3-AMINO-2-QUINOXALINECARBONITRILE - NEW FUSED QUINOXALINES WITH POTENTIAL CYTOTOXIC ACTIVITY
3-AMINO-2-QUINOXALINECARBONITRILE - NEW FUSED QUINOXALINES WITH POTENTIAL CYTOTOXIC ACTIVITY
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DOI：
10.1002/jhet.5570310506
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发表时间：
1994-09-01
影响因子：
2.4
通讯作者：
BARKER, AJ
中科院分区：
文献类型：
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作者：
MONGE, A;PALOP, JA;BARKER, AJ
以3-氨基-2-喹喔啉腈1，4-二氧化物1为起始原料，通过对2-氰基和3-氨基的化学修饰，合成了一系列新的喹喔啉衍生物。 硝化3-氨基-2-喹喔啉腈3得到7-硝基衍生物6。 3的重氮化得到3-氯化合物9。 从9获得2，3-喹喔啉二甲腈14。 哒嗪并[4，5-B]喹喔啉15和16是通过14与水合肼缩合制备的。 鉴定了一个三唑并[4，5-B]喹喔啉18、一个异噻唑并[4，5-B]喹喔啉20和两个吡唑并[3，4-B]喹喔啉21和22。 化合物作为细胞毒性剂在好氧和缺氧细胞中进行了测试。
Starting with 3-amino-2-quinoxalinecarbonitrile 1,4-dioxide 1, a new series of quinoxaline derivatives was prepared through chemical modifications of the 2-cyano and 3-amino groups. Nitration of 3-amino-2-quinoxalinecarbonitrile 3 afforded the 7-nitro derivative 6. Diazotation of 3 gave the 3-chloro compound 9. 2,3-Quinoxalinedicarbonitrile 14 was obtained from 9. Pyridazino[4,5-b]quinoxalines 15 and 16 were prepared by condensing 14 with hydrazine hydrate. A triazolo[4,5-b]quinoxaline 18, a isothiazolo[4,5-b]quinoxaline 20 and two pyrazolo[3,4-b]quinoxalines 21 and 22 were identified. Compounds were tested as cytotoxic agents both in oxic and in hypoxic cells.