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Bioactive Heterocyclic Chemistry

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

Deadline for manuscript submissions: closed (31 January 2024) | Viewed by 7100

Special Issue Editors


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Guest Editor
Department of Chemistry, Xi’an Jiaotong Liverpool University, Suzhou 215123, China
Interests: organic synthesis; organocatalysis; bioactive heterocycles; flavonoids; drug delivery systems; small molecular weight enzyme inhibitors

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Guest Editor
Egyptian Petroleum Research Institute, Nasr City, Cairo 11727, Egypt
Interests: organic synthesis; catalysis of organic reactions; cyclization; domino reactions; heterocycles; coumarin; isoxazoles; pyrroles; pyridines; diazo compounds; organophosphorus chemistry; medicinal chemistry; dyes chemistry

Special Issue Information

Dear Colleagues,

Heterocyclic compounds are pervasive in many areas of life sciences and technology and represent an indispensable part of synthetic organic chemistry. More than half of US FDA-approved drugs contain heterocyclic compounds. Thus, numerous frequently applied reactions, such as domino Knoevenagel reaction, Diels–Alder reaction, Hantzsch dihydropyridine synthesis, Wittig reaction, Feist–Bénary furan synthesis, etc., have been recognized as milestones for the synthesis of heterocycles. The development of modern technologies requires new organic compounds with the necessary properties for the creation and introduction of new drugs. We invite researchers to contribute original research papers or reviews to this Special Issue of Molecules which report on bioactive heterocyclic chemistry, especially those possessing useful biologically active properties.

Dr. Magdalini Matziari
Dr. Moaz M. Abdou
Prof. Dr. Naresh Kumar
Guest Editors

Manuscript Submission Information

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Keywords

  • heterocycles
  • organic synthesis
  • catalysis
  • cyclization
  • cycloaddition
  • domino reactions
  • bioactivity

Published Papers (5 papers)

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Research

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11 pages, 2766 KiB  
Article
Rhodium-Catalyzed Tandem Asymmetric Allylic Decarboxylative Addition and Cyclization of Vinylethylene Carbonates with N-Nosylimines
by Xiao-Lin Wang, Hai-Bin Jiang, Sheng-Cai Zheng and Xiao-Ming Zhao
Molecules 2024, 29(5), 1019; https://doi.org/10.3390/molecules29051019 - 26 Feb 2024
Viewed by 588
Abstract
A enantioselective tandem transformation, concerning asymmetric allylic decarboxylative addition and cyclization of N-nosylimines with vinylethylene carbonates (VECs), in the presence of [Rh(C2H4)2Cl]2, chiral sulfoxide-N-olefin tridentate ligand has been developed. The reaction of [...] Read more.
A enantioselective tandem transformation, concerning asymmetric allylic decarboxylative addition and cyclization of N-nosylimines with vinylethylene carbonates (VECs), in the presence of [Rh(C2H4)2Cl]2, chiral sulfoxide-N-olefin tridentate ligand has been developed. The reaction of VECs with various substituted N-nosylimines proceeded smoothly under mild conditions, providing highly functionalized oxazolidine frameworks in good to high yields with good to excellent enantioselectivity. Full article
(This article belongs to the Special Issue Bioactive Heterocyclic Chemistry)
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14 pages, 2363 KiB  
Article
DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups
by Yong-Jun Zhou, Yong-Gan Fang, Kai Yang, Jian-Yun Lin, Huan-Qing Li, Zu-Jia Chen and Zhao-Yang Wang
Molecules 2023, 28(15), 5635; https://doi.org/10.3390/molecules28155635 - 25 Jul 2023
Cited by 3 | Viewed by 951
Abstract
Organic thioethers play an important role in the discovery of drugs and natural products. However, the green synthesis of organic sulfide compounds remains a challenging task. The convenient and efficient synthesis of 5-alkoxy-3-halo-4-methylthio-2(5H)-furanones from DMSO is performed via the mediation of [...] Read more.
Organic thioethers play an important role in the discovery of drugs and natural products. However, the green synthesis of organic sulfide compounds remains a challenging task. The convenient and efficient synthesis of 5-alkoxy-3-halo-4-methylthio-2(5H)-furanones from DMSO is performed via the mediation of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), affording a facile route for the sulfur-functionalization of 3,4-dihalo-2(5H)-furanones under transition metal-free conditions. This new approach has demonstrated the functionalization of non-aromatic Csp2-X-type halides with unique structures containing C-X, C-O, C=O and C=C bonds. Compared with traditional synthesis methods using transition metal catalysts with ligands, this reaction has many advantages, such as the lower temperature, the shorter reaction time, the wide substrate range and good functional group tolerance. Notably, DMSO plays multiple roles, and is simultaneously used as an odorless methylthiolating reagent and safe solvent. Full article
(This article belongs to the Special Issue Bioactive Heterocyclic Chemistry)
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14 pages, 2087 KiB  
Article
Diastereoselective Formal 1,3-Dipolar Cycloaddition of Trifluoroethyl Amine-Derived Ketimines Enables the Desymmetrization of Cyclopentenediones
by Lin-Qiang Li, Jian-Qiang Zhao, Yan-Ping Zhang, Yong You, Zhen-Hua Wang, Zhen-Zhen Ge, Ming-Qiang Zhou and Wei-Cheng Yuan
Molecules 2023, 28(14), 5372; https://doi.org/10.3390/molecules28145372 - 13 Jul 2023
Cited by 3 | Viewed by 974
Abstract
In this research, a metal-free diastereoselective formal 1,3-dipolar cycloaddition of N-2,2,2-trifluoroethylisatin ketimines and cyclopentene-1,3-diones which can efficiently lead to the desymmetrization of cyclopentene-1,3-diones is developed. With the developed protocol, a series of tetracyclic spirooxindoles containing pyrrolidine and cyclopentane subunits can be smoothly [...] Read more.
In this research, a metal-free diastereoselective formal 1,3-dipolar cycloaddition of N-2,2,2-trifluoroethylisatin ketimines and cyclopentene-1,3-diones which can efficiently lead to the desymmetrization of cyclopentene-1,3-diones is developed. With the developed protocol, a series of tetracyclic spirooxindoles containing pyrrolidine and cyclopentane subunits can be smoothly obtained with good results (up to 99% yield and 91:9 dr). Furthermore, the methodology can be extended to trifluoromethyl-substituted iminomalonate, and the corresponding formal [3+2] cycloaddition reaction affords bicyclic heterocycles containing fused pyrrolidine and cyclopentane moieties in moderate yields with >20:1 dr. The synthetic potential of the methodology is demonstrated by the scale-up experiment and by versatile transformations of the products. Full article
(This article belongs to the Special Issue Bioactive Heterocyclic Chemistry)
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19 pages, 6967 KiB  
Article
Design, Synthesis, and Biological Evaluation of Phenyloxadiazole Sulfoxide Derivatives as Potent Pseudomonas aeruginosa Biofilm Inhibitors
by Xinyi Ye, Shen Mao, Yasheng Li, Zhikun Yang, Aoqi Du and Hong Wang
Molecules 2023, 28(9), 3879; https://doi.org/10.3390/molecules28093879 - 4 May 2023
Viewed by 1447
Abstract
With the development of antimicrobial agents, researchers have developed new strategies through key regulatory systems to block the expression of virulence genes without affecting bacterial growth. This strategy can minimize the selective pressure that leads to the emergence of resistance. Quorum sensing (QS) [...] Read more.
With the development of antimicrobial agents, researchers have developed new strategies through key regulatory systems to block the expression of virulence genes without affecting bacterial growth. This strategy can minimize the selective pressure that leads to the emergence of resistance. Quorum sensing (QS) is an intercellular communication system that plays a key role in the regulation of bacterial virulence and biofilm formation. Studies have revealed that the QS system controls 4–6% of the total number of P. aeruginosa genes, and quorum sensing inhibitors (QSIs) could be a promising target for developing new prevention and treatment strategies against P. aeruginosa infection. In this study, four series of phenyloxadiazole and phenyltetrazole sulfoxide derivatives were synthesized and evaluated for their inhibitory effects on P. aeruginosa PAO1 biofilm formation. Our results showed that 5b had biofilm inhibitory activity and reduced the production of QS-regulated virulence factors in P. aeruginosa. In addition, silico molecular docking studies have shown that 5b binds to the P. aeruginosa QS receptor protein LasR through hydrogen bond interaction. Preliminary structure–activity relationship and docking studies show that 5b has broad application prospects as an anti-biofilm compound, and further research will be carried out in the future to solve the problem of microbial resistance. Full article
(This article belongs to the Special Issue Bioactive Heterocyclic Chemistry)
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Review

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50 pages, 10215 KiB  
Review
Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review
by Ramsha Munir, Ameer Fawad Zahoor, Sadia Javed, Bushra Parveen, Asim Mansha, Ahmad Irfan, Samreen Gul Khan, Ali Irfan, Katarzyna Kotwica-Mojzych and Mariusz Mojzych
Molecules 2023, 28(15), 5651; https://doi.org/10.3390/molecules28155651 - 26 Jul 2023
Cited by 2 | Viewed by 2602
Abstract
Simmons–Smith cyclopropanation is a widely used reaction in organic synthesis for stereospecific conversion of alkenes into cyclopropane. The utility of this reaction can be realized by the fact that the cyclopropane motif is a privileged synthetic intermediate and a core structural unit of [...] Read more.
Simmons–Smith cyclopropanation is a widely used reaction in organic synthesis for stereospecific conversion of alkenes into cyclopropane. The utility of this reaction can be realized by the fact that the cyclopropane motif is a privileged synthetic intermediate and a core structural unit of many biologically active natural compounds such as terpenoids, alkaloids, nucleosides, amino acids, fatty acids, polyketides and drugs. The modified form of Simmons–Smith cyclopropanation involves the employment of Et2Zn and CH2I2 (Furukawa reagent) toward the total synthesis of a variety of structurally complex natural products that possess broad range of biological activities including anticancer, antimicrobial and antiviral activities. This review aims to provide an intriguing glimpse of the Furukawa-modified Simmons–Smith cyclopropanation, within the year range of 2005 to 2022. Full article
(This article belongs to the Special Issue Bioactive Heterocyclic Chemistry)
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