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Photodimerization of heteroaryl chalcones: comparative antimicrobial activities of chalcones and their photoproducts

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Abstract

The heterocyclic analogues of chalcones were synthesized by Claisen Schmidt reaction of (a) benzaldehyde with 2-acetylfurane, 2-acetylpyrrole and 2-acetylthiophene and (b) acetophenone with furfural, thiophene-2-carbaldehyde and pyrrole-2-carbaldehyde. The photolysis of class (a) and (b) chalcones under UV lamp gave different products. The stereoselective photodimerization of 1-(furane-2-yl)-3-phenylprop-2-en-1-one (1), 3-phenyl-1-(1H-pyrrole-2-yl)-prop-2-en-1-one (2) gave β-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (furane-2-yl methanone) (7), (3,4-diphenylcyclobutane-1,2-diyl)bis ((1H-pyrrol-2-yl) methanone) (8) by syn head-to-head coupling whereas 3-phenyl-1-(thiophen-2-yl)-prop-2-en-1-one (3) gave δ-truxinic type dimers, (3,4-diphenylcyclobutane-1,2-diyl)bis (thiophen-2-yl methanone) (9) by anti head-to-head coupling. The photolytic products of 3-(furane-2-yl)-1-phenylprop-2-en-1-one (4), 1-phenyl-3-(thiophen-2-yl)-prop-2-en-1-one (5) and 1-phenyl-3-(1H-pyrrole-2-yl)- prop-2-en-1-one (6) were identified as corresponding 1,6-di(furane-2-yl)-3,4-diphenylhexa-1,5-diene-3,4-diol (10), 3,4-diphenyl-1,6-di(thiophen-2-yl)hexa-1,5-diene-3,4-diol (11) and 3,4-diphenyl-1,6-di(1H-pyrrol-2-yl)hexa-1,5-diene-3,4-diol (12) pinacol dimers. The antibacterial and antifungal activity of the precursor chalcones and the dimeric products showed antimicrobial activities of different extents with respect to individual compounds. In general, photolysis of heteroaryl chalcones causes the depletion of antimicrobial activity.

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Acknowledgments

We are thankful to the Head, School of Studies in Chemistry, Vikram University Ujjain for providing facilities. Constructive suggestions from Dr. Manmohan L. Satnami, School of Studies in Chemistry, Pt. Ravishankar Shukla University, Raipur is acknowledged with appreciation. We are thanks to the Head, Institute of Environment Management and Plant Science, Vikram University, Ujjain for providing microorganisms.

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Authors and Affiliations

  1. Department of Chemistry, Government College Barnagar, Ujjain, Madhya Pradesh, India, 456010

    Rekha Nagwanshi

  2. School of Studies in Chemistry & Biochemistry, Vikram University, Ujjain, Madhya Pradesh, India, 456010

    Meena Bakhru & Shubha Jain

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  1. Rekha Nagwanshi
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  2. Meena Bakhru
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  3. Shubha Jain
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Correspondence to Rekha Nagwanshi.

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Nagwanshi, R., Bakhru, M. & Jain, S. Photodimerization of heteroaryl chalcones: comparative antimicrobial activities of chalcones and their photoproducts. Med Chem Res 21, 1587–1596 (2012). https://doi.org/10.1007/s00044-011-9667-4

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