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Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents

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Abstract

A series of novel 2-amino 3-cyano 4-aryl pyrano[2,3H]chrysin derivatives (3a–m) were efficiently synthesized by one-pot three-component reaction of aromatic aldehydes, malononitrile and chrysin and characterized by 1H NMR, 13C NMR and mass spectral data. All the newly synthesized compounds were evaluated for their in vitro antimicrobial activity (antibacterial and antifungal). Among the tested compounds, 3a, 3g, 3h, 3j and 3k showed potent antibacterial activity compared to ciprofloxacin and the compounds 3a, 3g, 3h, 3i and 3k showed excellent antifungal activity compared to itrazole. The compounds 3a, 3g, 3h and 3k exhibited potent antimicrobial activity against all the selected pathogenic bacteria and fungi and emerged as potential molecules for further development. In addition, molecular modeling studies also performed to delineate the putative binding mode of these compounds. All of these chrysin derivatives (3a–m) obeyed the Lipinski’s “rule of five” and have drug-likeness. Docking scores with appreciable binding energy values also exactly correlated with the experimental antimicrobial activity. The chemscore estimated by GOLD software was found to have a good correlation with the experimental inhibitory activity.

Graphical Abstract

Docking of compound 3g with protein

A series of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives (3a–m) has been synthesized and evaluated for their antimicrobial activity along with molecular modeling studies

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Acknowledgments

One of the authors Ch. S. Reddy is thankful to CSIR, New Delhi, for the financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, SR and BGNR Government College, Khammam, 507 002, India

    P. Ramesh

  2. Department of Chemistry, Kakatiya University, Warangal, 506 009, India

    Ch. Sanjeeva Reddy

  3. Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India

    K. Suresh Babu

  4. Department of Chemistry, Nizams PG College, Osmania University, Hyderabad, 500 007, India

    P. Ramesh & P. Muralidhar Reddy

  5. Department of Chemistry, Osmania University, Hyderabad, 500 007, India

    V. Srinivasa Rao & T. Parthasarathy

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  1. P. Ramesh
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  2. Ch. Sanjeeva Reddy
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  3. K. Suresh Babu
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  4. P. Muralidhar Reddy
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  5. V. Srinivasa Rao
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  6. T. Parthasarathy
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Correspondence to Ch. Sanjeeva Reddy, K. Suresh Babu or P. Muralidhar Reddy.

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Ramesh, P., Reddy, C.S., Suresh Babu, K. et al. Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents. Med Chem Res 24, 3696–3709 (2015). https://doi.org/10.1007/s00044-015-1396-7

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