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Molecules 2018, 23(8), 1981; https://doi.org/10.3390/molecules23081981

New 2-Oxoindolin Phosphonates as Novel Agents to Treat Cancer: A Green Synthesis and Molecular Modeling

1
Y. B. Chavan College of Pharmacy, Dr. Rafiq Zakaria Campus, Rauza Baug, Aurangabad, Maharashtra 431001, India
2
Departamento de Química Orgánica, Facultad de Ciencias, Universidad of Santiago De Compostela, Alfonso X el Sabio, 27002 Lugo, Spain
3
Department of Pharmaceutical Medicinal Chemistry, Srinath College of Pharmacy, Bajajnagar Aurangabad, Maharashtra 431136, India
*
Author to whom correspondence should be addressed.
Received: 25 June 2018 / Revised: 23 July 2018 / Accepted: 5 August 2018 / Published: 8 August 2018
(This article belongs to the Special Issue ECSOC-21)
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Abstract

The work reports the facile synthesis of novel α-aminophosphonate derivatives coupled with indole-2,3-dione moieties, namely the diethyl(substituted phenyl/heteroaryl)(2-(2-oxoindolin-3-ylidene)hydrazinyl)methylphosphonates derivatives 4(an). One-pot three component Kabachnik-Fields reactions were used to synthesize these derivatives. The reaction was carried out at room temperature by stirring in presence of ceric ammonium nitrate (CAN) as a green catalyst. The structures of the synthesized compounds were established by spectral studies. The synthesized derivatives 4(an) were evaluated for their in vitro anticancer activity against six human cancer cell lines by the SRB assay method. The cancer cell lines used in this research work are SK-MEL-2 (melanoma), MCF-7 (breast cancer), IMR-32 (neuroblastoma) MG-63 (human osteosarcoma), HT-29 (human colon cancer) and Hep-G2 (human hepatoma). All the synthesized derivatives inhibited the cell proliferation. Importantly, all the target compounds showed no cytotoxicity towards normal tissue cells (GI50 > 250 µM). A docking study was performed to predict the mode of action. Docking results indicate that the compounds have good binding with the enzyme tyrosine kinase as well as with microtubules, which makes them dual inhibitors. The result of in-silico bioavailability studies suggests that the compounds from the present series have good oral drug-like properties and are non-toxic in nature. In vivo acute oral toxicity study results indicate that the compounds can be considered safe, and therefore could be developed in the future as good anticancer agents or as leads for the design and synthesis of novel anticancer agents. View Full-Text
Keywords: indole-2,3-dione; α-aminophosphonates; in-vitro anticancer activity; ceric ammonium nitrate; docking indole-2,3-dione; α-aminophosphonates; in-vitro anticancer activity; ceric ammonium nitrate; docking
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Tiwari, S.V.; Sharif, N.S.; Gajare, R.I.; Vazquez, J.A.S.; Sangshetti, J.N.; Damale, M.D.; Nikalje, A.P.G. New 2-Oxoindolin Phosphonates as Novel Agents to Treat Cancer: A Green Synthesis and Molecular Modeling. Molecules 2018, 23, 1981.

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