Synthetic Transformations of Higher Terpenoids. XXVI. 16-Acetylaminomethyllabdanoids and Their Cytotoxicity

Synthetic Transformations of Higher Terpenoids. XXVI. 16-Acetylaminomethyllabdanoids and Their Cytotoxicity Научная публикация

Журнал

Russian Journal of Bioorganic Chemistry
ISSN: 1068-1620

Вых. Данные

Год: 2012, Том: 38, Номер: 1, Страницы: 107-115 Страниц : DOI: 10.1134/S1068162011060082

Ключевые слова

plant diterpenoids; lambertianic acid; methyl 16-aminomethyllambertianate; omega-amino acids; tumor cells

Авторы

Kharitonov Yu. V. ¹ , Shul'ts E. E. ¹ , Shakirov M. M. ¹ , Pokrovsky M. A. ² , Pokrovsky A. G. ² , Tolstikov G. A. ¹

Организации

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Novosibirsk Organ Chem Inst, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk, Russia

Coupling of methyl 16-aminomethyllambertianate with N-Boc-protected omega-amino acids resulted in 16-(N-Boc-aminononan)- and 16-(N-Boc-aminoundecan)amidomethyllabdanoids. Interaction of methyl aminomethyllambertianate with bicyclo[2.2.1]hept-5-en-2,3-dicarboxylic acid anhydride led to the amide of bicyclo[2.2.1]heptan-1,2-dicarboxylic acid with a labdanoid substituent. Reaction of methyl 16-aminomethyllambertianate with chloroacetyl chloride resulted in methyl 16-(chloroacetylaminomethyl)lambertianate; coupling of the latter with methyl esters of amino acids gave the corresponding amides of methyl lambertianate. The compounds obtained were more cytotoxic toward CEM-13, MT-4, and U-937 tumor cell lines as compared with lambertianic acid; the dose inhibiting tumor cell viability by 50% (CCID50) of the more active compounds was 3.9-9.9 mu M.

Kharitonov Y.V. , Shul'ts E.E. , Shakirov M.M. , Pokrovsky M.A. , Pokrovsky A.G. , Tolstikov G.A.
Synthetic Transformations of Higher Terpenoids. XXVI. 16-Acetylaminomethyllabdanoids and Their Cytotoxicity
Russian Journal of Bioorganic Chemistry. 2012. V.38. N1. P.107-115. DOI: 10.1134/S1068162011060082 WOS Scopus РИНЦ

Опубликована в печати:	1 янв. 2012 г.
Опубликована online:	28 янв. 2012 г.

Web of science	WOS:000304409500016
Scopus	2-s2.0-84861169504
РИНЦ	17985667
OpenAlex	W1988051156