1-(3-chlorobenzyl)-1H-indole-4-carbaldehyde | 1494603-14-3

• 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: 1-(3-chlorobenzyl)-1H-indole-4-carbaldehyde
• 英文别名: N-(3-chlorobenzyl)-4-indolecarbaldehyde；1-[(3-Chlorophenyl)methyl]indole-4-carbaldehyde
• CAS: 1494603-14-3
• 化学式: C₁₆H₁₂ClNO
• mdl: MFCD20177088
• 分子量: 269.73
• InChiKey: VKWZXILPJLPPQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-chlorobenzyl)-1H-indole-4-carbaldehyde 、 苦参碱 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 37.0h， 生成 14-[N-(3-chlorobenzyl)-4-indolemethylenyl]matrine
  参考文献：
  名称：

  苦参碱衍生物作为潜在抗癌药的设计，合成和生物学评价

  摘要：

  以苦参碱（1）为先导化合物，设计合成了一系列新的14-（N-取代-2-吡咯亚甲基）苦参碱和14-（N-取代-吲哚亚甲基）苦参碱衍生物，作为其潜在的抗癌剂。这些化合物的结构通过1 H NMR，13 C NMR和ESI-MS光谱分析进行表征。评价目标化合物对三种人类癌细胞系（SMMC-7721，A549和CNE2）的体外细胞毒性。结果显示，化合物A6和B21对具有IC 50的三种癌细胞系表现出最显着的抗癌活性值在3.42-8.05μM范围内，显示出比母体化合物（苦参碱）和阳性对照顺铂更好的活性。此外，膜联蛋白V-FITC / PI双重染色试验表明，化合物A6和B21可以剂量依赖性显着诱导SMMC-7721和CNE2细胞的凋亡。细胞周期分析还表明，化合物A6可导致SMMC-7721和CNE2细胞在G2 / M期的细胞周期停滞。

  DOI：

  10.1016/j.bmcl.2018.01.017
• 作为产物：
  描述：

  4-吲哚甲醛 、 间氯氯苄 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以76%的产率得到1-(3-chlorobenzyl)-1H-indole-4-carbaldehyde
  参考文献：
  名称：

  Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents

  摘要：

  A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the most potent cytotoxic activity against all tested cancer cell lines including multidrug resistant phenotype, which inhibits cancer cell growth with IC50 values ranging from 0.22 to 1.80 mu M. Furthermore, 49b significantly induced cell cycle arrest in G2/M phase and inhibited the polymerization of tubulin. Molecular docking analysis demonstrated the interaction of 49b at the colchicine binding site of tubulin. In experiments in vivo, 49b exerted potent anticancer activity in HepG2 human liver carcinoma in BALB/c nude mice. These results indicated these compounds are promising inhibitors of tubulin polymerization for the potential treatment of cancer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.028

文献信息

• 苦参碱吡咯、吲哚衍生物及其制备方法与应用
  申请人：广西大学

  公开号：CN108047226B

  公开（公告）日：2020-11-03

  本发明公开了一种苦参碱衍生物，包括吡咯、吲哚类苦参碱衍生物，还公开了该衍生物的制备方法和在制药中的应用。
• Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents
  作者：Guangcheng Wang、Chunyan Li、Lin He、Kai Lei、Fang Wang、Yuzi Pu、Zhuang Yang、Dong Cao、Liang Ma、Jinying Chen、Yun Sang、Xiaolin Liang、Mingli Xiang、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmc.2014.02.028

  日期：2014.4

  A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the most potent cytotoxic activity against all tested cancer cell lines including multidrug resistant phenotype, which inhibits cancer cell growth with IC50 values ranging from 0.22 to 1.80 mu M. Furthermore, 49b significantly induced cell cycle arrest in G2/M phase and inhibited the polymerization of tubulin. Molecular docking analysis demonstrated the interaction of 49b at the colchicine binding site of tubulin. In experiments in vivo, 49b exerted potent anticancer activity in HepG2 human liver carcinoma in BALB/c nude mice. These results indicated these compounds are promising inhibitors of tubulin polymerization for the potential treatment of cancer. (C) 2014 Elsevier Ltd. All rights reserved.
• Design, synthesis and biological evaluation of matrine derivatives as potential anticancer agents
  作者：Zheng Li、Mengyang Luo、Bin Cai、Lichuan Wu、Mengtian Huang、Haroon-Ur-Rashid、Jun Jiang、Lisheng Wang

  DOI：10.1016/j.bmcl.2018.01.017

  日期：2018.2

  Using matrine (1) as the lead compound, a series of new 14-(N-substituted-2-pyrrolemethylene) matrine and 14-(N-substituted-indolemethylene) matrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H NMR, 13C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity

  以苦参碱（1）为先导化合物，设计合成了一系列新的14-（N-取代-2-吡咯亚甲基）苦参碱和14-（N-取代-吲哚亚甲基）苦参碱衍生物，作为其潜在的抗癌剂。这些化合物的结构通过1 H NMR，13 C NMR和ESI-MS光谱分析进行表征。评价目标化合物对三种人类癌细胞系（SMMC-7721，A549和CNE2）的体外细胞毒性。结果显示，化合物A6和B21对具有IC 50的三种癌细胞系表现出最显着的抗癌活性值在3.42-8.05μM范围内，显示出比母体化合物（苦参碱）和阳性对照顺铂更好的活性。此外，膜联蛋白V-FITC / PI双重染色试验表明，化合物A6和B21可以剂量依赖性显着诱导SMMC-7721和CNE2细胞的凋亡。细胞周期分析还表明，化合物A6可导致SMMC-7721和CNE2细胞在G2 / M期的细胞周期停滞。