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Nano Sb2O3 catalyzed green synthesis, cytotoxic activity, and molecular docking study of novel α-aminophosphonates

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Abstract

Green synthesis of a series of novel dialkyl (aryl substituted)(2-fluoro-4-((2-methylcarbamoyl)pyridine-4-yl)oxy)phenyl)amino)methyl)phosphonates is accomplished by a simple and an efficient one pot three component reaction of 3-(4-amino-3-fluorobenzyl)-N-methylbenzamide with different substituted aromatic aldehydes and dialkyl phosphite in the presence of nano Sb2O3 catalyst under solvent free conditions at 40–50 °C to obtain the title compounds. Excellent isolated product yields are obtained (85–95%) with high purity within shorter reaction times (30–60 min). The title compounds are characterized by IR, 1H, 13C, 31P-NMR and mass spectral data. The synthesized compounds are screened for their anticell-proliferation activity on seven cell lines, Control cells–HEK293 (human embryonic kidney), DU-145 (human prostate adenocarcinoma), MCF-7 (human ER+/PR+/Her2− breast cancer), MDA-MB-231 (human ER−/PR−/Her2− breast cancer), Mia-Paca-2 (human pancreatic carcinoma), HeLa (human cervical cancer) cells as well as HepG2 (human hepatocellular carcinoma) cancer cell lines using Sulforhodamine B (SRB) assay method. Docking studies were carried out for all these synthesized compounds against topoisomerase-II by using Auto dock method. Doxorubicin was taken as standard. Compounds 4a, 4c, 4d, 4e, 4h, 4i, 4k, and 4l exhibited higher cytotoxic activity than the standard doxorubicin.

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Acknowledgements

We thank to Professor C. Devendhranath Reddy for his helpful discussions and also acknowledge DST-PURSE Centre, S.V. University, Tirupati for providing instrumental analysis and funding to one of the authors Mr. Mohan Gundluru through SRF (File No: 17118-UGC-III(3)/ DST-PURSE 2nd Phase/2017, Dt: 23-08-2018).

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Authors and Affiliations

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

    Sreelakshmi Poola, Maheshwara Reddy Nadiveedhi, Santhisudha Sarva, Mohan Gundluru, Saichaithanya Nagaripati, Mahammad Sadik Shaik, Nagaraju Chamarthi & Suresh Reddy Cirandur

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

    Peddanna Kotha

  3. Institute of Food Security and Sustainable Agriculture, Universiti Malaysia Kelantan Kampus Jeli, Locked Bag 100, Jeli, Kelantan, 17600, Malaysia

    Suresh Reddy Cirandur

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  1. Sreelakshmi Poola
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  2. Maheshwara Reddy Nadiveedhi
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Correspondence to Suresh Reddy Cirandur.

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Poola, S., Nadiveedhi, M.R., Sarva, S. et al. Nano Sb2O3 catalyzed green synthesis, cytotoxic activity, and molecular docking study of novel α-aminophosphonates. Med Chem Res 28, 528–544 (2019). https://doi.org/10.1007/s00044-019-02302-y

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