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1802 KiB

Open AccessCommunication

Optimizing the Readout of Lanthanide-DOTA Complexes for the Detection of Ligand-Bound Copper(I)

by Jill R. Hanna, Christopher Allan, Charlotte Lawrence, Odile Meyer, Neil D. Wilson and Alison N. Hulme

Molecules 2017, 22(5), 802; https://doi.org/10.3390/molecules22050802 - 14 May 2017

Cited by 13 | Viewed by 8616

Abstract

The CuAAC ‘click’ reaction was used to couple alkyne-functionalized lanthanide-DOTA complexes to a range of fluorescent antennae. Screening of the antenna components was aided by comparison of the luminescent output of the resultant sensors using data normalized to account for reaction conversion as [...] Read more.

The CuAAC ‘click’ reaction was used to couple alkyne-functionalized lanthanide-DOTA complexes to a range of fluorescent antennae. Screening of the antenna components was aided by comparison of the luminescent output of the resultant sensors using data normalized to account for reaction conversion as assessed by IR. A maximum 82-fold enhanced signal:background luminescence output was achieved using a Eu(III)-DOTA complex coupled to a coumarin-azide, in a reaction which is specific to the presence of copper(I). This optimized complex provides a new lead design for lanthanide-DOTA complexes which can act as irreversible ‘turn-on’ catalytic sensors for the detection of ligand-bound copper(I). Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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1356 KiB

Open AccessArticle

C-C Coupling Reactions between Benzofurazan Derivatives and 1,3-Diaminobenzenes

by Gabriele Micheletti, Silvia Bordoni, Elena Chugunova and Carla Boga

Molecules 2017, 22(5), 684; https://doi.org/10.3390/molecules22050684 - 26 Apr 2017

Cited by 6 | Viewed by 6059

Abstract

Aromatic substitution reactions between 1,3-diaminobenzene and chloronitrobenzofurazan derivatives have never been reported so far. The aim of the current study was to synthesize novel electron-donor and -acceptor architectures of interest in applied fields and to provide new insights on the nucleophilic behavior of [...] Read more.

Aromatic substitution reactions between 1,3-diaminobenzene and chloronitrobenzofurazan derivatives have never been reported so far. The aim of the current study was to synthesize novel electron-donor and -acceptor architectures of interest in applied fields and to provide new insights on the nucleophilic behavior of 1,3-diaminobenzenes. The reaction of 1,3-dipiperidinyl-, 1,3-dimorpholinyl-, 1,3-dipyrrolidinyl-, or 1,3-dimethylamino-benzene with 7-chloro-4,6-dinitrobenzofuroxan or with a series of chloro-nitrobenzofurazans has been carried out in mild conditions. The partners reactivity has been investigated by monitoring the reaction course through ¹H-NMR spectroscopy. The reaction occurred in a regioselective way, providing in good yields the novel C-C coupling compounds. Indications on the reactivity behavior for the studied nucleophiles have been relieved. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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3315 KiB

Open AccessArticle

One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors

by Thomas Pesnot, Markus C. Gershater, Martin Edwards, John M. Ward and Helen C. Hailes

Molecules 2017, 22(4), 626; https://doi.org/10.3390/molecules22040626 - 12 Apr 2017

Cited by 6 | Viewed by 5357

Abstract

Polysubstituted pyridinium salts are valuable pharmacophores found in many biologically active molecules. Their synthesis typically involves the use of multistep procedures or harsh reaction conditions. Here, we report water-based phosphate mediated reaction conditions that promote the condensation of arylacetaldehydes with amines to give [...] Read more.

Polysubstituted pyridinium salts are valuable pharmacophores found in many biologically active molecules. Their synthesis typically involves the use of multistep procedures or harsh reaction conditions. Here, we report water-based phosphate mediated reaction conditions that promote the condensation of arylacetaldehydes with amines to give 1,3,5-pyridinium salts. The reaction, carried out at pH 6, provides conditions suitable for the use of less stable aldehydes and amines in this Chichibabin pyridine condensation. The evaluation of selected 1,3,5-trisubstituted pyridinium salts highlighted that they can inhibit the growth of S. aureus in the low μg/mL range. The synthetic accessibility of these compounds and preliminary growth inhibition data may pave the way towards the discovery of new anti-bacterials based on the 1,3,5-trisubstituted pyridinium scaffold. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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1262 KiB

Open AccessCommunication

Chemical Synthesis and Characterization of an Equinatoxin II(1–85) Analogue

by John A. Karas, Marc-Antoine Sani and Frances Separovic

Molecules 2017, 22(4), 559; https://doi.org/10.3390/molecules22040559 - 30 Mar 2017

Cited by 2 | Viewed by 5047

Abstract

The chemical synthesis of an 85 residue analogue of the pore-forming protein, Equinatoxin II (EqtII), was achieved. Peptide precursors with over 40 residues were assembled by solid phase synthesis. The EqtII(1–46) fragment was modified to the reactive C-terminal thioester and native chemical ligation [...] Read more.

The chemical synthesis of an 85 residue analogue of the pore-forming protein, Equinatoxin II (EqtII), was achieved. Peptide precursors with over 40 residues were assembled by solid phase synthesis. The EqtII(1–46) fragment was modified to the reactive C-terminal thioester and native chemical ligation was performed with the A47C mutated EqtII(47–85) peptide to form the EqtII(1–85) analogue. Circular dichroism spectroscopy indicated that the N-terminal domain of EqtII(1–46) and EqtII(1–85) maintains predominantly an α-helical structure in solution and also in the presence of lipid micelles. This demonstrates the feasibility of assembling the full 179 residue protein EqtII via chemical means. Site-specific isotopic labels could be incorporated for structural studies in membranes by solid-state NMR spectroscopy. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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1147 KiB

Open AccessCommunication

Revision of the Structure of Acremine P from a Marine-Derived Strain of Acremonium persicinum

by Mary J. Garson, Warren Hehre, Gregory K. Pierens and Suciati

Molecules 2017, 22(4), 521; https://doi.org/10.3390/molecules22040521 - 24 Mar 2017

Cited by 13 | Viewed by 5215

Abstract

The previously published structure of the fungal metabolite acremine P is revised by re-evaluation of chemical shift values and NOESY data, and by DFT calculations. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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1456 KiB

Open AccessArticle

Synthesis of Novel Saccharin Derivatives

by Gregory M. Rankin and Sally-Ann Poulsen

Molecules 2017, 22(4), 516; https://doi.org/10.3390/molecules22040516 - 23 Mar 2017

Cited by 4 | Viewed by 7353

Abstract

The synthesis of saccharin (1,2-benzisothiazol-3-one-1,1-dioxide) derivatives substituted on the benzene ring has seen limited development despite the longevity of this compound’s use as an artificial sweetener. This type of saccharin derivative would however present attractive properties for the development of new bioactive, drug-like [...] Read more.

The synthesis of saccharin (1,2-benzisothiazol-3-one-1,1-dioxide) derivatives substituted on the benzene ring has seen limited development despite the longevity of this compound’s use as an artificial sweetener. This type of saccharin derivative would however present attractive properties for the development of new bioactive, drug-like small molecule compounds. Here we report the derivatisation of the benzene ring of saccharin using Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC) to synthesise a diverse library of novel saccharin-1,2,3-triazole conjugates. All library compounds retain the capability for interactions with biomolecules via the unmodified sulfonamide and lactam groups of the parent saccharin core heterocycle. The compounds also encompass alternate orientations of the 1,2,3-triazole heterocycle, thus further adding diversity to the potential hydrogen bonding interactions of these compounds with biomolecules of therapeutic interest. Our findings demonstrate that specifically functionalized derivatives of saccharin may be prepared from either saccharin azide or saccharin alkyne building blocks in high yield using CuAAC. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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2247 KiB

Open AccessArticle

Three-Component Reaction of Benzylamines, Diethyl Phosphite and Triethyl Orthoformate: Dependence of the Reaction Course on the Structural Features of the Substrates and Reaction Conditions

by Patrycja Miszczyk, Ilona Turowska-Tyrk, Paweł Kafarski and Ewa Chmielewska

Molecules 2017, 22(3), 450; https://doi.org/10.3390/molecules22030450 - 11 Mar 2017

Cited by 4 | Viewed by 7250

Abstract

The reaction between benzyl amines, triethyl orthoformate, and diethyl phosphite affords either bisphosphonic (compound 1) or N-benzylaminobenzylphosphonic (compound 2) acid depending on the reaction conditions. The final output of the reaction can be manipulated by the choice of reaction conditions, [...] Read more.

The reaction between benzyl amines, triethyl orthoformate, and diethyl phosphite affords either bisphosphonic (compound 1) or N-benzylaminobenzylphosphonic (compound 2) acid depending on the reaction conditions. The final output of the reaction can be manipulated by the choice of reaction conditions, particularly the molar ratio of substrates. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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5398 KiB

Open AccessArticle

Antiproliferative, Cytotoxic, and Apoptotic Activity of Steroidal Oximes in Cervicouterine Cell Lines

by Luis Sánchez-Sánchez, María Guadalupe Hernández-Linares, María L. Escobar, Hugo López-Muñoz, Edgar Zenteno, María A. Fernández-Herrera, Gabriel Guerrero-Luna, Alan Carrasco-Carballo and Jesús Sandoval-Ramírez

Molecules 2016, 21(11), 1533; https://doi.org/10.3390/molecules21111533 - 14 Nov 2016

Cited by 25 | Viewed by 6955

Abstract

Steroidal sapogenins have shown antiproliferative effects against several tumor cell lines; and their effects on human cancer cells are currently under study. Changes in the functionality on the steroidal structure make it possible to modify the biological activity of compounds. Herein, we report [...] Read more.

Steroidal sapogenins have shown antiproliferative effects against several tumor cell lines; and their effects on human cancer cells are currently under study. Changes in the functionality on the steroidal structure make it possible to modify the biological activity of compounds. Herein, we report the synthesis and in vitro antitumor activity of two steroidal oxime compounds on cervical cancer cells. These derivatives were synthesized from the steroidal sapogenin diosgenin in good yields. The in vitro assays show that the steroidal oximes show significant antiproliferative activity compared to the one observed for diosgenin. Cell proliferation, cell death, and the cytotoxic effects were determined in both cervical cancer cells and human lymphocytes. The cancer cells showed apoptotic morphology and an increased presence of active caspase-3, providing the notion of a death pathway in the cell. Significantly, the steroidal oximes did not exert a cytotoxic effect on lymphocytes. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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Review

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11894 KiB

Open AccessFeature PaperReview

β-Formyl- and β-Vinylporphyrins: Magic Building Blocks for Novel Porphyrin Derivatives

by Ana F. R. Cerqueira, Nuno M. M. Moura, Vanda Vaz Serra, M. Amparo F. Faustino, Augusto C. Tomé, José A. S. Cavaleiro and M. Graça P. M. S. Neves

Molecules 2017, 22(8), 1269; https://doi.org/10.3390/molecules22081269 - 29 Jul 2017

Cited by 29 | Viewed by 9519

Abstract

Porphyrins bearing formyl or vinyl groups have been explored as starting materials to prepare new compounds with adequate features for different applications. In this review it is discussed mainly synthetic strategies based on the reaction of meso-tetraarylporphyrins bearing those groups at β-pyrrolic [...] Read more.

Porphyrins bearing formyl or vinyl groups have been explored as starting materials to prepare new compounds with adequate features for different applications. In this review it is discussed mainly synthetic strategies based on the reaction of meso-tetraarylporphyrins bearing those groups at β-pyrrolic positions. The use of some of the obtained porphyrin derivatives for further transformations, namely via pericyclic reactions, is also highlighted. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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1450 KiB

Open AccessReview

Chemical Methods to Knock Down the Amyloid Proteins

by Na Gao, Yong-Xiang Chen, Yu-Fen Zhao and Yan-Mei Li

Molecules 2017, 22(6), 916; https://doi.org/10.3390/molecules22060916 - 1 Jun 2017

Cited by 14 | Viewed by 7311

Abstract

Amyloid proteins are closely related with amyloid diseases and do tremendous harm to human health. However, there is still a lack of effective strategies to treat these amyloid diseases, so it is important to develop novel methods. Accelerating the clearance of amyloid proteins [...] Read more.

Amyloid proteins are closely related with amyloid diseases and do tremendous harm to human health. However, there is still a lack of effective strategies to treat these amyloid diseases, so it is important to develop novel methods. Accelerating the clearance of amyloid proteins is a favorable method for amyloid disease treatment. Recently, chemical methods for protein reduction have been developed and have attracted much attention. In this review, we focus on the latest progress of chemical methods that knock down amyloid proteins, including the proteolysis-targeting chimera (PROTAC) strategy, the “recognition-cleavage” strategy, the chaperone-mediated autophagy (CMA) strategy, the selectively light-activatable organic and inorganic molecules strategy and other chemical strategies. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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Open AccessReview

Exploring Anti-Prion Glyco-Based and Aromatic Scaffolds: A Chemical Strategy for the Quality of Life

by María Teresa Blázquez-Sánchez, Ana M. De Matos and Amélia P. Rauter

Molecules 2017, 22(6), 864; https://doi.org/10.3390/molecules22060864 - 24 May 2017

Cited by 9 | Viewed by 7322

Abstract

Prion diseases are fatal neurodegenerative disorders caused by protein misfolding and aggregation, affecting the brain progressively and consequently the quality of life. Alzheimer’s is also a protein misfolding disease, causing dementia in over 40 million people worldwide. There are no therapeutics able to [...] Read more.

Prion diseases are fatal neurodegenerative disorders caused by protein misfolding and aggregation, affecting the brain progressively and consequently the quality of life. Alzheimer’s is also a protein misfolding disease, causing dementia in over 40 million people worldwide. There are no therapeutics able to cure these diseases. Cellular prion protein is a high-affinity binding partner of amyloid β (Aβ) oligomers, the most toxic species in Alzheimer’s pathology. These findings motivate the development of new chemicals for a better understanding of the events involved. Disease control is far from being reached by the presently known therapeutics. In this review we describe the synthesis and mode of action of molecular entities with intervention in prion diseases’ biological processes and, if known, their role in Alzheimer’s. A diversity of structures is covered, based on glycans, steroids and terpenes, heterocycles, polyphenols, most of them embodying aromatics and a structural complexity. These molecules may be regarded as chemical tools to foster the understanding of the complex mechanisms involved, and to encourage the scientific community towards further developments for the cure of these devastating diseases. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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Open AccessReview

Applications of Gold Nanoparticles in Nanomedicine: Recent Advances in Vaccines

by Sónia Alexandra Correia Carabineiro

Molecules 2017, 22(5), 857; https://doi.org/10.3390/molecules22050857 - 22 May 2017

Cited by 105 | Viewed by 12722

Abstract

Nowadays, gold is used in (nano-)medicine, usually in the form of nanoparticles, due to the solid proofs given of its therapeutic effects on several diseases. Gold also plays an important role in the vaccine field as an adjuvant and a carrier, reducing toxicity, [...] Read more.

Nowadays, gold is used in (nano-)medicine, usually in the form of nanoparticles, due to the solid proofs given of its therapeutic effects on several diseases. Gold also plays an important role in the vaccine field as an adjuvant and a carrier, reducing toxicity, enhancing immunogenic activity, and providing stability in storage. An even brighter golden future is expected for gold applications in this area. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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17924 KiB

Open AccessReview

Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry

by Felipe Cesar Sousa e Silva, Anthony F. Tierno and Sarah E. Wengryniuk

Molecules 2017, 22(5), 780; https://doi.org/10.3390/molecules22050780 - 12 May 2017

Cited by 55 | Viewed by 14888

Abstract

Over the last 20 years, high valent metal complexes have evolved from mere curiosities to being at the forefront of modern catalytic method development. This approach has enabled transformations complimentary to those possible via traditional manifolds, most prominently carbon-heteroatom bond formation. Key to [...] Read more.

Over the last 20 years, high valent metal complexes have evolved from mere curiosities to being at the forefront of modern catalytic method development. This approach has enabled transformations complimentary to those possible via traditional manifolds, most prominently carbon-heteroatom bond formation. Key to the advancement of this chemistry has been the identification of oxidants that are capable of accessing these high oxidation state complexes. The oxidant has to be both powerful enough to achieve the desired oxidation as well as provide heteroatom ligands for transfer to the metal center; these heteroatoms are often subsequently transferred to the substrate via reductive elimination. Herein we will review the central role that hypervalent iodine reagents have played in this aspect, providing an ideal balance of versatile reactivity, heteroatom ligands, and mild reaction conditions. Furthermore, these reagents are environmentally benign, non-toxic, and relatively inexpensive compared to other inorganic oxidants. We will cover advancements in both catalysis and high valent complex isolation with a key focus on the subtle effects that oxidant choice can have on reaction outcome, as well as limitations of current reagents. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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6174 KiB

Open AccessReview

Recent Advances in Cyanamide Chemistry: Synthesis and Applications

by M. R. Ranga Prabhath, Luke Williams, Shreesha V. Bhat and Pallavi Sharma

Molecules 2017, 22(4), 615; https://doi.org/10.3390/molecules22040615 - 12 Apr 2017

Cited by 59 | Viewed by 13349

Abstract

The application of alkyl and aryl substituted cyanamides in synthetic chemistry has diversified multi-fold in recent years. In this review, we discuss recent advances (since 2012) in the chemistry of cyanamides and detail their application in cycloaddition chemistry, aminocyanation reactions, as well as [...] Read more.

The application of alkyl and aryl substituted cyanamides in synthetic chemistry has diversified multi-fold in recent years. In this review, we discuss recent advances (since 2012) in the chemistry of cyanamides and detail their application in cycloaddition chemistry, aminocyanation reactions, as well as electrophilic cyanide-transfer agents and their unique radical and coordination chemistry. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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4732 KiB

Open AccessFeature PaperReview

Direct Substitution of Alcohols in Pure Water by Brønsted Acid Catalysis

by Rosa Ortiz and Raquel P. Herrera

Molecules 2017, 22(4), 574; https://doi.org/10.3390/molecules22040574 - 1 Apr 2017

Cited by 28 | Viewed by 8516

Abstract

With the increasing concern for sustainability, the use of environmentally friendly media to perform chemical processes has attracted the attention of many research groups. Among them, the use of water, as the unique solvent for reactions, is currently an active area of research. [...] Read more.

With the increasing concern for sustainability, the use of environmentally friendly media to perform chemical processes has attracted the attention of many research groups. Among them, the use of water, as the unique solvent for reactions, is currently an active area of research. One process of particular interest is the direct nucleophilic substitution of an alcohol avoiding its preliminary transformation into a good leaving group, since one of the by-products in this approach would be water. The direct substitution of allylic, benzylic, and tertiary alcohols has been achieved through S_N1-type reactions with catalytic amounts of Brønsted or Lewis acids; however, organic solvents are often required. In this review, the pioneering S_N1 approaches performed in pure water and in the absence of a metal based Lewis acid are compiled and discussed. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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817 KiB

Open AccessFeature PaperReview

Synthesis of Substituted α-Trifluoromethyl Piperidinic Derivatives

by Sarah Rioton, Domingo Gomez Pardo and Janine Cossy

Molecules 2017, 22(3), 483; https://doi.org/10.3390/molecules22030483 - 19 Mar 2017

Cited by 8 | Viewed by 7249

Abstract

A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives [...] Read more.

A comprehensive survey of pathways leading to the generation of α-trifluoromethyl monocyclic piperidinic derivatives is provided (65 references). These compounds have been synthesized either from 6-membered rings e.g., pipecolic acid or lactam derivatives by introduction a trifluoromethyl group, from pyridine or pyridinone derivatives by reduction, and from 5-membered rings e.g., prolinol derivatives by ring expansion, from linear amines by cyclization or from dienes/dienophiles by [4 + 2]-cycloaddition. Full article

(This article belongs to the Special Issue Women in Organic Chemistry)

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