N-cyclohexyl-3-thia-6,10b-diazacyclopenta[c]fluorene-9-carboxamidine hydrochloride | 1044509-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-cyclohexyl-3-thia-6,10b-diazacyclopenta[c]fluorene-9-carboxamidine hydrochloride
• 英文别名: N'-morpholin-4-yl-5-thia-1,10-diazatetracyclo[7.7.0.02,6.011,16]hexadeca-2(6),3,7,9,11(16),12,14-heptaene-14-carboximidamide;hydrochloride
• CAS: 1044509-83-2
• 化学式: C₁₈H₁₇N₅OS*ClH
• 分子量: 387.893
• InChiKey: LBIWTVWMWIMRJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  E-N'-morpholin-4-yl-2-(2-thiophen-2-ylvinyl)-3H-benzimidazole-5(6)-carboxamidine hydrochloride 在 air 、 碘 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-cyclohexyl-3-thia-6,10b-diazacyclopenta[c]fluorene-8-carboxamidine hydrochloride 、 N-cyclohexyl-3-thia-6,10b-diazacyclopenta[c]fluorene-9-carboxamidine hydrochloride
  参考文献：
  名称：

  Novel Amidino-Substituted Thienyl- and Furylvinylbenzimidazole: Derivatives and Their Photochemical Conversion into Corresponding Diazacyclopenta[c]fluorenes. Synthesis, Interactions with DNA and RNA, and Antitumor Evaluation. 4

  摘要：

  Synthesis of novel nonfused amidino-substituted thienyl- and furyl vinylbenzimidazole: derivatives and their photochemical cyclization into corresponding diazacyclopenta[c]fluorenes is described. All studied compounds showed prominent growth inhibitor effect. The fused compounds showed stronger activity than nonfused ones, whereby imidazolyl-substituted compound 11 proved to be the most active one. Besides, it induced strong G2/M arrest of the cell cycle followed by drastic apoptosis, which is in accordance with the DNA intercalative binding mode determined by the spectroscopic studies. Nonfused derivatives induced strong S phase arrest of the cell cycle followed by apoptosis that together with DNA minor groove binding mode pointed to topoisomerase I inhibition. In addition, all nonfused compounds revealed pronounced selectivity toward tumor cells in comparison with nontumor cells. Oil the basis of the presented results, both nonfused and fused thiophene-containing, imidazolyl derivatives Should be considered as promising lead compounds for further investigation.

  DOI：

  10.1021/jm8000423

文献信息

• Novel Amidino-Substituted Thienyl- and Furylvinylbenzimidazole: Derivatives and Their Photochemical Conversion into Corresponding Diazacyclopenta[<i>c</i>]fluorenes. Synthesis, Interactions with DNA and RNA, and Antitumor Evaluation. 4
  作者：Marijana Hranjec、Ivo Piantanida、Marijeta Kralj、Lidija Šuman、Krešimir Pavelić、Grace Karminski-Zamola

  DOI：10.1021/jm8000423

  日期：2008.8.1

  Synthesis of novel nonfused amidino-substituted thienyl- and furyl vinylbenzimidazole: derivatives and their photochemical cyclization into corresponding diazacyclopenta[c]fluorenes is described. All studied compounds showed prominent growth inhibitor effect. The fused compounds showed stronger activity than nonfused ones, whereby imidazolyl-substituted compound 11 proved to be the most active one. Besides, it induced strong G2/M arrest of the cell cycle followed by drastic apoptosis, which is in accordance with the DNA intercalative binding mode determined by the spectroscopic studies. Nonfused derivatives induced strong S phase arrest of the cell cycle followed by apoptosis that together with DNA minor groove binding mode pointed to topoisomerase I inhibition. In addition, all nonfused compounds revealed pronounced selectivity toward tumor cells in comparison with nontumor cells. Oil the basis of the presented results, both nonfused and fused thiophene-containing, imidazolyl derivatives Should be considered as promising lead compounds for further investigation.