Synthesis of a regio-isomer of kealiiquinone, a marine benzimidazole alkaloid

Autor:	Yoshitaka Ohishi, Naoki Tsuno, Shunsaku Ohta, Ikuo Kawasaki, Masayuki Yamashita, Seikou Nakamura
Rok vydání:	2001
Předmět:	Benzimidazole chemistry.chemical_compound chemistry Mechanism of action Stereochemistry Yield (chemistry) Alkaloid medicine medicine.symptom Human cancer
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :429-436
ISSN:	1364-5463 1472-7781
DOI:	10.1039/b007560o
Popis:	Treatment of 1,3-dialkyl-2-(phenylthio)benzimidazolium salts 3 and 1,3-dialkyl-2-phenylthio-1H-imidazolium salts 7 with aq. K2CO3 gives 1,3-dialkyl-1,3-dihydrobenzimidazol-2-ones 4 and 1,3-dialkyl-1,3-dihydroimidazol-2-ones 8, respectively, in 22–94% yield. A regio-isomer 17 of kealiiquinone, a marine benzimidazole alkaloid, where the 4-methoxyphenyl group at the 4-position migrates to the 9-position, is synthesized by application of the reaction. Cytotoxity of 17 and kealiiquinone against 39 human cancer cells is evaluated. They have weak activity but a unique mechanism of action.
Databáze:	OpenAIRE
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