Synthesis of potential anticancer agents: imidazo[4,5-c]pyridines and imidazo[4,5-b]pyridines.
Synthesis of potential anticancer agents: imidazo[4,5-c]pyridines and imidazo[4,5-b]pyridines.
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潜在抗癌剂的合成：咪唑并[4,5-c]吡啶和咪唑并[4,5-b]吡啶。
DOI：
10.1021/jm00393a011
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发表时间：
1987
影响因子：
7.3
通讯作者：
Rener,GA
中科院分区：
文献类型：
--
作者：
TempleJr,C;Rose,JD;Comber,RN;Rener,GA
1,2 -二氢吡啶[3,4 -6]吡嗪(1)是小鼠有丝分裂抑制剂，具有显著的抗肿瘤活性。此外，活性咪唑[4,5 -6]吡啶3被证明在有丝分裂时引起细胞积聚。研究了用乙硫甲酸环化4-（取代氨基）- 5,6 -二氨基吡啶合成3的同系物的途径。4,5 -或5,6 -二氨基吡啶与芳基醛的氧化环化分别生成[4,5 -c]和[4,5 -6]咪唑吡啶环体系。后者与6-（取代氨基）- 4,5 -二氨基吡啶反应得到1的咪唑[4,5 -c]吡啶环类似物。生物学研究表明，目标化合物的活性低于1和3。
The l, 2-dihydropyrido [3, 4-6] pyrazines (1) are mitotic inhibitors with significant antitumor activity in mice. Also, the active imidazo [4, 5-6] pyridine 3 was shown to cause the accumulation of cells at mitosis. Routes were developed for the synthesis of congeners of 3 by cyclization of 4-(substituted amino)-5, 6-diaminopyridines with ethylorthoformate. Oxidative cyclization of either 4, 5-or 5, 6-diaminopyridines with aryl aldehydes produced the [4, 5-c] and [4, 5-6] imidazopyridine ring systems, respectively. The latter reaction with 6-(substituted amino)-4, 5-diaminopyridines gave imidazo [4, 5-c] pyridine ring analogues of 1. Biological studies indicated that the target compounds were less active than 1 and 3.