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One-pot green synthesis and cytotoxicity of new α-aminophosphonates

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Abstract

A novel series of α-aminophosphonates containing the trifluoromethyl aniline moiety were obtained in high yields by condensation of 2-methyl-3-trifluoromethyl aniline, aryl/heteroaryl aldehydes and dimethylphosphite in the presence of chitosan as a catalyst. The molecular modeling studies revealed their important structural features of binding affinities towards the target enzyme. The cytotoxicity of these compounds was evaluated against PC-3(prostate cancer), MCF-7 (breast cancer), HeLa(cCervix Cancer), U973, K562 and HL60 human lLeukemia cell lines. Compound 4k with a pyrene moiety showed high potency against a breast cancer cell line, while compounds 4g and 4k exhibited more promising cytotoxicity against U973, K562 and HL60 cell lines.

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Acknowledgements

The authors express thanks to Prof. C. Devendranath Reddy, Department of Chemistry, Sri Venkateswara University, Tirupati, for his helpful discussions, acknowledge the DST-SERB, New Delhi, India for providing financial support through the Project File No: SB/S1/OC-96/2013, dated: 05-11-2014) and the Anti-Cancer Drug screening facility in ACTREC, Tata Memorial Centre, Navi Mumbai for the in vitro SRB assay of compounds for anti-cancer activity.

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Authors and Affiliations

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

    Kandula Madhu Kumar Reddy, Shaik Mahammad Sadik, Nagaripati Saichaithanya, Nemallapudi Bakthavatchala Reddy, Gundala Sravya & Cirandur Suresh Reddy

  2. Department of Bio-Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh, 517 502, India

    Kotha Peddanna

  3. Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, Yekaterinburg, Russian Federation, 620002

    Nemallapudi Bakthavatchala Reddy, Gundala Sravya & Zyryanov Grigory V

  4. Ural Division of the Russian Academy of Sciences, I. Ya. Postovskiy Institute of Organic Synthesis, 22 S. Kovalevskoy Street, Yekaterinburg, Russian Federation, 620219

    Zyryanov Grigory V

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  1. Kandula Madhu Kumar Reddy
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  2. Shaik Mahammad Sadik
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  3. Nagaripati Saichaithanya
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  4. Kotha Peddanna
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  5. Nemallapudi Bakthavatchala Reddy
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  6. Gundala Sravya
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  7. Zyryanov Grigory V
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  8. Cirandur Suresh Reddy
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Correspondence to Cirandur Suresh Reddy.

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Reddy, K.M.K., Sadik, S.M., Saichaithanya, N. et al. One-pot green synthesis and cytotoxicity of new α-aminophosphonates. Res Chem Intermed 43, 7087–7103 (2017). https://doi.org/10.1007/s11164-017-3060-y

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  • DOI: https://doi.org/10.1007/s11164-017-3060-y

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