Main Article Content

Abstract

A new organic compound, N-[4-(1,3-benzothiazol-2-ylcarbamoyl)-phenyl]pyrazine-2-carboxamide was synthesized through the reaction between 4-amino-N-(benzo[d]thiazol-2-yl)benzamide and pyrazine-2-carboxylic acid. The synthesized compound has been characterized by spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR and mass spectroscopy. The synthesized compound was screened to antibacterial (Staphylococcus aureus, Klebsiella pneumonia and Escherichia coli), antifungal (Candida albicans and Aspergillus niger) activities. The anticancer activity of the title compound was also evaluated against MDA-MB-231 breast cancer cells.

Keywords

Benzothiazole Quinoline Carboxamide Antibacterial activity Antifungal activity Anticancer activity.

Article Details

How to Cite
Senthilkumar, G., Umarani, C., & Satheesh, D. (2021). Synthesis, Spectral Characterization, Antibacterial, Antifungal and Anticancer Evaluation of N-[4-(1,3-Benzothiazol-2-ylcarbamoyl)phenyl]pyrazine-2-carboxamide. Asian Journal of Organic & Medicinal Chemistry, 6(2), 102–106. https://doi.org/10.14233/ajomc.2021.AJOMC-P320

References

  1. R. Zhang, S. Jin, Y. Wan, S. Lin and Z. Yan, HBr/H2O2-Mediated Formation of C–S Bond with Thiosulfates, Tetrahedron Lett., 59, 841 (2018); https://doi.org/10.1016/j.tetlet.2018.01.055
  2. P. Tehri, B. Aegurula and R.K. Peddinti, Iodine-Catalyzed Regio-selective Synthesis of b-Hydroxysulfides, Tetrahedron Lett., 58, 2062 (2017); https://doi.org/10.1016/j.tetlet.2017.04.043
  3. N. Azizi and M. Edrisi, Biodegradable Choline Hydroxide Promoted Environmentally Benign Thiolysis of Epoxides, Tetrahedron Lett., 57, 525 (2016); https://doi.org/10.1016/j.tetlet.2015.12.080
  4. M.-Y. Chang, Y.-H. Huang and H.-S. Wang, Synthesis of 1,1-Diaryl-ethylenes, Tetrahedron, 72, 3022 (2016); https://doi.org/10.1016/j.tet.2016.04.018
  5. S.R. Lanke and B.M. Bhanage, Amberlyst-15©: An Efficient Heterogeneous Reusable Catalyst for Selective Anti-Markovnikov Addition of Thiols to Alkenes/Alkynes and for Thiolysis of Epoxides, Catal. Commun., 41, 29 (2013); https://doi.org/10.1016/j.catcom.2013.06.032
  6. T. Sato, Y. Okumura, J. Itai and T. Fujisawa, (S)-b,w-Dihydroxyalkyl Phenyl Sulfones. Synthesis by Bakers Yeast Reduction and Use as Precursors of Optically Active Lactones, Chem. Lett., 17, 1537 (1988); https://doi.org/10.1246/cl.1988.1537
  7. R. Tanikaga, K. Hosoya and A. Kaji, Synthesis of Enantiomerically Pure 2,5-Disubstituted Tetrahydrofurans using Readily Prepared (2S)-1-phenylsulphonylalkan-2-ols, J. Chem. Soc. Perkin Trans. I, 1799 (1987); https://doi.org/10.1039/p19870001799
  8. J. Otera, H. Misawa and K. Sugimoto, Mechanistic Aspects and Profiles of the Double Elimination Reaction of b-Substituted Sulfones, J. Org. Chem., 51, 3830 (1986); https://doi.org/10.1021/jo00370a016
  9. A. El-Awa, M.N. Noshi, X.M. Du Jourdin and P.L. Fuchs, Chem. Rev., 109, 2315 (2009); https://doi.org/10.1021/cr800309r
  10. A. York, Rewiring Cellular Dynamics and Metabolism, Nat. Rev. Microbiol., 15, 576 (2017); https://doi.org/10.1038/nrmicro.2017.114
  11. N.C. Desai, D. Pandya and D. Vaja, Synthesis and Antimicrobial Activity of Some Heterocyclic Compounds bearing Benzimidazole and Pyrazoline Motifs, Med. Chem. Res., 27, 52 (2018); https://doi.org/10.1007/s00044-017-2040-5
  12. U.N. Sekar, B.B.N. Padalkar, V.D. Gupta, K.R. Pharangare, V.S. Patil and P.G. Umape, Oxidation of Thioacids by Quinaldinium Fluoro-chromate, Arab. J. Chem., 9, S1125 (2016); https://doi.org/10.1016/j.arabjc.2013.11.022
  13. Q.A. Mckellar and E.W. Scott, The Benzimidazole Anthelmintic Agents-A Review, J. Vet. Pharmacol. Ther., 13, 223 (1990); https://doi.org/10.1111/j.1365-2885.1990.tb00773.x
  14. L. Garuti, M. Roberti, M. Malagoli, T. Rossi and M. Castelli, Synthesis and Antiproliferative Activity of Some Benzimidazole-4,7-dione Derivatives, Bioorg. Med. Chem. Lett., 10, 2193 (2000); https://doi.org/10.1016/S0960-894X(00)00429-7
  15. S.I. Alaqeel, Synthetic Approaches to Benzimidazoles from o-Phenyl-enediamine: A Literature Review, J. Saudi Chem. Soc., 21, 229 (2017); https://doi.org/10.1016/j.jscs.2016.08.001
  16. A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Antibiotic Susceptibility Testing by a Standardized Single Disk Method, J. Am. Clin. Pathol., 45(4_ts), 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
  17. C. Perez and C. Anesini, in vitro Antibacterial Activity of Argentine Folk Medicinal Plants against Salmonella typhi, J. Ethnopharmacol., 44, 41 (1994); https://doi.org/10.1016/0378-8741(94)90097-3