Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/102892
Title: Synthesis and Anti-Pancreatic Cancer Activity Studies of Novel 3-Amino-2-hydroxybenzofused 2-Phospha-γ-lactones
Authors: Balam, S. K.
Soora, Harinath, J.
Krishnammagari, S. K.
Gajjala, R. R.
Polireddy, K.
Baki, V. B.
Gu, W.
Valasani, K. R.
Avula, V. K. R.
Vallela, S.
Zyryanov, G. V.
Pasupuleti, V. R.
Cirandur, S. R.
Зырянов, Г. В.
Issue Date: 2021
Publisher: American Chemical Society
Citation: Synthesis and Anti-Pancreatic Cancer Activity Studies of Novel 3-Amino-2-hydroxybenzofused 2-Phospha-γ-lactones / S. K. Balam, J. Soora Harinath, S. K. Krishnammagari, et al. — DOI 10.1021/acsomega.1c00360 // ACS Omega. — 2021. — Vol. 6. — Iss. 17. — P. 11375-11388.
Abstract: A series of 3-amino-2-hydroxybenzofused 2-phosphalactones (4a-l) has been synthesized from the Kabachnik-Fields reaction via a facile route from a one-pot three-component reaction of diphenylphosphite with various 2-hydroxybenzaldehyes and heterocyclic amines in a new way of expansion. The in vitro anti-cell proliferation studies by MTT assay have revealed them as potential Panc-1, Miapaca-2, and BxPC-3 pancreatic cell growth inhibitors, and the same is supported by molecular docking, QSAR, and ADMET studies. The MTT assay of their SAHA derivatives against the same cell lines evidenced them as potential HDAC inhibitors and identified 4a, 4b, and 4k substituted with 1,3-thiazol, 1,3,4-thiadiazol, and 5-sulfanyl-1,3,4-thiadiazol moieties on phenyl and diethylamino phenyl rings as potential ones. Additionally, the flow cytometric analyses of 4a, 4b, and 4k against BxPC-3 cells revealed compound 4k as a lead compound that arrests the S phase cell cycle growth at low micromolar concentrations. The ADMET properties have ascertained their inherent pharmacokinetic potentiality, and the wholesome results prompted us to report it as the first study on anti-pancreatic cancer activity of cyclic α-aminophosphonates. Ultimately, this study serves as a good contribution to update the existing knowledge on the anticancer organophosphorus heterocyclic compounds and elevates the scope for generation of new anticancer drugs. Further, the studies like QSAR, drug properties, toxicity risks, and bioactivity scores predicted for them have ascertained the synthesized compounds as newer and potential drug candidates. Hence, this study had augmented the array of α-aminophosphonates by adding a new collection of 3-amino-2-hydroxybenzofused 2-phosphalactones, a class of cyclic α-aminophosphonates, to it, which proved them as potential anti-pancreatic cancer agents. ©
URI: http://hdl.handle.net/10995/102892
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85106601973
PURE ID: 22121758
5af4a2d2-dbec-4bfe-84bf-1616ad09da7c
ISSN: 24701343
DOI: 10.1021/acsomega.1c00360
metadata.dc.description.sponsorship: Mr. R.R.G. and Prof. S.R.C. thank Science and Engineering Research Board (SERB), India for providing financial assistance through a research project grant f.no.: SB/S1/OC-96/2013, Dt: 05-11-2014. Author S.K.B. thanks University Grants Commission (UGC), New Delhi, India for RFSMS (Research Fellowship in Sciences for Meritorious Students) Fellowship (F.4-1/2011, BSR-RFSMS-BSK) under Basic Scientific Research (BSR) Scheme. Authors V.K.R.A. and G.V.Z. are thankful to Ural Federal University for support and acknowledge the financial support of the Ministry of Science and Higher Education of the Russian Federation, Moscow, Russian Federation (grant no.: 075-15-2020-777).
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