Selective Horner–Wittig/Nazarov vs. Knoevenagel/Nazarov Reactions in the Synthesis of Biologically Active 3-Aryl-Substituted 1-Indanones

Abstract 3-Aryl-1-indanones and a previously unknown group of 3-aryl-2-phosphoryl-1-indanones have been synthesized from β-ketophosphonates and aromatic aldehydes via corresponding chalcones, in a selective Horner–Wittig or Knoevenagel olefination, followed by a Nazarov cyclization. In preliminary t...

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Published in:Synlett 2017-01, Vol.28 (1), p.113-116
Main Authors: Szczęsna, Dorota, Koprowski, Marek, Różycka-Sokołowska, Ewa, Marciniak, Bernard, Bałczewski, Piotr
Format: Article
Language:English
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Summary:Abstract 3-Aryl-1-indanones and a previously unknown group of 3-aryl-2-phosphoryl-1-indanones have been synthesized from β-ketophosphonates and aromatic aldehydes via corresponding chalcones, in a selective Horner–Wittig or Knoevenagel olefination, followed by a Nazarov cyclization. In preliminary tests, the final compounds and the intermediate chalcones revealed anticancer activity against HeLa and K562 at the μM level.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588599