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PTSA-catalyzed straightforward novel approach for the synthesis of 1,2-bis(4-nitrophenyl)-1H-benzo[f]chromen-3-amine and the evaluation of their antituberculosis activity

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Abstract

A highly efficient protocol for the synthesis of 1,2-bis(4-nitrophenyl)-1H-benzo[f]chromen-3-amine derivative has been illustrated by a one-pot three-component reaction of aromatic aldehydes, 4-nitrophenyl acetonitrile and β-naphthol by using p-toluenesulfonic acid (PTSA) as the catalyst. PTSA is a mild, efficient, inexpensive Lewis acid catalyst which smoothly catalyzes the reaction. The synthesized compounds were predicted on the basis of IR, H1NMR, C13NMR and mass analysis data. The entire synthesized compounds (B-1–B-11) were evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H37RV strain using microplate Alamar blue assay, which shows promising results and activity expressed as MIC in µg/ml. The results indicate that most of the compounds exhibit comparable activity with standards pyrazinamide, streptomycin and ciprofloxacin against M. tuberculosis. Compound B-11 showed the best result with MIC 1.6 µg/ml, compared with the standard used, which is the main scientific finding of this new series of chromene-based compounds.

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Acknowledgement

The authors thank the Department of Science and Technology, New Delhi, for INSPIRE Fellowship (No. DST/INSPIRE Fellowship/2013/197).

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Authors and Affiliations

  1. Department of Agrochemicals and Pest Management, Shivaji University, Kolhapur, M.S., 416004, India

    Poojali P. Warekar, Priyanka T. Patil & Kirti T. Patil

  2. Medicinal Chemistry Research Laboratory, Department of Chemistry, Shivaji University, Kolhapur, M.S., 416004, India

    D. K. Jamale, Govind B. Kolekar & Prashant V. Anbhule

Authors
  1. Poojali P. Warekar
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  2. Priyanka T. Patil
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  3. Kirti T. Patil
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  4. D. K. Jamale
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  5. Govind B. Kolekar
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  6. Prashant V. Anbhule
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Correspondence to Prashant V. Anbhule.

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Warekar, P.P., Patil, P.T., Patil, K.T. et al. PTSA-catalyzed straightforward novel approach for the synthesis of 1,2-bis(4-nitrophenyl)-1H-benzo[f]chromen-3-amine and the evaluation of their antituberculosis activity. Res Chem Intermed 43, 4115–4127 (2017). https://doi.org/10.1007/s11164-017-2865-z

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  • DOI: https://doi.org/10.1007/s11164-017-2865-z

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