Multicomponent reactions as a potent tool for the synthesis of benzodiazepines

作者: Ahmad Shaabani , Ahmad Shaabani , Siamak Javanbakht , Mohammad Taghi Nazeri , Hassan Farhid

DOI: 10.1039/D0OB02600J

关键词: Biochemical engineeringChemistry

摘要: Benzodiazepines (BZDs), a diverse class of benzofused seven-membered N-heterocycles, display essential pharmacological properties and play vital roles in some biochemical processes. They have mainly been prescribed as potential therapeutic agents, which interestingly represent various biological activities such anticancer, anxiolytic, antipsychotic, anticonvulsant, antituberculosis, muscle relaxant, antimicrobial activities. The extensive BZDs fields encouraged medicinal chemists to discover design novel BZD-based scaffolds candidates with the favorite activity through an efficient protocol. Although certainly valuable important, conventional synthetic routes these bicyclic benzene compounds contain methodologies often requiring multistep procedures, suffer from waste materials generation lack sustainability. By contrast, multicomponent reactions (MCRs) recently advanced green strategy for synthesizing desired scope. In this regard, MCRs, especially Ugi Ugi-type reactions, efficiently conveniently supply complex synthons, can easily be converted via suitable post-transformations. Also, Mannich-type provide speedy economic approaches one-pot one-step synthesis BZDs. As result, functionalized-BZDs achieved by developing mild, efficient, high-yielding MCR protocols. This review covers all aspects particular focus on MCRs well mechanism chemistry present manuscript opens new avenue organic, medicinal, industrial safe, environmentally benign, economical methods known

参考文章(303)
Steven Gunawan, Gary S. Nichol, Shashi Chappeta, Justin Dietrich, Christopher Hulme, Concise Preparation of Novel Tricyclic Chemotypes: Fused Hydantoin-benzodiazepines. Tetrahedron Letters. ,vol. 51, pp. 4689- 4692 ,(2010) , 10.1016/J.TETLET.2010.06.131
Alexander Stadler, Behrooz H Yousefi, Doris Dallinger, Peter Walla, Erik Van der Eycken, Nadya Kaval, C Oliver Kappe, None, Scalability of Microwave-Assisted Organic Synthesis. From Single-Mode to Multimode Parallel Batch Reactors Organic Process Research & Development. ,vol. 7, pp. 707- 716 ,(2003) , 10.1021/OP034075+
Barry B. Touré, Dennis G. Hall, Natural product synthesis using multicomponent reaction strategies. Chemical Reviews. ,vol. 109, pp. 4439- 4486 ,(2009) , 10.1021/CR800296P
Alexander Dömling, The discovery of new isocyanide-based multi-component reactions. Current Opinion in Chemical Biology. ,vol. 4, pp. 318- 323 ,(2000) , 10.1016/S1367-5931(00)00095-8
Wen-Bin Yi, Chun Cai, The synthesis of 1,5-benzodiazepines in a fluorous aqueous emulsion Journal of Fluorine Chemistry. ,vol. 130, pp. 1054- 1058 ,(2009) , 10.1016/J.JFLUCHEM.2009.08.005
Zhigang Xu, Justin Dietrich, Arthur Y. Shaw, Christopher Hulme, Two-step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines Tetrahedron Letters. ,vol. 51, pp. 4566- 4569 ,(2010) , 10.1016/J.TETLET.2010.06.116
Yinbo Chen, Vanminh Le, Xiaoyong Xu, Xusheng Shao, Jianwen Liu, Zhong Li, Discovery of novel 1,5-benzodiazepine-2,4-dione derivatives as potential anticancer agents. Bioorganic & Medicinal Chemistry Letters. ,vol. 24, pp. 3948- 3951 ,(2014) , 10.1016/J.BMCL.2014.06.041
K Barry Sharpless, Roman Manetsch, In situ click chemistry: a powerful means for lead discovery Expert Opinion on Drug Discovery. ,vol. 1, pp. 525- 538 ,(2006) , 10.1517/17460441.1.6.525