An improved procedure for synthesis of some new 1,3-diaryl-2-propen-1-ones using PEG-400 as a recyclable solvent and their antimicrobial evaluation

Bhaskar Dawane; Shankaraiah Konda; Baseer Shaikh; Raghunath Bhosale

doi:10.2478/v10007-009-0034-7

.blurhash-client-img { display: none !important; }

An improved procedure for synthesis of some new 1,3-diaryl-2-propen-1-ones using PEG-400 as a recyclable solvent and their antimicrobial evaluation

Acta Pharmaceutica

Volume 59 (2009): Issue 4 (December 2009)

By: Bhaskar Dawane, Shankaraiah Konda, Baseer Shaikh and Raghunath Bhosale

Open Access

|Nov 2009

Abstract

A simple and convenient route is described for the synthesis of novel hetero 1,3-diaryl-2-propen-1-ones (chalcones) by using recyclable PEG-400 as an alternative reaction solvent. The reaction is clean with excellent yield, shorter reaction time and reduces the use of volatile organic compounds (VOCs). All the synthesized compounds were evaluated for their antimicrobial activities against several pathogenic representatives.

References

J. R. Dimmock, D. W. Elias, M. A. Beazely and N. M. Kandepu, Bioactivities of chalcones, Curr. Med. Chem. 6 (1999) 1125-1150.10.2174/0929867306666220401182509
Search in Google Scholar
M. L. Go, X. Wu and L. X. Liu, Chalcones: An update on cytotoxic and chemoprotective properties, Curr. Med. Chem. 12 (2005) 483-499.
Search in Google Scholar
Z. Nowakowka, A review of anti-infective and anti-inflammatory chalcones, Eur. J. Med. Chem. 42 (2007) 125-137; DOI: 10.1016/j.ejmech.2006.09.019.10.1016/j.ejmech.2006.09.019
Search in Google Scholar
C. N. Khobragade, R. G. Bodade, M. S. Shine, R. R. Deepa, R. B. Bhosale and B. S. Dawane, Microbial and xanthine dehydrogenase inhibitory activity of some flavones, J. Enzym Inhib. Med. Chem. 3 (2008) 341-346; DOI: 10.1080/14756360701608585.10.1080/14756360701608585
Search in Google Scholar
S. Sogawa, Y. Nihro, H. Ueda, T. Miki, H. Matsumoto and T. Satoh, Protective effects of hydroxychalcones of free radical-induced cell damage, Biol. Pharm. Bull. 17 (1994) 251-256.10.1248/bpb.17.251
Search in Google Scholar
O. Nerya, R. Musa, S. Khatib, S. Tamir and J. Vaya, Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers, Phytochemistry 65 (2004) 1389-1395; DOI: 10.1016/j.phytochem.2004.04.016.10.1016/j.phytochem.2004.04.016
Search in Google Scholar
O. Prakash, A. Kumar, A. Sadana, R. Prakash, P. S. Singh, M. R. Claramunt, D. Sanz, I. Alkortac and J. Elguero, Study of the reaction of chalcone analogs of dehydroacetic acid and o-aminothiophenol: synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines, Tetrahedron 61 (2005) 6642-6651; DOI: 10.1016/j.tet.2005.03.035.10.1016/j.tet.2005.03.035
Search in Google Scholar
R. Y. Prasad, L. A. Rao, L. Prasoona, K. Murali and R. P. Kumar, Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2"-hydroxy naphthalen-1"-yl)-1,5-diphenyl-2-pyrazolines, Bioorg. Med. Chem. Lett. 15 (2005) 5030-5034; DOI: 10.1016/j.bmcl.2005.08.040.10.1016/j.bmcl.2005.08.040
Search in Google Scholar
S. Raghavan and K. Anuradha, Solid-phase synthesis of 1,4-diketones by thiazolium salt promoted addition of aldehydes to chalcones, Tetrahedron Lett. 43 (2002) 5181-5183; DOI: 10.1016/s0040-4039(02)00972-3.10.1016/S0040-4039(02)00972-3
Search in Google Scholar
B. A. Bohn, Introduction to Flavonoids, Harwood Academic, Amsterdam 1998.
Search in Google Scholar
R. L. Lankey and P. T. Anastas, Life-cycle approaches for assessing green chemistry technologies, Ind. Eng. Chem. Res. 41 (2002) 4498-4502; DOI: 10.1021/ie0108191.10.1021/ie0108191
Search in Google Scholar
P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York 1998.
Search in Google Scholar
B. S. Dawane, Y. B. Vibhute, S. G. Konda and M. R. Mali, Synthesis of some new 3-(substituted phenyl)-5-(9-anthryl)-2-pyrazolines, 1-phenyl-3-(substituted phenyl)-5-(9-anthryl)-2-pyrazolines and 2-(9-anthryl)-4-(substituted phenyl)-1,5-benzothiazepines as antibacterial agents, Asian J. Chem. 20 (2008) 4199-4204.
Search in Google Scholar
J. Chen, S. K. Spear, J. G. Huddleston and R. D. Rogers, Polyethylene glycol and solutions of polyethylene glycol as green reaction, Green Chem. 7 (2005) 64-82; DOI: 10.1039/b413546f.10.1039/b413546f
Search in Google Scholar
Vogel's Text book of Practical Organic Chemistry, 5th ed., Longman, London 1989.
Search in Google Scholar
B. S. Dawane and Y. B. Vibhute, Synthesis of some new hydroxyl acetophenones by using iodine and iodic acid, J. Ind. Chem. Soc. 77 (2000) 299.
Search in Google Scholar
M. H. Bahar and B. K. Sabata, Formylation of some heterocycles: An application of Vilsmeier-Haack reaction. Ind. J. Chem. 20B (1981) 328-329.
Search in Google Scholar
D. Shrinivasan, N. Sangeetha, T. Suresh and P. Lakshmanaperumalsamy, Antimicrobial activity of certain Indian medicinal plants used in folkloric medicine, J. Ethnopharmacol. 74 (2001) 217-220; DOI: 10.1016/s0378-8741(00)00345-7.10.1016/S0378-8741(00)00345-7
Search in Google Scholar

Articles in this issue

DOI: https://doi.org/10.2478/v10007-009-0034-7 | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075

Journal RSS Feed

Language: English

Page range: 473 - 482

Published on: Nov 16, 2009

Published by: Croatian Pharmaceutical Society

In partnership with: Paradigm Publishing Services

Publication frequency: 4 issues per year

Keywords:

1,3-diaryl-2-propen-1-ones,

PEG-400,

antimicrobial activity

Related subjects:

Pharmacy,

Pharmacy, other

© 2009 Bhaskar Dawane, Shankaraiah Konda, Baseer Shaikh, Raghunath Bhosale, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons License.

Volume 59 (2009): Issue 4 (December 2009)