Recent advances in synthesis and medicinal chemistry of benzodiazepines

被引:69
作者
Arora, Nidhi [1 ]
Dhiman, Prashant [1 ]
Kumar, Shubham [1 ]
Singh, Gurpreet [1 ]
Monga, Vikramdeep [1 ]
机构
[1] ISF Coll Pharm, Dept Pharmaceut Chem, GT Rd, Moga 142001, Punjab, India
关键词
Benzodiazepines; Antimicrobial; Anticancer; Biological activity; SAR; Docking; IN-VITRO CYTOTOXICITY; ONE-POT SYNTHESIS; 1,5-BENZODIAZEPINE DERIVATIVES; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; ENVIRONMENTALLY BENIGN; O-PHENYLENEDIAMINE; PROMOTED SYNTHESIS; DESIGN; ANTICANCER;
D O I
10.1016/j.bioorg.2020.103668
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Benzodiazepines (BZDs) represent a diverse class of bicyclic heterocyclic molecules. In the last few years, benzodiazepines have emerged as potential therapeutic agents. As a result, several mild, efficient and high yielding protocols have been developed that offer access to various functionalized benzodiazepines (BZDs). They are known to possess a wide array of biological activities such as anxiolytic, anticancer, anticonvulsant, antipsychotics, muscle relaxant, anti-tuberculosis, and antimicrobial activities. The fascinating spectrum of biological activities exhibited by BZDs in various fields has prompted the medicinal chemist to design and discover novel benzodiazepine-based analogs as potential therapeutic candidates with the desired biological profile. In this review, an attempt has been made by to summarize (1) Recent advances in the synthetic chemistry of benzodiazepines which enable their synthesis with desired substitution pattern; (2) Medicinal chemistry of BZDs as therapeutic candidates with promising biological profile including insight of mechanistic studies; (3) The correlation of biological data with the structure i.e. structure-activity relationship studies were also included to provide an insight into the rational design of more active agents.
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共 120 条
[1]   Design and synthesis of (3,5-disubstituted isoxazole)-linked [1,5]-benzodiazepine conjugates: evaluation of their antimicrobial and anti-tyrosinase activities [J].
Abdallah, Wejdane ;
Daami-Remadi, Mejda ;
Znati, Mansour ;
Ben Jannet, Hichem ;
Gharbi, Rafik .
JOURNAL OF CHEMICAL RESEARCH, 2017, (01) :12-17
[2]   REACTION OF PYRIDINE 1-OXIDES WITH BENZYNE - BETA-HYDROXYARYLATION OF PYRIDINES VIA [SIGMA2S + PI2A + PI4S] REARRANGEMENTS [J].
ABRAMOVI.RA ;
SHINKAI, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (16) :5265-5267
[3]   A NEW ROUTE TO 1H-1,5-BENZODIAZEPINONES [J].
ACKROYD, J ;
SCHEINMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (07) :339-340
[4]   Novel family of fused tricyclic [1,4]diazepines: Design, synthesis, crystal structures and molecular docking studies [J].
Adamski, Ariel ;
Kruszka, Dariusz ;
Dutkiewicz, Zbigniew ;
Kubicki, Maciej ;
Gorczynski, Adam ;
Patroniak, Violetta .
TETRAHEDRON, 2017, 73 (24) :3377-3386
[5]   Efficient Synthesis and Biological Evaluation of a Novel Series of 1,5-Benzodiazepine Derivatives as Potential Antimicrobial Agents [J].
An, Ying-shuang ;
Hao, Zhen-fang ;
Zhang, Xiu-jun ;
Wang, Lan-zhi .
CHEMICAL BIOLOGY & DRUG DESIGN, 2016, 88 (01) :110-121
[6]   Facile synthesis of 1,4-benzodiazepine-2,5-diones and quinazolinones from amino acids as anti-tubercular agents [J].
Anil, Seegehalli M. ;
Shobith, Rangappa ;
Kiran, Kuppalli. R. ;
Swaroop, Toreshettahally R. ;
Mallesha, Ningegowda ;
Sadashiva, Maralinganadoddi P. .
NEW JOURNAL OF CHEMISTRY, 2019, 43 (01) :182-187
[7]   Synthesis and biological activity of fused tetracyclic Pyrrolo[2,1-c][1,4] benzodiazepines [J].
Annor-Gyamfi, Joel K. ;
Jarrett, John M. ;
Osazee, Joseph O. ;
Bialonska, Dobrusia ;
Whitted, Crystal ;
Palau, Victoria E. ;
Shilabin, Abbas G. .
HELIYON, 2018, 4 (02)
[8]   A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface [J].
Balakrishna, MS ;
Kaboudin, B .
TETRAHEDRON LETTERS, 2001, 42 (06) :1127-1129
[9]   Silica supported fluoroboric acid as a novel, efficient and reusable catalyst for the synthesis of 1,5-benzodiazepines under solvent-free conditions [J].
Bandgar, B. P. ;
Patil, Abasaheb V. ;
Chavan, O. S. .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 256 (1-2) :99-105
[10]   Efficacy of antidepressants and benzodiazepines in minor depression: systematic review and meta-analysis [J].
Barbui, Corrado ;
Cipriani, Andrea ;
Patel, Vikram ;
Ayuso-Mateos, Jose L. ;
van Ommeren, Mark .
BRITISH JOURNAL OF PSYCHIATRY, 2011, 198 (01) :11-16