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A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 26916

Special Issue Editors

Prof. Dr. William D. Lubell

E-Mail Website
Guest Editor
Department of Chemistry, University of Montreal, Montreal, QC H3C 3J7, Canada
Interests: peptide science; chemical biology; conformational restriction; amino acid; polyamide and heterocycle synthesis; medicinal chemistry; diversity-oriented synthesis; peptidomimetic; drug discovery
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Bradley L. Merner

E-Mail Website
Assistant Guest Editor
Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36830, USA
Interests: macrocyclic compounds; strained aromatic systems; carbon nanotubes (CNTs); total synthesis; streamlined chemical synthesis; gene silencing therapeutics; antisense technology
Dr. Simon Giroux

E-Mail Website
Assistant Guest Editor
Vertex Pharmaceuticals, Inc., Boston, MA, USA
Interests: medicinal chemistry; organic chemistry

Special Issue Information

Dear Colleagues,

The master of design who has taught our community about the importance of visual perception, right brain–left brain communication, and component-oriented conception, Professor Stephen Hanessian has illuminated pathways for simplifying structural and stereochemical complexity within the mind's eye by providing pedagogical enlightenment and practical instruction for designing synthetic strategies towards complex natural products and prototypical architectures within bioactive molecules of medicinal interest. Over a career spanning five decades, and still actively pursuing cutting-edge science, Dr. Hanessian has pioneered contributions of significant impact in a broad cross-section of research areas: total synthesis of natural products, medicinal and bio-organic chemistry, asymmetric processes and catalysis, organic methods, carbohydrates, amino acids and their mimetics, supramolecular assemblies, and computer-assisted design. Paying tribute to a devoted academic mentor, whose valuable training of hundreds of students and post-doctoral associates has helped to launch many stellar careers in academia, big pharma, and the biotech industry, this Special Issue of Molecules is dedicated to Dr. Hanessian, the consummate molecular artist, in recognition of original achievements, exemplary scholarly contributions, and prevailing pursuit of excellence in fields of interest to practicing organic and medicinal chemists.

Prof. Dr. William D. Lubell
Prof. Dr. Bradley L. Merner
Dr. Simon Giroux
Guest Editors

Manuscript Submission Information

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Keywords

  • Total synthesis
  • Natural products
  • Medicinal chemistry
  • Computer-assisted synthetic planning
  • Asymmetric processes
  • Supramolecular self-assembly
  • Molecular recognition
  • Carbohydrates
  • Amino acids
  • Mimetics

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Published Papers (9 papers)

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Research

18 pages, 4471 KiB  
Article
Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity
by Mikhail V. Kalyaev, Dmitry S. Ryabukhin, Marina A. Borisova, Alexander Yu. Ivanov, Irina A. Boyarskaya, Kristina E. Borovkova, Lia R. Nikiforova, Julia V. Salmova, Nikolay V. Ul’yanovskii, Dmitry S. Kosyakov and Aleksander V. Vasilyev
Molecules 2022, 27(14), 4612; https://doi.org/10.3390/molecules27144612 - 19 Jul 2022
Cited by 5 | Viewed by 2853
Abstract
Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should [...] Read more.
Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon–carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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17 pages, 3735 KiB  
Article
Conversion of Natural Narciclasine to Its C-1 and C-6 Derivatives and Their Antitumor Activity Evaluation: Some Unusual Chemistry of Narciclasine
by Juana Goulart Stollmaier, Jared Thomson, Mary Ann Endoma-Arias, Razvan Simionescu, Alexandra Vernaza, Nakya Mesa-Diaz, Mitchell Smith, Liqin Du, Alexander Kornienko and Tomas Hudlicky
Molecules 2022, 27(13), 4141; https://doi.org/10.3390/molecules27134141 - 28 Jun 2022
Cited by 3 | Viewed by 1906
Abstract
During the search for a general, efficient route toward the synthesis of C-1 analogues of narciclasine, natural narciclasine was protected and converted to its C-1 enol derivative using a novel semi-synthetic route. Attempted conversion of this material to its triflate in order to [...] Read more.
During the search for a general, efficient route toward the synthesis of C-1 analogues of narciclasine, natural narciclasine was protected and converted to its C-1 enol derivative using a novel semi-synthetic route. Attempted conversion of this material to its triflate in order to conduct cross-coupling at C-1 resulted in a triflate at C-6 that was successfully coupled with several functionalities. Four novel compounds were fully deprotected after seven steps and subjected to evaluation for cytotoxic activity against three cancer cell lines. Only one derivative showed moderate activity compared to that of narciclasine. Spectral and physical data are provided for all new compounds. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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8 pages, 3510 KiB  
Communication
Heteroleptic Copper(I)-Based Complexes Incorporating BINAP and π-Extended Diimines: Synthesis, Catalysis and Biological Applications
by Corentin Cruché, Sayak Gupta, Jeremy Kodanko and Shawn K. Collins
Molecules 2022, 27(12), 3745; https://doi.org/10.3390/molecules27123745 - 10 Jun 2022
Cited by 3 | Viewed by 2402
Abstract
A series of copper-based photocatalysts of the type Cu(NN)(BINAP)BF4 were synthesized bearing π-extended diimine ligands. Their behavior in several photocatalytic processes were evaluated and revealed acceptable levels of activity in an SET process, but negligible activity in PCET [...] Read more.
A series of copper-based photocatalysts of the type Cu(NN)(BINAP)BF4 were synthesized bearing π-extended diimine ligands. Their behavior in several photocatalytic processes were evaluated and revealed acceptable levels of activity in an SET process, but negligible activity in PCET or ET processes. Suitable activity in ET processes could be restored through modification of the ligand. The BINAP-derived complexes were then evaluated for activity against triple-negative breast cancer cell lines. Controls indicated that copper complexes, and not their ligands, were responsible for activity. Encouraging activity was displayed by a homoleptic complex Cu(dppz)2BF4. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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20 pages, 68599 KiB  
Article
Synthesis and Structural Characterization of Pyridine-2,6-dicarboxamide and Furan-2,5-dicarboxamide Derivatives
by Anna Puckowska, Magdalena Gawel, Marlena Komorowska, Pawel Drozdzal, Aleksandra Arning, Damian Pawelski, Krzysztof Brzezinski and Marta E. Plonska-Brzezinska
Molecules 2022, 27(6), 1819; https://doi.org/10.3390/molecules27061819 - 10 Mar 2022
Cited by 4 | Viewed by 2510
Abstract
Derivatives based on pyridine-2-6- and furan-2,5-dicarboxamide scaffolds reveal numerous chemical properties and biological activities. This fact makes them an exciting research topic in supramolecular and coordination chemistry and in discovering new pharmacologically-active compounds. This work aimed to obtain a series of symmetrical pyridine-2-6- [...] Read more.
Derivatives based on pyridine-2-6- and furan-2,5-dicarboxamide scaffolds reveal numerous chemical properties and biological activities. This fact makes them an exciting research topic in supramolecular and coordination chemistry and in discovering new pharmacologically-active compounds. This work aimed to obtain a series of symmetrical pyridine-2-6- and furan-2,5-dicarboxamides through a condensation reaction of the appropriate acyl chlorides and aromatic amides. Successful syntheses were confirmed with NMR spectroscopy. We solved their crystal structures for seven compounds; two pyridine and five furan derivatives. Based on our crystallographic studies, we were able to indicate supramolecular features of the crystals under investigation. Additionally, Hirshfeld surface analysis allowed us to calculate a distribution of intermolecular contacts in the dicarboxamide crystals. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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25 pages, 5004 KiB  
Article
Nucleotide Analogues Bearing a C2′ or C3′-Stereogenic All-Carbon Quaternary Center as SARS-CoV-2 RdRp Inhibitors
by Amarender Manchoju, Renaud Zelli, Gang Wang, Carla Eymard, Adrian Oo, Mona Nemer, Michel Prévost, Baek Kim and Yvan Guindon
Molecules 2022, 27(2), 564; https://doi.org/10.3390/molecules27020564 - 17 Jan 2022
Cited by 5 | Viewed by 2941
Abstract
The design of novel nucleoside triphosphate (NTP) analogues bearing an all-carbon quaternary center at C2′ or C3′ is described. The construction of this all-carbon stereogenic center involves the use of an intramoleculer photoredox-catalyzed reaction. The nucleoside analogues (NA) hydroxyl functional group at C2′ [...] Read more.
The design of novel nucleoside triphosphate (NTP) analogues bearing an all-carbon quaternary center at C2′ or C3′ is described. The construction of this all-carbon stereogenic center involves the use of an intramoleculer photoredox-catalyzed reaction. The nucleoside analogues (NA) hydroxyl functional group at C2′ was generated by diastereoselective epoxidation. In addition, highly enantioselective and diastereoselective Mukaiyama aldol reactions, diastereoselective N-glycosylations and regioselective triphosphorylation reactions were employed to synthesize the novel NTPs. Two of these compounds are inhibitors of the RNA-dependent RNA polymerase (RdRp) of SARS-CoV-2, the causal virus of COVID-19. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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17 pages, 3546 KiB  
Article
Constrained Dipeptide Surrogates: 5- and 7-Hydroxy Indolizidin-2-one Amino Acid Synthesis from Iodolactonization of Dehydro-2,8-diamino Azelates
by Ramakotaiah Mulamreddy and William D. Lubell
Molecules 2022, 27(1), 67; https://doi.org/10.3390/molecules27010067 - 23 Dec 2021
Cited by 1 | Viewed by 2931
Abstract
The constrained dipeptide surrogates 5- and 7-hydroxy indolizidin-2-one N-(Boc)amino acids have been synthesized from L-serine as a chiral educt. A linear precursor ∆4-unsaturated (2S,8S)-2,8-bis[N-(Boc)amino]azelic acid was prepared in five steps from L-serine. Although epoxidation [...] Read more.
The constrained dipeptide surrogates 5- and 7-hydroxy indolizidin-2-one N-(Boc)amino acids have been synthesized from L-serine as a chiral educt. A linear precursor ∆4-unsaturated (2S,8S)-2,8-bis[N-(Boc)amino]azelic acid was prepared in five steps from L-serine. Although epoxidation and dihydroxylation pathways gave mixtures of hydroxy indolizidin-2-one diastereomers, iodolactonization of the ∆4-azelate stereoselectively delivered a lactone iodide from which separable (5S)- and (7S)-hydroxy indolizidin-2-one N-(Boc)amino esters were synthesized by sequences featuring intramolecular iodide displacement and lactam formation. X-ray analysis of the (7S)-hydroxy indolizidin-2-one N-(Boc)amino ester indicated that the backbone dihedral angles embedded in the bicyclic ring system resembled those of the central residues of an ideal type II’ β-turn indicating the potential for peptide mimicry. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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24 pages, 7362 KiB  
Communication
Nickel-Catalyzed Kumada Cross-Coupling Reactions of Benzylic Sulfonamides
by Kirsten A. Hewitt, Claire A. Herbert, Alissa C. Matus and Elizabeth R. Jarvo
Molecules 2021, 26(19), 5947; https://doi.org/10.3390/molecules26195947 - 30 Sep 2021
Cited by 1 | Viewed by 3876
Abstract
Herein, we report a Kumada cross-coupling reaction of benzylic sulfonamides. The scope of the transformation includes acyclic and cyclic sulfonamide precursors that cleanly produce highly substituted acyclic fragments. Preliminary data are consistent with a stereospecific mechanism that allows for a diastereoselective reaction. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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23 pages, 9143 KiB  
Article
Influence of N-Methylation and Conformation on Almiramide Anti-Leishmanial Activity
by Anh Minh Thao Nguyen, Skye Brettell, Noélie Douanne, Claudia Duquette, Audrey Corbeil, Emanuella F. Fajardo, Martin Olivier, Christopher Fernandez-Prada and William D. Lubell
Molecules 2021, 26(12), 3606; https://doi.org/10.3390/molecules26123606 - 12 Jun 2021
Cited by 4 | Viewed by 3443
Abstract
The almiramide N-methylated lipopeptides exhibit promising activity against trypanosomatid parasites. A structure–activity relationship study has been performed to examine the influences of N-methylation and conformation on activity against various strains of leishmaniasis protozoan and on cytotoxicity. The synthesis and biological analysis [...] Read more.
The almiramide N-methylated lipopeptides exhibit promising activity against trypanosomatid parasites. A structure–activity relationship study has been performed to examine the influences of N-methylation and conformation on activity against various strains of leishmaniasis protozoan and on cytotoxicity. The synthesis and biological analysis of twenty-five analogs demonstrated that derivatives with a single methyl group on either the first or fifth residue amide nitrogen exhibited greater activity than the permethylated peptides and relatively high potency against resistant strains. Replacement of amino amide residues in the peptide, by turn inducing α amino γ lactam (Agl) and N-aminoimidazalone (Nai) counterparts, reduced typically anti-parasitic activity; however, peptide amides possessing Agl residues at the second residue retained significant potency in the unmethylated and permethylated series. Systematic study of the effects of methylation and turn geometry on anti-parasitic activity indicated the relevance of an extended conformer about the central residues, and conformational mobility by tertiary amide isomerization and turn geometry at the extremities of the active peptides. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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12 pages, 1874 KiB  
Article
Synthesis of Galectin Inhibitors by Regioselective 3′-O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis
by Karima Belkhadem, Yihong Cao and René Roy
Molecules 2021, 26(1), 115; https://doi.org/10.3390/molecules26010115 - 29 Dec 2020
Cited by 4 | Viewed by 2424
Abstract
Vanillin-based lactoside derivatives were synthetized using phase-transfer catalyzed reactions from per-O-acetylated lactosyl bromide. The aldehyde group of the vanillin moiety was then modified to generate a series of related analogs having variable functionalities in the para- position of the aromatic residue. [...] Read more.
Vanillin-based lactoside derivatives were synthetized using phase-transfer catalyzed reactions from per-O-acetylated lactosyl bromide. The aldehyde group of the vanillin moiety was then modified to generate a series of related analogs having variable functionalities in the para- position of the aromatic residue. The corresponding unprotected lactosides, obtained by Zemplén transesterification, were regioselectively 3′-O-sulfated using tin chemistry activation followed by treatment with sulfur trioxide-trimethylamine complex (Men3N-SO3). Additional derivatives were also prepared from the vanillin’s aldehyde using a Knoevenagel reaction to provide extended α, β-unsaturated carboxylic acid which was next reduced to the saturated counterpart. Full article
(This article belongs to the Special Issue A Tribute to Design and Strategy in Organic Synthesis in Honour of Stephen Hanessian)
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