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Regioselective synthesis of 3,4-diaryl-5-unsubstituted isoxazoles, analogues of natural cytostatic combretastatin A4.
Chernysheva, Natalia B; Maksimenko, Anna S; Andreyanov, Fedor A; Kislyi, Victor P; Strelenko, Yuri A; Khrustalev, Victor N; Semenova, Marina N; Semenov, Victor V.
Afiliación
  • Chernysheva NB; N. D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prospect, 119991, Moscow, Russian Federation. Electronic address: info@chemblock.com.
  • Maksimenko AS; N. D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prospect, 119991, Moscow, Russian Federation; D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation. Electronic address: chem.annamaks@gmail.com.
  • Andreyanov FA; N. D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prospect, 119991, Moscow, Russian Federation. Electronic address: andreyanovfeodor@gmail.com.
  • Kislyi VP; N. D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prospect, 119991, Moscow, Russian Federation. Electronic address: vkislyi@yandex.ru.
  • Strelenko YA; N. D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prospect, 119991, Moscow, Russian Federation. Electronic address: strel@ioc.ac.ru.
  • Khrustalev VN; Faculty of Science, RUDN University, 6 Miklukho-Maklay Street, 117198, Moscow, Russian Federation; A. N. Nesmeyanov Institute of Organoelement Compounds RAS, 28 Vavilov Street, 119991, Moscow, Russian Federation. Electronic address: vkh@xray.ineos.ac.ru.
  • Semenova MN; N. K. Koltzov Institute of Developmental BiologyRAS, 26 Vavilov Street, 119334, Moscow, Russian Federation. Electronic address: ms@chemical-block.com.
  • Semenov VV; N. D. Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prospect, 119991, Moscow, Russian Federation. Electronic address: vs@zelinsky.ru.
Eur J Med Chem ; 146: 511-518, 2018 Feb 25.
Article en En | MEDLINE | ID: mdl-29407976
4,5-Diarylisoxazoles are potent antiproliferative tubulin-targeting agents. Their isomeric 3,4-diaryl-5-unsubstituted isoxazoles are hardly accessible. The synthesis of 3,4-diaryl-5-unsubstituted isoxazoles 13 was designed based on a condensation of arylbenzaldehydes, arylnitromethanes, and ethoxycarbonylmethylpyridinium bromide followed by a selective one-step transformation of intermediate 3,4-diaryl-5-ethoxycarbonyl-4,5-dihydroisoxazole 2-oxides 8. The orientation of aryl rings in relation to isoxazole heterocycle was confirmed by X-ray crystallography. Targeted compounds were evaluated for antimitotic microtubule destabilizing activity using a phenotypic sea urchin embryo assay. 3-(4-Methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)isoxazole 13e and 13h with a single methoxy substituent were the most potent. Compound 13e showed strong cytotoxicity in NCI60 screen with GI50 for NCI-H522 human lung cancer cell line of 0.023 µM.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Estilbenos / Productos Biológicos / Isoxazoles / Antineoplásicos Límite: Humans Idioma: En Revista: Eur J Med Chem Año: 2018 Tipo del documento: Article Pais de publicación: Francia
Texto completo
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Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Estilbenos / Productos Biológicos / Isoxazoles / Antineoplásicos Límite: Humans Idioma: En Revista: Eur J Med Chem Año: 2018 Tipo del documento: Article Pais de publicación: Francia