1-(4-chlorobenzyl)-indole-3-carbohydrazide | 941867-89-6

• 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-(4-chlorobenzyl)-indole-3-carbohydrazide
• 英文别名: 1-[(4-Chlorophenyl)methyl]indole-3-carbohydrazide；1-[(4-chlorophenyl)methyl]indole-3-carbohydrazide
• CAS: 941867-89-6
• 化学式: C₁₆H₁₄ClN₃O
• 分子量: 299.76
• InChiKey: RUCJNKYYKWBAJC-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 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：
  60
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯基丙醇水合物 、 1-(4-chlorobenzyl)-indole-3-carbohydrazide 以 乙腈 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Indolyl-α-keto-1,3,4-oxadiazoles: Synthesis, anti-cell proliferation activity, and inhibition of tubulin polymerization

  摘要：

  DOI：

  10.1016/j.bmcl.2021.127842
• 作为产物：
  描述：

  吲哚-3-甲酸乙酯 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.25h， 生成 1-(4-chlorobenzyl)-indole-3-carbohydrazide
  参考文献：
  名称：

  프로카스파제-3의 활성화제로서 신규한 (E)-N-아릴리덴-1-(4-클로로벤질)-1H-인돌-3-카보하이드라지드 및 이를 유효성분으로 포함하는 항암제 조성물

  摘要：

  这是关于一种新型(E)-N-芳基亚甲基-1-(4-氯苯基)-1H-吲哚-3-羧酰肼及其作为procaspase-3的激活剂，并包含其作为有效成分的抗癌剂组合物的发明。

  公开号：

  KR20210154279A

文献信息

• Design, synthesis, and evaluation of novel <i>N'</i>-substituted-1-(4-chlorobenzyl)-1<i>H</i>-indol-3-carbohydrazides as antitumor agents
  作者：Le Cong Huan、Duong Tien Anh、Pham-The Hai、Lai Duc Anh、Eun Jae Park、A Young Ji、Jong Soon Kang、Do Thi Mai Dung、Dao Thi Kim Oanh、Truong Thanh Tung、Dinh Thi Thanh Hai、Sang-Bae Han、Nguyen-Hai Nam

  DOI：10.1080/14756366.2020.1816997

  日期：2020.1.1

  In continuity of our search for novel anticancer agents acting as procaspase activators, we have designed and synthesised two series of (E)-N '-benzylidene-carbohydrazides (4a-m) and(Z)-N'-(2-oxoindolin-3-ylidene)carbohydrazides (5a-g) incorporating 1-(4-chlorobenzyl)-1H-indole core. Bioevaluation showed that the compounds, especially compounds in series4a-m, exhibited potent cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). Within series4a-m, compounds with 2-OH substituent (4g-i) exhibited very strong cytotoxicity in three human cancer cell lines assayed with IC(50)values in the range of 0.56-0.83 mu M. In particular, two compounds4dand4fbearing4-Cland 4-NO(2)substituents, respectively, were the most potent in term of cytotoxicity with IC(50)values of 0.011-0.001 mu M. In caspase activation assay, compounds4band4fwere found to activate caspase activity by 314.3 and 270.7% relative to PAC-1. This investigation has demonstrated the potential of these simple acetohydrazides, especially compounds4b,4d, and4f, as anticancer agents.
• A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents
  作者：Dalip Kumar、N. Maruthi Kumar、Brett Noel、Kavita Shah

  DOI：10.1016/j.ejmech.2012.06.047

  日期：2012.9

  A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.
• Indolyl-α-keto-1,3,4-oxadiazoles: Synthesis, anti-cell proliferation activity, and inhibition of tubulin polymerization
  作者：Mukund P. Tantak、Monika Malik、Linus Klingler、Zachary Olson、Anil Kumar、Rachna Sadana、Dalip Kumar

  DOI：10.1016/j.bmcl.2021.127842

  日期：2021.4
• 프로카스파제-3의 활성화제로서 신규한 (E)-N-아릴리덴-1-(4-클로로벤질)-1H-인돌-3-카보하이드라지드 및 이를 유효성분으로 포함하는 항암제 조성물
  申请人：Chungbuk National University Industry-Academic Cooperation Foundation 충북대학교 산학협력단(220040168226) BRN ▼301-82-16304

  公开号：KR20210154279A

  公开（公告）日：2021-12-21

  본 발명은 프로카스파제-3(procaspase-3)의 활성화제로서 신규한 (E)-N-아릴리덴-1-(4-클로로벤질)-1H-인돌-3-카보하이드라지드 및 이를 유효성분으로 포함하는 항암제 조성물에 관한 것이다.

  这是关于一种新型(E)-N-芳基亚甲基-1-(4-氯苯基)-1H-吲哚-3-羧酰肼及其作为procaspase-3的激活剂，并包含其作为有效成分的抗癌剂组合物的发明。