A Study on Biologically Active Chalcone Based Benzodiazepines
DOI:
https://doi.org/10.51611/iars.irj.v12i02.2022.216Keywords:
Benzodiazepines, Chalcones, Heterocycles, PharmaceuticalsAbstract
Heterocycles that include nitrogen are now indispensable to humanity. The majority of the major pharmaceuticals on the market are composed of heterocycles that include nitrogen. One such substance is benzodiazepine, which was shown to have potential as an anti-anxiety medication in 1955. A novel class of chalcone-based benzodiazepines continues to receive the most attention because of their enhanced pharmacological, medicinal, and biological actions. The present study covers the chemistry of some important biologically active chalcone-based benzodiazepines.
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Archer G. A, Sternbach, L. H. Chem. Rev. 1968, 68, 6, 747-784. DOI: https://doi.org/10.1021/cr60256a004
Mehdi T, Benzodiazepines Revisited. BJMP. 2012; 5(1):a501
Wick JY, The History of Benzodiazepines. The consultant pharmacist. 2013; 28(9):538-548 DOI: https://doi.org/10.4140/TCP.n.2013.538
Tardibono, L. P.; Miller, Synthesis and Anticancer Activity of New Hydroxamic Acid Containing 1,4-Benzodiazepines. M. J. Org. Lett. 2009;11(4):1575-1578 DOI: https://doi.org/10.1021/ol900210h
Chen Y, Le V, Xu, X, Shao X, Liu J, Li Z. Discovery of novel 1,5-benzodiazepine-2,4-dione derivatives as potential anticancer agents. Bioorg. Med. Chem. Lett. 2014; 24(16): 3948- 3951. DOI: https://doi.org/10.1016/j.bmcl.2014.06.041
Misra A, Sharma S, Sharma D, Dubey S, Mishra A, Kishore D, Dwivedi J. Synthesis and molecular docking of pyrimidine incorporated novel analogue of 1,5-benzodiazepine as antibacterial agent. J. Chem. Sci. 2018;130(1):1-12. DOI: https://doi.org/10.1007/s12039-018-1430-7
Kumar R, Joshi YC. Synthesis and antimicrobial, antifungal and anthelmintic activities of 3H-1,5-benzodiazepine derivatives. J. Serb. Chem. Soc. 2008; 73(10): 937-943. DOI: https://doi.org/10.2298/JSC0810937K
Torres S. R, Frode T. S, Nardi, G.M, Vita N, Reeb R, Ferrara P, Ribeiro-do-Valle R. M, Farges R. C. Anti-inflammatory effects of peripheral benzodiazepine receptor ligands in two mouse models of inflammation. Eur. J. Pharmacol. 2000; 408 (2):199-211. DOI: https://doi.org/10.1016/S0014-2999(00)00760-3
Torres S. R. R, Nardi G. M, Ferrara, P, Ribeiro-do-Valle R. M, Farges R. C. Potential role of peripheral benzodiazepine receptors in inflammatory response Eur. J. Pharmacol. 1999; 385: R1- R2. DOI: https://doi.org/10.1016/S0014-2999(99)00745-1
Kamal A, Reddy K. L, Devaiah V, Shankaraiah N, Reddy G. S. K, Raghavan S. Solid-Phase Synthesis of a Library of Pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones with Potential Antitubercular Activity J. Comb. Chem 2007; 9(1): 29-42. DOI: https://doi.org/10.1021/cc0501458
De Sarro G, Ferreri G, Gareri, P.; Russo, E.; De Sarro, A.; Gitto, R.; Chimirri, A. Comparative anticonvulsant activity of some 2,3-benzodiazepine derivatives in rodents. Pharmacol. Biochem. Behav. 2003; 74 (3): 595-602. DOI: https://doi.org/10.1016/S0091-3057(02)01040-7
Grasso S, De Sarro G, De Sarro A, Micale N, Zappala M, Puia G, Baraldi M, De Micheli C. Synthesis and Anticonvulsant Activity of Novel and Potent 2,3-Benzodiazepine AMPA/Kainate Receptor Antagonists. J. Med. Chem. 1999; 42 (21): 4414-4421. DOI: https://doi.org/10.1021/jm991086d
Rathore M. M, Rajput P. R, Parhate V. V Synthesis and Antimicrobial Activity of Some Chalcones and Flavones. Int. J. Chem. Phys. Sci. 2015; 4: 473-477.
Lin Y. M, Zhou Y, Flavin M. T, Zhou L. M, Nie W, Chen F. C. Chalcones and Flavonoids as Anti-Tuberculosis Agents. Bioorganic Med. Chem. 2002; 10 (8): 2795-2802. DOI: https://doi.org/10.1016/S0968-0896(02)00094-9
Alarcón J, Alderete J, Escobar C, Araya R, Cespedes C. L. Aspergillus niger catalyzes the synthesis of flavonoids from chalcones. Biocatal. Biotransformation 2013; 31 (4): 160-167. DOI: https://doi.org/10.3109/10242422.2013.813489
Balasubramanian S, Nair M. G. An Efficient “One Pot” Synthesis of Isoflavones. Synth. Commun. 2000; 30 (3): 469-484. DOI: https://doi.org/10.1080/00397910008087343
Li Y, Sun B, Zhai J, Fu L, Zhang S, Zhang J, Liu H, Xie W, Deng H, Chen Z, Sang F. Synthesis and antibacterial activity of four natural chalcones and their derivatives Tetrahedron Lett. 2019; 60 (43): 151165-151167. DOI: https://doi.org/10.1016/j.tetlet.2019.151165
Arty I. S, Timmerman H, Samhoedi M, Sastrohamidjojo, Sugiyanto, Van Der Goot H. Synthesis of benzylideneacetophenones and their inhibition of lipid peroxidation. Eur. J. Med. Chem. 2000; 35( 4): 449-457. DOI: https://doi.org/10.1016/S0223-5234(00)00137-9
Singh A, Viljoen A, Kremer L, Kumar V. Synthesis and Antimycobacterial Evaluation of Piperazyl-alkyl-Ether Linked 7-Chloroquinoline-Chalcone/Ferrocenyl Chalcone Conjugates .Chemistry Select. 2018; 3 (29): 8511-8513. DOI: https://doi.org/10.1002/slct.201801453
Shibata S. Anti-tumorigenic Chalcones. Stem Cells 1994; 12 (1): 44-52. DOI: https://doi.org/10.1002/stem.5530120109
Go M, Wu X, Liu X. Chalcones: An Update on Cytotoxic and Chemoprotective Properties. Curr. Med. Chem. 2005; 12 (4): 483-499. DOI: https://doi.org/10.2174/0929867053363153
Orlov V.D, Kolos, N. N, Yaremenko F. G, Lavrushin V. F. New aspects of the chemistry of 2,3-dihydro-ih-i,5- benzodiazepine. Chem. Heterocycl. Compd. 1980; 16 (5): 547-550. DOI: https://doi.org/10.1007/BF00561358
Farooq S, Ngaini Z. One-Pot and Two-Pot Synthesis of Chalcone based Mono and Bis-Pyrazolines. Tetrahedron Lett. 2020; 61 (4): 151416. DOI: https://doi.org/10.1016/j.tetlet.2019.151416
Joshi V. D, Kshirsagar M. D, Singhal S. Synthesis and Antimicrobial activities of Various Pyrazolines from Chalcones. Int. J. ChemTech Res. 2012; 4(3): 971-975.
Sunitha V, Kumar A. K, Mahesh M, Shankaraiah P, Jalapathi P, Lincoln C. A. Synthesis and Antimicrobial Evaluation of Bis-3,5-disubstituted Isoxazoles Based Chalcones. Russ. J. Gen. Chem. 2018; 88 (9): 1904-1911. DOI: https://doi.org/10.1134/S1070363218090232
Roy R. S, Chundawat J. S, Dulawat S. S. Microwave assisted synthesis of 2,4-diaryl-2,3- dihydro-1H-1,5-benzodiazepines on solventless inorganic solid support and their antibacterial activities. Afinidad 2008; 65 (537): 404--409.
Bhatia M. S, houdhari P. B, Ingale K. B, Zarekar, B. E. Synthesis, screening and QSAR studies of 2,4-disubstituted 1,5-benzodiazepine derivatives. Orient. J. Chem. 2008; 24 (1): 147-152.
Kamal A, Balakishan G, Ramakrishna G, Basha Shaik T, Sreekanth K, Balakrishna M, Rajender, Dastagiri D, Kalivendi S. V. Synthesis and biological evaluation of cinnamido linked pyrrolo[2,1-c][1,4] benzodiazepines as antimitotic agents. Eur. J. Med. Chem. 2010; 45(9): 3870-3884. DOI: https://doi.org/10.1016/j.ejmech.2010.05.041
Hussain N, Dangi R, Talesara G. L. Synthesis and biological evaluation of some N-ethoxyphthalimido-4-phenyl-6- subsituted phenyl-2,3a,4,5-tetrahydro-3H-indazol-3-one via Robinson annulations reaction. Iran. J. Org. Chem. 2011; 3 (1): 563-572.
Yadav J. S, Srivastava Y. K. Microwave assisted rapid and efficient synthesis, characterization and pharmacological evaluation of some novel benzimidazole assembled 1,5- benzodizepine and 1,5-benzothiazepine derivatives. Der Pharm. Lett. 2011; 3 (2):284-291.
Venkat S. S. V. Synthesis of novel 1,5- Benzodiazepine derivatives as potential antimicrobial agents. Int. Multiling. Res. J. 2014; 1:0113.
Salve P. S, Mali D. S. An expeditious and efficient microwave assisted synthesis of 1,5-benzodiazepine derivatives. J. Chem. Pharm. Res. 2013; 5 (2): 158-161.
Salve P, Mali D. Evaluation of antimicrobial and antifungal activities of some newly synthesized 2,4-disubstituted-1,5- benzodiazepines. J. Cell Tissue Res. 2013; 13(2): 3687-3690.
Baseer M. A, Shaikh S. Synthesis and antimicrobial activities of some new 2, 3-dihydro-1, 5- benzodiazepine derivatives, Int. J. Pharm. Sci. Res. 2013; 4 (7): 2717-2720.
Sharma S, Jain R, Chawla C. Synthesis and Biological Activities of Some Benzodiazepine Derivatives. J. Chem. Pharm. Res. 2013; 5(7): 46-55.
Sharma V. P, Kumar, P. Synthesis, Spectral Studies and Antibacterial Activity of 3-(4-Phenyl-2,3-dihydro-1,5-benzodiazepin-2-yl)chromone. Asian J. Chem. 2014; 26(13): 3992-3994. DOI: https://doi.org/10.14233/ajchem.2014.16377
El-Subbagh H. I, Hassan G. S, El-Messery S. M, Al-Rashood S. T, Al-Omary F. A. M, Abulfadl Y. S, Shabayek M. I. Nonclassical antifolates, part 5. Benzodiazepine analogs as a new class of DHFR inhibitors: Synthesis, antitumor testing and molecular modelling study. Eur. J. Med. Chem. 2014; 74: 234-245. DOI: https://doi.org/10.1016/j.ejmech.2014.01.004
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Copyright (c) 2022 Anirudh Singh, Anjaneyulu Bendi, Aditi Tiwari
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