6-chloro-1,4-dimethylcarbazole-3-carboxaldehyde | 1027067-29-3

• 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: 6-chloro-1,4-dimethylcarbazole-3-carboxaldehyde
• 英文别名: 6-chloro-1,4-dimethyl-9-H-carbazole-3-carbaldehyde；6-chloro-1,4-dimethyl-9H-carbazole-3-carbaldehyde
• CAS: 1027067-29-3
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: IZVVGZSQVLCHES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chloro-1,4-dimethylcarbazole-3-carboxaldehyde 在 磷酸 、 potassium carbonate 作用下， 反应 0.25h， 生成 9-Chloro-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
  参考文献：
  名称：

  Anticancer Specificity of Some Ellipticinium Salts against Human Brain Tumors in vitro

  摘要：

  Novel structure-activity relationships (SAR) distinct from known SAR for ellipticines have been revealed for certain ellipticinium salts. In particular, ellipticiniums such as the prototypical 9-methoxy-2-methylellipticinium (I- or OAc-) were found to be preferentially cytotoxic to the brain tumor cell line subpanel of the NCI 60 cell-line screening panel. Similar specificity also was apparent with 9-unsubstituted ellipticiniums, or others bearing 9-methyl or 9-chloro substituents. In contrast, 9-hydroxy-substituted ellipticiniums, as well as all nonquaternized ellipticines tested, were devoid of brain tumor specificity. Therefore, it did not appear that this unusual preference was correlated with the relative availability of redox cycling mechanisms, since redox cycling presumably is blocked in 9-methyl- and 9-chloroellipticiniums. Indeed, related investigations have indicated that the brain tumor specificity is mediated by preferential uptake and intracellular accumulation of the specific ellipticiniums. The present study further supports that the NCI in vitro ''disease-oriented'' primary screen can facilitate the discovery of novel, selectively cytotoxic leads for in vivo and mechanistic investigations.

  DOI：

  10.1021/jm00040a010
• 作为产物：
  描述：

  5-氯吲哚 在 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醇 、 邻二氯苯 为溶剂， 反应 4.67h， 生成 6-chloro-1,4-dimethylcarbazole-3-carboxaldehyde
  参考文献：
  名称：

  设计，合成，DNA结合研究以及新型取代的双咔唑衍生物对人神经胶质瘤U87 MG细胞系的抗癌能力。

  摘要：

  在这篇研究论文中，我们报告了新型取代的双咔唑衍生物的设计和合成，这些衍生物以1 H和13 C NMR，高分辨率质谱（HRMS）为特征。根据不同的取代基及其在双咔唑支架中的位置，报道了这些化合物的SAR研究。通过MTT测定24小时，评估化合物对人神经胶质瘤U87 MG细胞系的体外细胞毒性。所述IC 50是化合物（值30-35，48-53和54-62）在从1.00μM-500μM的浓度范围进行了计算。化合物34显示出最显着的体外细胞毒性（IC 50对人类神经胶质瘤U87 MG细胞株的抗药性为3.9 µM），被发现优于用于治疗脑肿瘤的标准药物，如替莫唑胺（IC 50 = 100 µM）和卡莫司汀（IC 50 = 18.2 µM）。为了确定化合物34与CT-DNA的结合方式，使用了各种生物物理技术，例如紫外分光光度计，荧光，圆二色性，粘度，拓扑异构酶测定和分子对接分析。我们的结果表明化合物34与C

  DOI：

  10.1016/j.bioorg.2020.103911

文献信息

• Design, synthesis, DNA binding studies and evaluation of anticancer potential of novel substituted biscarbazole derivatives against human glioma U87 MG cell line
  作者：Nitin Kumar、Neetika Lal、Vishal Nemaysh、Pratibha Mehta Luthra

  DOI：10.1016/j.bioorg.2020.103911

  日期：2020.7

  In this research paper, we report the design and synthesis of novel substituted biscarbazole derivatives which were characterized by 1H and 13C NMR, high resolution mass spectroscopy (HRMS). The SAR study of the compounds is reported based on different substituents and their positions in the biscarbazole scaffold. In vitro cytotoxicity of the compounds was evaluated against human glioma U87 MG cell

  在这篇研究论文中，我们报告了新型取代的双咔唑衍生物的设计和合成，这些衍生物以1 H和13 C NMR，高分辨率质谱（HRMS）为特征。根据不同的取代基及其在双咔唑支架中的位置，报道了这些化合物的SAR研究。通过MTT测定24小时，评估化合物对人神经胶质瘤U87 MG细胞系的体外细胞毒性。所述IC 50是化合物（值30-35，48-53和54-62）在从1.00μM-500μM的浓度范围进行了计算。化合物34显示出最显着的体外细胞毒性（IC 50对人类神经胶质瘤U87 MG细胞株的抗药性为3.9 µM），被发现优于用于治疗脑肿瘤的标准药物，如替莫唑胺（IC 50 = 100 µM）和卡莫司汀（IC 50 = 18.2 µM）。为了确定化合物34与CT-DNA的结合方式，使用了各种生物物理技术，例如紫外分光光度计，荧光，圆二色性，粘度，拓扑异构酶测定和分子对接分析。我们的结果表明化合物34与C
• Anticancer Specificity of Some Ellipticinium Salts against Human Brain Tumors in vitro
  作者：Edward M. Acton、Ven L. Narayanan、Prabhakar A. Risbood、Robert H. Shoemaker、David T. Vistica、Michael R. Boyd

  DOI：10.1021/jm00040a010

  日期：1994.7

  Novel structure-activity relationships (SAR) distinct from known SAR for ellipticines have been revealed for certain ellipticinium salts. In particular, ellipticiniums such as the prototypical 9-methoxy-2-methylellipticinium (I- or OAc-) were found to be preferentially cytotoxic to the brain tumor cell line subpanel of the NCI 60 cell-line screening panel. Similar specificity also was apparent with 9-unsubstituted ellipticiniums, or others bearing 9-methyl or 9-chloro substituents. In contrast, 9-hydroxy-substituted ellipticiniums, as well as all nonquaternized ellipticines tested, were devoid of brain tumor specificity. Therefore, it did not appear that this unusual preference was correlated with the relative availability of redox cycling mechanisms, since redox cycling presumably is blocked in 9-methyl- and 9-chloroellipticiniums. Indeed, related investigations have indicated that the brain tumor specificity is mediated by preferential uptake and intracellular accumulation of the specific ellipticiniums. The present study further supports that the NCI in vitro ''disease-oriented'' primary screen can facilitate the discovery of novel, selectively cytotoxic leads for in vivo and mechanistic investigations.