Synthesis of some novel pyrano[2,3-f]chromenone derivatives

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• 作者：Babak Heidary Alizadeh (1)
  Mina Saeedi (2)
  Gholamreza Dehghan (3)
  Alireza Foroumadi (2)
  Abbas Shafiee (2)
  
  1. Iranian Research Institute of Plant Protection (IRIPP) ; Shahid Chamran Avenue ; Yaman St. No 1 ; PO. Box ; 1454 ; Tehran ; Iran
  2. Department of Medicinal Chemistry ; Faculty of Pharmacy and Pharmaceutical Sciences Research Center ; Tehran University of Medical Sciences ; 14176 ; Tehran ; Iran
  3. Department of Biology ; Faculty of Natural Science ; University of Tabriz ; Tabriz ; Iran
  
• 关键词：Pyranochromenone ; Resorcinol ; Claisen rearrangement
• 刊名：Journal of the Iranian Chemical Society
• 出版年：2015
• 出版时间：April 2015
• 年：2015
• 卷：12
• 期：4
• 页码：605-612
• 全文大小：419 KB
• 参考文献：1. J. Hepworth, in / Comprehensive Heterocyclic Chemistry, ed. by A.R. Katrizky, C.W. Rees (Pergamon, Oxford, 1984), vol. 3, p. 737
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• 刊物主题：Analytical Chemistry; Inorganic Chemistry; Physical Chemistry; Biochemistry, general; Organic Chemistry;
• 出版者：Springer Berlin Heidelberg
• ISSN：1735-2428

文摘

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.