A facile synthesis of 9-deaza analogue of olomoucine

被引：7

作者：

Capek, P ^{[1
]}

Otmar, M ^{[1
]}

Masojídková, M ^{[1
]}

Votruba, I ^{[1
]}

Holy, A ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2003年 / 68卷 / 04期

关键词：

pyrrolo[3,2-d] pyrimidines; 9-deazapurine; 2a,3,4,5-tetrahydro-2a,5,6,8-tetraazaacenaphthylene; CDK inhibitors; purines; cytokinins; antitumor activity; cytostatics;

D O I：

10.1135/cccc20030779

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Heating of 6-(benzylamino)-2-chloro-9-deazapurine (3) with ethanolamine afforded 6-( benzylamino)-2-[(2-hydroxyethyl) amino]-9-deazapurine (8). Its treatment with formaldehyde in alkaline solution, after protection of the OH group with DMTr, led to hydroxymethylation at position 9. Conversion of the hydroxymethyl group to methyl was performed by catalytic hydrogenation under simultaneous deprotection, which resulted in the formation of the 9-deaza analogue 1 of olomoucine. Compound 1 does not exhibit any significant in vitro cell growth inhibition of CCRF-CEM, HeLa and L-1210 cell lines. Cytostatic activity was found in 6-(benzylamino)-9-deazapurine (2) and its 2-chloro derivative 3 in CCRF-CEM cells with IC50 13.3 and 15.8 muM, respectively.

引用

页码：779 / 791

页数：13

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