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Current Organic Chemistry

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ISSN (Online): 1875-5348

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Research Article

Design, Synthesis, Reactions, Molecular Docking, Antitumor Activities of Novel Naphthopyran, Naphthopyranopyrimidines, and Naphthoyranotriazolopyrimidine Derivatives

Author(s): Rita Mohammed Ahmed Borik, Nasser Jaber Hadi Amri, Yousef Essa Mukhrish, Ashraf Hassan Fekry Abd El-Wahab*, Hany Mostafa Mohamed, Diaa Abd El-Samie Ibrahim and Ahmed Deeb Hassan Deeb

Volume 27, Issue 19, 2023

Published on: 13 November, 2023

Page: [1717 - 1727] Pages: 11

DOI: 10.2174/0113852728264994231018063921

Price: $65

Abstract

In ethanolic piperidine solution, the interaction of 6-bromonaphthalen-2-ol (1) with α- cyano-p-chlorocinnamonitrile (2a) or ethyl α-cyano-p-chlorocinnamate (2b) yielded 4Hnaphtho[ 2,1-b]pyran-3-carbonitrile (3a) and 4H-naphtho[2,1-b]pyran-3-carboxylate (3b). The naphthopyran derivatives (3a, b) reacted with electrophilic reagents afforded naphthopyranopyrimidines and naphthopyrano-triazolopyrimidine derivatives. The structures of the newly synthesized compounds are confirmed through spectral analysis using NMR, IR, and MS spectroscopy. The anticancer efficacy of all compounds was investigated against three cancer cell lines: MCF- 7, HeLa, and PC-3, along with a molecular docking study.

Keywords: 6-bromonaphthalen-2-ol, aromatic aldehydes, malononitrile, acetic anhydride, hydrazine hydrate, molecular docking, antitumor activities.

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