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An efficient synthesis of isoxazoline libraries of thiophene analogs and its antimycobacterial investigation

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Abstract

Synthesis of novel thiophene substituted isoxazoline libraries is currently of high interest. Here, we have reported detailed syntheses of 2,5-dichlorothiophene, 5-chloro-2-(benzylthio)thiophene, and 5-chlorothiophene-2-sulphonamide substituted analogs of isoxazoline from chalcones catalyzed by NaOH in PEG-400 as green solvent. In vitro antimycobacterial and antimicrobial activity of newly synthesized compounds were investigated. Compounds 2j, 2k, and 2l showed excellent activity against Mycobacterium tuberculosis and other Mycobacterium strains tested. Compounds 2a–2c, 2i showed excellent activity against all bacterial and fungal species tested. The isoxazoline scaffold synthesized in the present study may be useful in the development of novel new antimicrobial agents.

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An efficient synthesis of isoxazoline libraries of thiophene analogs and its antimycobacterial investigation.

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Acknowledgments

The author RDK is sincerely thankful to the CSIR, New Delhi for JRF. Authors are also thankful to Director Vijayshree Chemicals Hyderabad for gifting 2-n-butyl-4-chloro-5-formyl imidazole (BCFI) and Director, Indian Institute of Chemical Technology Hyderabad, India for providing analytical support.

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Authors and Affiliations

  1. School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded, MS, India

    Gajanan G. Mandawad, Rahul D. Kamble, Shrikant V. Hese & Bhaskar S. Dawane

  2. School of Life Sciences, Swami Ramanand Teerth Marathwada University, Nanded, MS, India

    Rahul A. More & Rajesh N. Gacche

  3. Department of Biochemistry, University of Pune, Pune, MS, India

    Kisan M. Kodam

Authors
  1. Gajanan G. Mandawad
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  2. Rahul D. Kamble
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  3. Shrikant V. Hese
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  4. Rahul A. More
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  5. Rajesh N. Gacche
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  6. Kisan M. Kodam
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  7. Bhaskar S. Dawane
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Corresponding author

Correspondence to Bhaskar S. Dawane.

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Mandawad, G.G., Kamble, R.D., Hese, S.V. et al. An efficient synthesis of isoxazoline libraries of thiophene analogs and its antimycobacterial investigation. Med Chem Res 23, 4455–4463 (2014). https://doi.org/10.1007/s00044-014-1016-y

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  • DOI: https://doi.org/10.1007/s00044-014-1016-y

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