1-(3-bromobenzyl)-1H-indole-4-carbaldehyde | 1490413-34-7

• 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-bromobenzyl)-1H-indole-4-carbaldehyde
• 英文别名: N-(3-bromobenzyl)indol-4(1H)-ylcarbaldehyde；1-[(3-Bromophenyl)methyl]indole-4-carbaldehyde
• CAS: 1490413-34-7
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: HBONNKDPMRVFGR-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：
  0.06
• 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-bromobenzyl)-1H-indole-4-carbaldehyde 、 槐定碱 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以38%的产率得到14-[N-(3-bromobenzyl)-1H-indol-4-ylmethylene]sophoridine
  参考文献：
  名称：

  槐定碱吡咯、吲哚类衍生物及其制备方法与应 用

  摘要：

  一种槐定碱吡咯、吲哚类衍生物，本发明公开了该类化合物的化学结构，还公开了该类化合物的制备方法。本通过在体外抗肿瘤活性研究说明该类化合物具有发展前景的抗肿瘤药物，给广大的癌症患者提供多一种治疗的可能。

  公开号：

  CN108358923B
• 作为产物：
  描述：

  4-吲哚甲醛 、 3-溴苄溴 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以66%的产率得到1-(3-bromobenzyl)-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

• 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.
• 槐定碱吡咯、吲哚类衍生物及其制备方法与应 用
  申请人：广西大学

  公开号：CN108358923B

  公开（公告）日：2020-11-03

  一种槐定碱吡咯、吲哚类衍生物，本发明公开了该类化合物的化学结构，还公开了该类化合物的制备方法。本通过在体外抗肿瘤活性研究说明该类化合物具有发展前景的抗肿瘤药物，给广大的癌症患者提供多一种治疗的可能。