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PHARMASPIRE - Volume 13, Issue 4 , October - December, 2021

Pages: 177-181
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Synthesis and antibacterial evaluation of naphthalene based 1,5-benzodiazepine derivatives

Author: Anjali Saini, Vikramdeep Monga, Gurpreet Singh

Category: Pharmaceutics


Various substituted 1,5-benzodiazepines were synthesized by condensing different naphthalene-based chalcones with o-phenylenediamine in methanol using piperidine as a base under refluxing conditions and were obtained in good yield after purification. The final compounds (5a-e) were structurally elucidated and evaluated in vitro for antibacterial activity against three human pathogenic bacterial strains using the disc diffusion method and MIC was determined by serial dilution method. The antibacterial evaluation led to the identification of compounds 5d and 5e as the most potent molecule of the series. The promising compounds identified in the study can be exploited in near future for the design of more potent candidates with better efficacy.

Keywords: 1, 5-Benzodiazepines, antibacterial activity, chalcones, naphthalene


  1. Alan HF, Neil AR, Matthews KR, Waters AP. Drug resistance in eukaryotic microorganisms. Nat Microbiol 2016;1:1-14.
  2. Velez R, Sloand E. Combating antibiotic resistance, mitigating future threats and ongoing initiatives. J Clin Nur 2016;25:1886-9.
  3. Boucher HW, Talbot GH, Bradley JS, Edwards JE, Gilbert D, Rice LB, et al. Bad bugs, no drugs: No ESKAPE? An update from the infectious diseases society of America. Clin Infect Dis 2009;48:1-12.
  4. Singh G, Monga V. Synthesis, structural identification, and biological evaluation of naphthalene-based pyrimidine. Pharmaspire 2019;11:88-92.
  5. McManus MC. Mechanisms of bacterial resistance to antimicrobial agents. J Health Syst Pharm 1999;54:1420-33.
  6. Kong Q, Yang Y. Recent advances in antibacterial agents. Bioorg Med Chem Lett 2021;35:127799.
  7. Vila JO, Moreno-Morales J, Ballesté-Delpierre C. Current landscape in the discovery of novel antibacterial agents. Clin Microbiol Infect 2020;26:596-603.
  8. Fair RJ, Tor Y. Antibiotics and bacterial resistance in the 21st century. Perspect Med Chem 2014;6:25-64.
  9. Sharma M, Chaturvedi V, Manju YK, Bhatnagar S, Srivastava K, Puri SK, et al. Substituted quinolinyl chalcones and quinolinyl pyrimidines as a new class of anti-infective agents. Eur J Med Chem 2009;44:2081-91.
  10. Payne DJ, Gwynn MN, Holmes DJ, Pompliano DL. Drugs for bad bugs: Confronting the challenges of antibacterial discovery. Nat Rev Drug Discov 2007;6:29-40.
  11. Jones P, Mempin M, Hu H, Chowdhury D, Foley M, Cooter R, et al. The functional influence of breast implant outer shell morphology on bacterial attachment and growth. Plast Reconstruct Surg 2018;142:837-49.
  12. Arora N, Dhiman P, Kumar S, Singh G, Monga V. Recent advances in synthesis and medicinal chemistry of benzodiazepines. Bioorg Chem 2020;97:103668.
  13. Kaufmann CN, Spira AP, Depp CA, Mojtabai R. Long-term use of benzodiazepines and nonbenzodiazepine hypnotics, 1999-2014. Psychiatr Serv 2018;69:235-8.
  14. Paton C. Benzodiazepines and disinhibition: A review, Psychiatr Bull 2002;26:460-2.
  15. Batlle E, Lizano E, Viñas M, Pujol MD. 1,4-benzodiazepines and new derivatives: Description, analysis, and organic synthesis. Med Chem 2019;63-90.
  16. Barbui C, Cipriani A, Patel V, Ayuso-Mateos JL, Ommeren MV. Efficacy of antidepressants and benzodiazepines in minor depression: Systematic review and meta-analysis. Br J Psychiatry 2011;198:11-6.
  17. Malik N, Iyamu ID, Scheidt KA, Schiltz GE. Synthesis of a novel fused pyrrolodiazepine-based library with anti-cancer activity. Tetrahedron Lett 2018;59:1513-6.
  18. Nagaraju B, Kovvuri J, Babu KS, Adiyala PR, Nayak VL, Alarifi A. A facile onepot C-C and C-N bond formation for the synthesis of spiro-benzodiazepines and their cytotoxicity. Tetrahedron 2017;73:6969-76.
  19. Kumar CP, Reddy TS, Mainkar PS, Bansal V, Shukla R, Chandrasekhar S. Synthesis and biological evaluation of 5,10-dihydro-11 H-dibenzo[b, e][1,4 diazepine-11-one structural derivatives as anticancer and apoptosis-inducing agents. Eur J Med Chem 2016;108:674-86.
  20. Singh G, Nayak SK, Monga V. Synthesis and biological screening of some new 1,5-benzodiazepine derivatives as promising antibacterial and antitubercular agents. Indian J Heterocyc Chem 2017;27:143-9.