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Synthesis and bioassay of a new class of disubstituted 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles

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Abstract

A new class of aroylethenesulfonylmethyl styryl oxadiazoles/thiadiazoles/triazoles and arylsulfonylethenesulfonylmethyl styryl oxadiazoles/thiadiazoles/triazoles were synthesized from the synthetic intermediates E-aroylethenesulfonylacetic acid methyl ester, E-arylsulfonylethenesulfonylacetic acid methyl ester and substituted cinnamic acids adopting conventional and ultrasonication methodologies. All the synthesized compounds were obtained in higher yields and in shorter reaction times in ultrasound irradiation method when compared with conventional method. The structures of all the compounds were characterized by IR, 1H NMR, 13C NMR and mass spectra. All the title compounds were tested for antimicrobial activity. The arylsulfonylethenesulfonylmethyl styryl azoles displayed higher antimicrobial activity than the aroylethenesulfonylmethyl styryl azoles. The compounds having triazole moiety showed greater activity than those with oxadiazole and thiadiazole. Amongst all the tested compounds unsubstituted and chloro substituted arylsulfonylethenesulfonyl methyl styryl triazoles are identified as potential antimicrobial agents particularly against B. subtilis and P.chrysogenum.

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Acknowledgements

The author M. Madhu Sekhar is grateful to University Grants Commission (UGC), New Delhi for the sanction of UGC-JRF fellowship. The authors are also thankful to Prof. T. Vijaya, Department of Botany, S.V. University and Tirupati for providing necessary facilities to carry out the antimicrobial activity.

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  1. Department of Chemistry, Sri Venkateswara University, Tirupati, AP, 517 502, India

    Mangali Madhu Sekhar, Gudi Yamini, Kuppi Reddy Gari Divya, Venkatapuram Padmavathi & Adivireddy Padmaja

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  1. Mangali Madhu Sekhar
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Madhu Sekhar, M., Yamini, G., Divya, K.R.G. et al. Synthesis and bioassay of a new class of disubstituted 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Med Chem Res 28, 1049–1062 (2019). https://doi.org/10.1007/s00044-019-02360-2

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