Synthesis and antimicrobial activity of chalcone derivatives of indole nucleus
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A series of previously unreported (2Z)-2-(1H-indol-1-yl)-3-(4-substituted phenyl)-1-phenylprop-2-en-1-one (5a–d) have been synthesized from easily accessible 2-(1H-indol-1-yl)-1-phenylethanone (3), which was obtained via a reaction of indole (1) with chloromethylphenyl ketone (2). The structures of the synthesized products have been elucidated using IR, 1H NMR, and mass-spectroscopic data and elemental analyses. The final products were screened for their antimicrobial activity. Excellent results were obtained against both bacteria and fungi. In conclusion, we have developed a novel, convenient and simple method for the preparation of indole – chalcone hybrid compounds via the reaction of indole derivative with carbonyl compounds in the presence of a strong base. The rapid conversion, excellent yield, utilization of a base, and operational simplicity are great advantages of the proposed method.
Key wordsMannich reaction chalcone indole derivatives antimicrobial activity
The authors are thankful to V. C. Banasthali University (Rajasthan) and Jamia Hamdard University (Delhi) for providing the spectral and analytical data. This paper is a part of Ph. D. Thesis of Rajani Chauhan.
- 2.J. F. Collinus Brit. Med. Bull., 21, 223 (1965)Google Scholar
- 3.V. W. M. Schach, H. Els J. Am. Chem. Soc., 83, 4678 (1961)Google Scholar
- 4.S. Garattini, L. Valzelli, Serotonin, Elsevier, (Amsterdam), 277 (1965)Google Scholar
- 7.A. Javad, S. Masoud, H. B. M. Farhad ARKIVOC., 11, 47– 58. (2006)Google Scholar
- 8.L. G. Thomas Heterocyclic Chemistry Edi-III pub. Longman,, (2001), pp. 240.Google Scholar
- 9.J. B. Harbone, T. J. Mabry and H. Mabry, The flavonoids, Academic press New york, (1976), pp. 187.Google Scholar
- 10.J. B. Harbone and T. J. Mabry The flavonoids: advances in research chapman and hall new York , (1982), pp 356.Google Scholar
- 11.M. T. Drexler, M. D. Amiridis, J. Catl., 136 (2003)Google Scholar
- 12.D. N. Dhar, The chemistry of Chalcones and related compounds, Wiley Interscience, New York., (1981), pp 8.Google Scholar
- 13.R Yogesh, Jorapur, Y. C. Dae Bull. Chem. Korean Soc, 27(3), 2006345.Google Scholar