Main Article Content

Abstract

8-Substituted-2,5-dihydro-1,5-benzothiazepine derivatives have been synthesized by the reaction of 1-(2-furyl)-3-(3,4-dimethoxyphenyl)-2-propenone with six 5-substiuted-2-aminobenzenethiols in dry ethanol saturated with dry HCl gas and also in the presence of aluminium nitrate as catalyst in dry ethanol. All the newly synthesized compounds were characterized by analytical and spectral data comprising IR, 1H NMR, 13C NMR, 19F NMR and mass studies. All these compounds have also been evaluated for their antimicrobial assay against the Gram-positive bacteria, Staphylococcus aureus and the Gram-negative bacteria, Pseudomonas aeruginosa and the fungus, Candida albicans. The antifungal activity was found to be more significant than antibacterial activity.

Keywords

Aluminium nitrate 1,5-Benzothiazepines 2-Aminobenzenethiol Antimicrobial activity

Article Details

How to Cite
Sharma, P. (2019). Antimicrobial Evaluation and Efficient Green Synthesis of 8-Substituted-2,5-dihydro-1,5-benzothiazepine Derivatives. Asian Journal of Organic & Medicinal Chemistry, 4(1), 32–35. https://doi.org/10.14233/ajomc.2019.AJOMC-P168

References

  1. F.L. Ansari, F. Iftikhar, Ihsan-ul-Haq, B. Mirza, M. Baseer and U. Rashid, Solid-Phase Synthesis and Biological Evaluation of a Parallel Library of 2,3-dihydro-1,5-benzothiazepines, Bioorg. Med. Chem., 16, 7691 (2008); https://doi.org/10.1016/j.bmc.2008.07.009.
  2. G.R. Mhaske, S.S. Bajod, D.M. Ambhore and S.N. Shelke, Synthesis and Evaluation of Novel 1,5-Benzothiazepine Derivatives as Anti-Inflam-matory Agents, Int. J. Innov. Res. Sci. Eng. Technol., 3, 13208 (2014).
  3. K.L. Ameta, N.S. Rathore and B. Kumar, Synthesis and in vitro Anti-Breast Cancer Activity of Some Novel 1,5-Benzothiazepine Derivatives, J. Serb. Chem. Soc., 77, 725 (2012); https://doi.org/10.2298/JSC110715219A.
  4. A.P. Nikalje and D. Vyawahare, Facile Green Synthesis of 2,4-Substi-tuted-2,3-Dihydro-1,5-Benzothiazepine Derivatives as Novel Anti-convulsant and Central Nervous System (CNS) Depressant Agents, African J. Pure Appl. Chem., 5, 422 (2011).
  5. W. Ben-Cherif, R. Gharbi, H. Sebai, D. Dridi, N.A. Boughattas and M. Ben-Attia, Neuropharmacological Screening of Two 1,5-Benzodiazepine Compounds in Mice, C. R. Biol., 333, 214 (2010); https://doi.org/10.1016/j.crvi.2009.09.015.
  6. P. Sharma and S. Pant, Syntheses and Antimicrobial Evaluation of Bicyclic 8-Substituted-2,5-dihydro-2-(3,4-dimethoxyphenyl)-4-(4-methylphenyl)-1,5-benzothiazepines, Int. J. Chem. Sci. Appl., 5, 7 (2014).
  7. S. Pant, P. Sharma, A. Sharma, R. Mishra and U.C. Pant, Syntheses of 1,5-Benzothiazepines: Part XXXIV-Syntheses and Antimicrobial Studies of 8-Substituted-2-(4-methoxyphenyl/3,4-dimethoxyphenyl)-2,5-dihydro-4-(2-thienyl)-1,5-benzothiazepines, J. Indian Chem. Soc., 85, 406 (2008).
  8. S. Pant, P. Sharma, B.S. Sharma and U.C. Pant, Syntheses of 1,5-Benzothiazepines: Part XXXIII- Syntheses and Antimicrobial Studies of 10-Substituted-6-(4-methoxyphenyl)-6H-6a,7-dihydro-7-(4-methoxyphenyl/3,4-dimethoxyphenyl)[1]benzopyrano[3,4-c][1,5]- benzothiazepines, Indian J. Chem., 46B, 1537 (2007).
  9. N. Bhasker, Y. Prashanthi and B V. Subba Reddy, Piperidine Mediated Synthesis of Hetero Chalcones and 8-Substituted-2, 5-dihydro-2-(2-furanyl)-4-(2-thienyl)-1, 5-benzothiazepines as Antibacterial Agents, Chem. Sci. Trans., 3, 11 (2014); https://doi.org/10.7598/cst2014.549.
  10. D.S. Ghotekar, R.S. Joshi, P.G. Mandhane, S.S. Bhagat and C.H. Gill, Synthesis of Some Biologically Important Fluorinated 3-Chloro-chromones and 1,5-Benzothiazepines as Antimicrobial and Antifungal Agents, Indian J. Chem., 49B, 1267 (2010).
  11. K.G. Desai and K.R. Desai, Microwave Enhanced Heterocyclization: A Convenient Procedure for Antimicrobial 1,5-Benzothiazepine Compounds, Indian J. Chem., 46B, 1179 (2007).
  12. N. Garg, T. Chandra, Archana, A.B. Jain and A. Kumar, Synthesis and Evaluation of Some New Substituted Benzothiazepine and Benzoxaze-pine Derivatives as Anticonvulsant Agents, Eur. J. Med. Chem., 45, 1529 (2010); https://doi.org/10.1016/j.ejmech.2010.01.001.
  13. S. Pant, H. Chandra, P. Sharma and U.C. Pant, Syntheses of 1,5-Benzo-thiazepines: Part XXXII-Syntheses of 8-Substituted-2,5-dihydro-2-(4-pyridyl)-4-(2-thienyl)-1,5-benzothiazepines, Indian J. Chem., 45B, 1325 (2006).
  14. S. Pant, P. Sharma and U.C. Pant, Syntheses of 1,5-Benzothiazepines: Part XXXVI- Syntheses and Antimicrobial Studies of 8-substituted-2-(2-chlorophenyl)-2,5-dihydro-4-(4-chlorophenyl/2-thienyl)-1,5-benzo-thiazepines, Phosphorus Sulfur Silicon Rel. Elem., 183, 2974 (2008); https://doi.org/10.1080/10426500802048920.
  15. P. Sharma. Biological Evaluation and Microwave Assisted Synthesis of 1,5-Benzothiazepine, Int. J. Appl. Eng. Res., 10, 27467 (2015).
  16. A.V. Chate, R.S. Joshi, P.G. Mandhane and C.H. Gill, An Improved Procedure for the Synthesis of 1,5-Benzothiazepines using Ceric Amm-onium Nitrate, J. Korean Chem. Soc., 55, 776 (2011); https://doi.org/10.5012/jkcs.2011.55.5.776.
  17. A.J. Khan, M.Z. Ahmed and M.A. Basser, Aluminium Nitrate-Catalyzed Multi Component, One-Pot Synthesis of 1,5-Benzothiazepines under Mild Conditions, Int. J. Chem. Stud., 1, 153 (2013).
  18. A. Bauer, W.M.M. Kirby, J. Sherris and M. Turck, Antibiotic Suscep-tibility Testing by a Standardized Single Disk Method, Am. J. Clin. Pathol., 45, 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493.