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Current Organic Chemistry

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

DOI: 10.2174/0113852728264994231018063921

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

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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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