Triterpenoid Pyrazines and Benzopyrazines with Cytotoxic Activity
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- 作者：Milan Urban ; Jan Sarek ; Miroslav Kvasnica ; Iva Tislerova ; Marian Hajduch
- 刊名：Journal of Natural Products
- 出版年：2007
- 出版时间：April 2007
- 年：2007
- 卷：70
- 期：4
- 页码：526 - 532
- 全文大小：141K
- 年卷期：v.70,no.4(April 2007)
- ISSN：1520-6025
文摘
Twelve lupane, 18
-oleanane, and des-E-lupane derivatives (1a-5b) were either extracted from natural sources orsynthesized from betulinic acid (1a) and betulin (2). Compounds 1b, 1c, 3b, 3c, 4b, 4c, 5a, and 5b were then used asstarting materials for further synthesis of a series of pyrazines and benzopyrazines (6a-18); 20 of them are new (6a-6e, 7a-7d, and 10a-18). Activity of pyrazine 6a against the T-lymphoblastic leukemia cell line CEM encouraged usto synthesize several new esters (6b-6d) to study structure-activity relationships with respect to substitution of thecarboxyl group at position 28. The synthesized compounds were tested for cytotoxicity against a variety of cancer celllines of different histogenetic origin, and the results were compared with cytotoxicity of the known starting compounds.Significant cytotoxic activity against A 549, K 562, and multidrug-resistant K 562-tax cell lines was found in pyrazines6a, 6d, and 6e.
-oleanane, and des-E-lupane derivatives (1a-5b) were either extracted from natural sources orsynthesized from betulinic acid (1a) and betulin (2). Compounds 1b, 1c, 3b, 3c, 4b, 4c, 5a, and 5b were then used asstarting materials for further synthesis of a series of pyrazines and benzopyrazines (6a-18); 20 of them are new (6a-6e, 7a-7d, and 10a-18). Activity of pyrazine 6a against the T-lymphoblastic leukemia cell line CEM encouraged usto synthesize several new esters (6b-6d) to study structure-activity relationships with respect to substitution of thecarboxyl group at position 28. The synthesized compounds were tested for cytotoxicity against a variety of cancer celllines of different histogenetic origin, and the results were compared with cytotoxicity of the known starting compounds.Significant cytotoxic activity against A 549, K 562, and multidrug-resistant K 562-tax cell lines was found in pyrazines6a, 6d, and 6e.