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Synthesis of Some Novel Pyrano[2,3-F]Chromenone Derivatives Publisher



Alizadeh BH1 ; Saeedi M2 ; Dehghan G3 ; Foroumadi A2 ; Shafiee A2
Authors
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Authors Affiliations
  1. 1. Iranian Research Institute of Plant Protection (IRIPP), Shahid Chamran Avenue, Yaman St. No 1, Tehran, Iran
  2. 2. Department of Medicinal Chemistry, Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, 14176, Iran
  3. 3. Department of Biology, Faculty of Natural Science, University of Tabriz, Tabriz, Iran

Source: Journal of the Iranian Chemical Society Published:2015


Abstract

A new series of pyrano[2,3-f]chromenone derivatives were synthesized starting from resorcinol. Resorcinol reacted with 3-chloropropanoic acid to give 7-hydroxychroman-4-one and reaction of the later compound with 2-methylbut-3-yn-2-ol led to the formation of 7-((2-methylbut-3-yn-2-yl)oxy)chroman-4-one. The obtained compound tolerated the cyclization reaction through Claisen rearrangement by heating in DMF to afford 8,8-dimethyl-2,3-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one. Reaction of the later compound with various aromatic aldehydes gave the title compounds in good yields. All products were evaluated for their cytotoxic activity on the blood tumor cell line K562 and compared to reference drug, etoposide. Most of them exhibited low inhibitory activity against tumor cell line and among them, the compound possessing three methoxy groups on aromatic ring showed better cytotoxic effect. © 2014 Iranian Chemical Society.