3-amino-6-nitro-β-carboline | 91943-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-amino-6-nitro-β-carboline
• 英文别名: 3-amino-6-nitro-9H-β-carboline；6-nitro-9H-pyrido[3,4-b]indol-3-amine
• CAS: 91943-60-1
• 化学式: C₁₁H₈N₄O₂
• 分子量: 228.21
• InChiKey: XJSRQXUXAPWHEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-6-nitro-β-carboline 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 58.0h， 生成 3,6-bis(benzylamino)-9H-β-carboline
  参考文献：
  名称：

  Structure–activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-β-carboline derivatives

  摘要：

  We synthesized 47 kinds of 3-amino- or 3-benzylamino-beta-carboline derivatives with a substituent on the 6-, 8-, or 6,8-carbon atoms and evaluated their antitumor activities for Hela S-3 and Sarcoma 180 cell lines using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Consequently, we succeeded to develop 3-benzylamino-8-methylamino-beta-carboline (17a) and 8-methylamino-3-(3-phenoxybenzyl)amino-beta-carboline (17c) with antitumor activity with IC50 values of 0.046, 0.032 mu M, respectively, against HeLa S-3 cell line, which are higher than that of previously reported 3-(3-phenoxybenzyl)amino-beta-carboline (10e) of 0.074 mu M. Furthermore, effects of Cl group at 6-carbon atom on the type of cell death was evaluated using 3-benzylamino-6-chloro-beta-carboline (10b), 3-benzylamino-beta-carboline (10d), N-(3-benzylamino)-6-chloro-9H-beta-carbolin-8-yl)benzamide (14g), and N-(3-benzylamino-9H-beta-carbolin-8-yl)benzamide (17b) to show no effect. Hoechst 33342 staining and DNA fragmentation assay suggested that these compounds induced cell death by apoptosis. In addition, using flow cytometry analysis, we established that the cell death pathway was through the arrest of the cell cycle in the G(2)/M phase. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.077
• 作为产物：
  描述：

  N-(6-nitro-9H-β-carbolin-3-yl)acetamide 在 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 以73%的产率得到3-amino-6-nitro-β-carboline
  参考文献：
  名称：

  Structure–activity relationship in the antitumor activity of 6-, 8- or 6,8-substituted 3-benzylamino-β-carboline derivatives

  摘要：

  We synthesized 47 kinds of 3-amino- or 3-benzylamino-beta-carboline derivatives with a substituent on the 6-, 8-, or 6,8-carbon atoms and evaluated their antitumor activities for Hela S-3 and Sarcoma 180 cell lines using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Consequently, we succeeded to develop 3-benzylamino-8-methylamino-beta-carboline (17a) and 8-methylamino-3-(3-phenoxybenzyl)amino-beta-carboline (17c) with antitumor activity with IC50 values of 0.046, 0.032 mu M, respectively, against HeLa S-3 cell line, which are higher than that of previously reported 3-(3-phenoxybenzyl)amino-beta-carboline (10e) of 0.074 mu M. Furthermore, effects of Cl group at 6-carbon atom on the type of cell death was evaluated using 3-benzylamino-6-chloro-beta-carboline (10b), 3-benzylamino-beta-carboline (10d), N-(3-benzylamino)-6-chloro-9H-beta-carbolin-8-yl)benzamide (14g), and N-(3-benzylamino-9H-beta-carbolin-8-yl)benzamide (17b) to show no effect. Hoechst 33342 staining and DNA fragmentation assay suggested that these compounds induced cell death by apoptosis. In addition, using flow cytometry analysis, we established that the cell death pathway was through the arrest of the cell cycle in the G(2)/M phase. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.077

文献信息

• Triazine-fused β-carbolines: a facile three-step, one-pot synthesis of novel 2-alkyl(aryl)amino and 2-dialkylamino-7H-[1,3,5]triazino [1',2':1,6]pyrido[3,4-b]indol-4-ones
  作者：Nicolas Primas、Hussein El-Kashef、Jean-Charles Lancelot、Aurélien Lesnard、Robert H. Dodd、Sylvain Rault

  DOI：10.3998/ark.5550190.0011.b14

  日期：——

  A straightforward approach to novel fused β-carbolines namely (1,3,5)triazino (1',2':1,6)pyrido(3,4-b)indol-4-ones is presented. The construction of these compounds was achieved by one-pot synthesis involving condensation of 3-amino-β-carbolines with ethoxycarbonyl isothiocyanate followed by amination of the resulting thioureas and finally thermal ring closure of the resulting guanidines which allowed

  提出了一种新的融合 β-咔啉即 (1,3,5)triazino (1',2':1,6)pyrido(3,4-b)indol-4-ones 的直接方法。这些化合物的构建是通过一锅合成实现的，包括 3-氨基-β-咔啉与乙氧基羰基异硫氰酸酯缩合，然后将所得硫脲胺化，最后使所得胍热闭环，从而获得未报道的标题杂环。