An analysis of crystals grown from the layering method (CH2Cl2/acetone/pentane) indicated two distinct polymorphs of the title compound. Moreover, density functional theory calculations utilizing the MN15L density functional and the def2-TZVP basis set indicated that 4-(tris(4-methyl-1H-pyrazol-1-yl)methyl)aniline forms with similar energetics to the previously reported unmethylated analog. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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8 pages, 1460 KiB  
Short Note
11-Hydroxy-7-Methoxy-2,8-Dimethyltetracene-5,12-Dione
by Rishi Vachaspathy Astakala, Gagan Preet, Ahlam Haj Hasan, Ria Desai, Juan A. Asenjo, Barbara Andrews, William T. A. Harrison, Rainer Ebel and Marcel Jaspars
Molbank 2024, 2024(2), M1822; https://doi.org/10.3390/M1822 - 14 May 2024
Viewed by 1320
Abstract
Microorganisms are a valuable source of pharmaceutically active chemicals, serving as scaffolds for synthesis as well as lead structures. Investigating novel biomes frequently yields intriguing chemistry; the Atacama Desert in Chile is one such example. This study reports the isolation of a new [...] Read more.
Microorganisms are a valuable source of pharmaceutically active chemicals, serving as scaffolds for synthesis as well as lead structures. Investigating novel biomes frequently yields intriguing chemistry; the Atacama Desert in Chile is one such example. This study reports the isolation of a new reduced anthracycline-related compound from the Atacama Desert-derived bacterium Saccharothrix S26. Structural characterisation was achieved by one-dimensional and two-dimensional NMR, HR-LCMS, and X-ray crystallography. The compound was tested against the ESKAPE pathogens, bovine mastitis-related pathogens, and the fungal strain Cryptococcus neoformans, but no antimicrobial activity was observed. Full article
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8 pages, 1286 KiB  
Communication
Adamantylated Calix[4]arenes Bearing CuAAC-Ready 2-Azidoethyl or Propargyl Functionalities
by Alexander Gorbunov, Maria Malakhova, Stanislav Bezzubov, Ivan Lentin, Vladimir Kovalev and Ivan Vatsouro
Molbank 2024, 2024(2), M1821; https://doi.org/10.3390/M1821 - 11 May 2024
Viewed by 1235
Abstract
1,3-Alternate calix[4]arenes were prepared, having bulky adamantyl groups in the p-positions of all four aromatic units of the macrocycles and pairs of propargyl or 2-azidoethyl groups alternating with n-propyl groups at the phenol oxygen atoms. The step-wise syntheses were carried out [...] Read more.
1,3-Alternate calix[4]arenes were prepared, having bulky adamantyl groups in the p-positions of all four aromatic units of the macrocycles and pairs of propargyl or 2-azidoethyl groups alternating with n-propyl groups at the phenol oxygen atoms. The step-wise syntheses were carried out through a selective distal alkylation of the parent p-adamantylcalix[4]arene with propargyl bromide or 1,2-dibromoethane, resulting in calix[4]arenes bearing pairs of propargyl or 2-bromoethyl groups at their narrow rims. The bromine atoms were replaced by azide groups, and then both calix[4]arene diethers were exhaustively alkylated at the remaining OH-groups with 1-iodopropane under stereoselective conditions to fix the macrocycles in an 1,3-alternate shape. The structures of the prepared p-adamantylcalix[4]arenes were confirmed by NMR and HRMS data, and, for the 1,3-alternate dipropargyl ether, the X-ray diffraction data were also collected. Preliminary data on the reactivity of the prepared calixarenes under the CuAAC conditions suggested a strong steric hampering created by the adamantane units nearby the reacting alkyne or azide groups that affected the outcome of the two-fold cycloaddition involving the calixarene bis(azides) or bis(alkynes) as complementary partners. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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6 pages, 663 KiB  
Short Note
8(S)-[(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyloxy]-3,4-dihydro-2H-[1,4]dithiepino[2,3-c]furan-6(8H)-one
by Alsu M. Khabibrakhmanova, Enze S. Rabbanieva, Darya P. Gerasimova, Liliya Z. Latypova and Almira R. Kurbangalieva
Molbank 2024, 2024(2), M1820; https://doi.org/10.3390/M1820 - 11 May 2024
Viewed by 948
Abstract
The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an [...] Read more.
The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an optically active fused bicyclic sulfur heterocycle, possessing 1,4-dithiepine and unsaturated γ-lactone moieties. The studied reaction follows an unexpected pathway in a basic medium with the thiolate–thiolate exchange. The structure of the novel heterocycle of the 1,4-dithiepinofuranone series is characterized by single-crystal X-ray diffraction. Full article
(This article belongs to the Collection Heterocycle Reactions)
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7 pages, 1898 KiB  
Communication
Synthesis and Structure of a Coordination Polymer of Ni(II) with 2-(4-Bromophenoxy)acetohydrazide
by Оlena Martsynko, Mariia Nesterkina, Оlena Finik, Kyrylo Tsymbaliuk, Viktoriya Dyakonenko, Svitlana Shishkina and Iryna Kravchenko
Molbank 2024, 2024(2), M1819; https://doi.org/10.3390/M1819 - 8 May 2024
Cited by 1 | Viewed by 1474
Abstract
The coordination compound [NiCl2L(2-PrOH)]n (where L is 2-(4-bromophenoxy)acetohydrazide; 2-PrOH is isopropanol) was obtained for the first time. The complex was characterized by means of elemental analyses, molar conductance, thermogravimetric analysis, IR spectroscopy, and single crystal X-ray diffraction analysis. It was [...] Read more.
The coordination compound [NiCl2L(2-PrOH)]n (where L is 2-(4-bromophenoxy)acetohydrazide; 2-PrOH is isopropanol) was obtained for the first time. The complex was characterized by means of elemental analyses, molar conductance, thermogravimetric analysis, IR spectroscopy, and single crystal X-ray diffraction analysis. It was determined that the coordination compound exhibits a polymeric structure. The complexing agent is six-coordinated, and its distorted octahedron forms due to the bidentate coordination of 2-(4-bromophenoxy)acetohydrazide through the carbonyl oxygen atom and the amine nitrogen. The oxygen of the molecule of isopropanol, the chlorine atom, and two chlorine atoms serve as bridges between two metal atoms. Full article
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6 pages, 911 KiB  
Short Note
(E)-1-(5-(Hydroxymethyl) furan-2-yl)-4,4-dimethylpent-1-en-3-one
by Zhongwei Wang, Luxiao Zhou, Peng He and Yukun Qin
Molbank 2024, 2024(2), M1818; https://doi.org/10.3390/M1818 - 7 May 2024
Viewed by 1258
Abstract
This study presents a novel approach in the realm of catalytic organic synthesis by integrating biomass catalytic conversion with organic synthesis techniques. Utilizing N-acetylglucosamine as the primary feedstock, the first phase of the research involves its catalytic transformation into 5-hydroxymethylfurfural (HMF). The [...] Read more.
This study presents a novel approach in the realm of catalytic organic synthesis by integrating biomass catalytic conversion with organic synthesis techniques. Utilizing N-acetylglucosamine as the primary feedstock, the first phase of the research involves its catalytic transformation into 5-hydroxymethylfurfural (HMF). The subsequent phase employs a condensation reaction between HMF and 3,3-Dimethyl-2-butanone to synthesize a new compound, (E)-1-(5-(hydroxymethyl) furan-2-yl)-4,4-dimethylpent-1-en-3-one. This two-step process not only demonstrates the feasibility of converting biomass into valuable chemical precursors but also exemplifies the synthesis of novel compounds through green chemistry principles. The successful execution of this methodology offers fresh insights and opens new avenues for advancements in catalytic organic synthesis, emphasizing sustainability and efficiency. Full article
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8 pages, 996 KiB  
Short Note
4,4’-(Thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(1-methyl-1-pyridinium) Iodide
by Lorenza Romagnoli, Alessandro Latini and Andrea D’Annibale
Molbank 2024, 2024(2), M1817; https://doi.org/10.3390/M1817 - 6 May 2024
Viewed by 1034
Abstract
In the vast field of organic functional materials, viologens are widely recognized as an extremely versatile family of substances, due in part to the possibility of extending conjugation between the terminal pyridinium rings, for instance through the insertion of additional aromatic moieties. In [...] Read more.
In the vast field of organic functional materials, viologens are widely recognized as an extremely versatile family of substances, due in part to the possibility of extending conjugation between the terminal pyridinium rings, for instance through the insertion of additional aromatic moieties. In this work, a new, extended viologen with a thiophene core and two acetylene bonds is presented. It was synthesized through a straightforward route, using well-established Sonogashira coupling reactions, and its optical properties were investigated by UV–visible absorption and fluorescence spectroscopy, revealing a very interesting material for diverse fluorescence-related applications. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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5 pages, 860 KiB  
Short Note
Di-µ-(1-(3-(1H-imidazol-1-yl)propyl)-2-methyl-4-oxo-1,4-dihydropyridin-3-olate)-bis[(η5-pentamethylcyclopentadienyl)iridium(III)] Chloride
by Ilya A. Shutkov, Nikolai A. Melnichuk, Konstantin A. Lyssenko, Nataliya E. Borisova, Olga N. Kovaleva and Alexey A. Nazarov
Molbank 2024, 2024(2), M1816; https://doi.org/10.3390/M1816 - 5 May 2024
Viewed by 1371
Abstract
A metallacyclic maltol-tethered organometallic Ir(III) half-sandwich complex was synthesized as an analog of the ruthenium anticancer complexes (RAPTA/RAED) to evaluate its in vitro antiproliferative activity against various human cancer cell lines. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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6 pages, 1019 KiB  
Communication
Synthesis and Spectroscopic Study of New 1H-1-Alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4]triazoles
by Ion Burcă, Valentin Badea, Vasile-Nicolae Bercean and Francisc Péter
Molbank 2024, 2024(2), M1815; https://doi.org/10.3390/M1815 - 24 Apr 2024
Viewed by 905
Abstract
The nitrosation of 1H-1-alkyl-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazoles leads to new 1H-1-alkyl-6-methyl-7-nitroso-3-phenylpyrazolo[5,1-c][1,2,4] triazoles that react in acidic media, giving rise to 1H-1-alkyl-7-hydroxyimino-6-methyl-3-phenylpyrazolo[5,1-c][1,2,4]triazolium salts. These compounds were characterized by FT-IR, UV-Vis, 1H-NMR, 13C-NMR, and 15N-NMR spectroscopic techniques. Full article
(This article belongs to the Collection Heterocycle Reactions)
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6 pages, 1469 KiB  
Short Note
5,6-Diphenyl-1,3,4,7-tetra-p-tolyl-1,3,3a,7a-tetrahydropentaleno[1,2-c]furan
by Shu-Kai Chen, Yi-Hung Liu and Shiuh-Tzung Liu
Molbank 2024, 2024(2), M1814; https://doi.org/10.3390/M1814 - 24 Apr 2024
Viewed by 866
Abstract
The reaction of (Z)-5-phenyl-1,3-di-p-tolylpent-2-en-4-yn-1-ol (1) with trimethylsilyl chloride in dichloromethane at ambient temperature gave a dimeric ether compound 2 in 30% yield. Subsequently, heating 2 in toluene under refluxing temperature rendered the title compound quantitatively. The structure [...] Read more.
The reaction of (Z)-5-phenyl-1,3-di-p-tolylpent-2-en-4-yn-1-ol (1) with trimethylsilyl chloride in dichloromethane at ambient temperature gave a dimeric ether compound 2 in 30% yield. Subsequently, heating 2 in toluene under refluxing temperature rendered the title compound quantitatively. The structure of this tricyclic-fused compound was characterized using NMR, mass spectroscopy, and X-ray crystallography. This unique linear tricyclic fused furan framework is reported for the first time. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

5 pages, 946 KiB  
Short Note
5,5′-Thiobis(3-bromoisothiazole-4-carbonitrile)
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2024, 2024(2), M1813; https://doi.org/10.3390/M1813 - 24 Apr 2024
Viewed by 879
Abstract
The reaction of sodium 2,2-dicyanoethene-1,1-bis(thiolate) with bromine (2 equiv.) in CCl4 gave 3,5-dibromoisothiazole-3-carbonitrile and 5,5′-thiobis(3-bromoisothiazole-4-carbonitrile) in 7% and 18% yields, respectively. The latter novel compound was fully characterized. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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8 pages, 1315 KiB  
Short Note
2S-(1RS-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine
by Angelica Artasensi and Laura Fumagalli
Molbank 2024, 2024(2), M1812; https://doi.org/10.3390/M1812 - 24 Apr 2024
Viewed by 1048
Abstract
In medicinal chemistry, the precise configuration of molecules is a crucial determinant of their pharmacological properties. Hence, the introduction of a new chiral center during the synthetic pathway involves the assignment of configuration. Herein we assign, by means of molecular modeling 1H [...] Read more.
In medicinal chemistry, the precise configuration of molecules is a crucial determinant of their pharmacological properties. Hence, the introduction of a new chiral center during the synthetic pathway involves the assignment of configuration. Herein we assign, by means of molecular modeling 1H and 2D Nuclear Overhauser Effect NMR techniques, the configuration of the two diastereomers 2S-(1R-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine and 2S-(1S-benzyloxy-hex-5-enyl)-2,3-dihydro-1,4-benzodioxine, which are useful to synthetize analogs of the potent and highly selective dipeptidyl peptidase IV and carbonic anhydrase inhibitor recently published. Full article
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5 pages, 552 KiB  
Short Note
Chloro(η2,η2-cycloocta-1,5-diene){1-benzyl-3-[(S)-2-hydroxy-1-methylethyl]benzimidazol-2-ylidene}rhodium(I)
by Satoshi Sakaguchi and Shogo Matsuo
Molbank 2024, 2024(2), M1811; https://doi.org/10.3390/M1811 - 19 Apr 2024
Viewed by 885
Abstract
Previously, we demonstrated the synthesis of a well-defined hydroxyalkyl-functionalized N-heterocyclic carbene (NHC)/Ru(II) complex through the transmetalation reaction between [RuCl2(p-cymene)]2 and the corresponding NHC/Ag(I) complex derived from a chiral benzimidazolium salt using the Ag2O method. In [...] Read more.
Previously, we demonstrated the synthesis of a well-defined hydroxyalkyl-functionalized N-heterocyclic carbene (NHC)/Ru(II) complex through the transmetalation reaction between [RuCl2(p-cymene)]2 and the corresponding NHC/Ag(I) complex derived from a chiral benzimidazolium salt using the Ag2O method. In this study, we successfully synthesized [RhX(cod)(NHC)] complexes through a one-pot deprotonation route. The hydroxyalkyl-substituted benzimidazolium salt reacted with [Rh(OH)(cod)]2 in THF at room temperature, affording the corresponding monodentate NHC/Rh(I) complex in nearly quantitative yield. The rhodium complex was characterized using NMR, HRMS measurement, and elemental analysis. Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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5 pages, 640 KiB  
Short Note
Chloro(η2,η2-cycloocta-1,5-diene){1-[(2-[(S)-1-(hydroxymethyl)-3-methylbutyl]amino)-2-oxoethyl]-3-(1-naphthalenylmethyl)benzimidazol-2-ylidene}rhodium(I)
by Satoshi Sakaguchi and Shogo Matsuo
Molbank 2024, 2024(2), M1810; https://doi.org/10.3390/M1810 - 19 Apr 2024
Viewed by 978
Abstract
Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]2 (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H [...] Read more.
Commercially available and air- and moisture-stable rhodium complex [Rh(OH)(cod)]2 (2) was utilized in the synthesis of [RhX(cod)(NHC)] (3). The presence of an OH group in complex 2 serves as an internal base, facilitating the deprotonation of the C–H bond of the azolium ring in the hydroxyamide-substituted benzimidazolium salt 1. This reaction between 1 and 2 proceeded in THF at room temperature without temperature control, affording the desired NHC/Rh complex 3 in excellent yield. The characterization of complex 3 was accomplished through NMR and HRMS analyses, revealing its existence as a diastereomeric mixture of two NHC/Rh complexes. Furthermore, its catalytic performance was briefly evaluated in the reaction between 2-naphthaldehyde (5) and phenylboronic acid (6). Full article
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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