1-(4-chlorobenzyl)-1H-indole-3-carbothioamide | 1338059-24-7

• 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-(4-chlorobenzyl)-1H-indole-3-carbothioamide
• 英文别名: 1-[(4-chlorophenyl)methyl]indole-3-carbothioamide
• CAS: 1338059-24-7
• 化学式: C₁₆H₁₃ClN₂S
• 分子量: 300.812
• InChiKey: CGCVAMBIXGZYRC-UHFFFAOYSA-N

物化性质

• 沸点：
  513.3±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 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：
  63
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzyl)-1H-indole-3-carbothioamide 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到3,5-Bis[1-[(4-chlorophenyl)methyl]indol-3-yl]-1,2,4-thiadiazole
  参考文献：
  名称：

  Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles

  摘要：

  A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.089
• 作为产物：
  描述：

  1-(4-氯苄基)-1H-吲哚-3-甲醛 在 sodium hydrogen sulfide 、 甲酸 、 magnesium(II) chloride hexahydrate 、 盐酸羟胺 、 sodium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-chlorobenzyl)-1H-indole-3-carbothioamide
  参考文献：
  名称：

  Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles

  摘要：

  A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.089

文献信息

• A green synthesis and antibacterial activity of ferrocene-based thiazole derivatives in choline chloride/glycerol eutectic solvent
  作者：Di Zhao、Yanying Liu、Yang Li、Yu Chen

  DOI：10.1039/d2ra04587g

  日期：——

  Subsequently, a preliminary screening for in vitro antibacterial activities of all these newly-synthesized compounds revealed that the halo-substituted (F, Cl, Br) compounds 3f–h showed significant antibacterial activities against Gram (+) bacterial B. subtilis and Gram (−) E. coli, among which the fluoro-substituted 3f possessed the best activity with the MIC value of 7.8125 μg mL−1, being higher

  本工作成功完成了4-二茂铁基噻唑衍生物的绿色Hantzsch合成。溴乙酰基二茂铁和各种芳基硫脲、1-烷基吲哚-3-或 9-烷基咔唑-3-硫代硫酰胺之间的 Hantzsch 反应在低共熔溶剂 (DES)（即氯化胆碱/甘油 (ChCl/Gly) (1:2)）中有效进行摩尔比）在80°C，避免使用常见的挥发性有机溶剂。此外，DES 介质最多可重复使用 3 次，且产量不会明显下降。该合成策略具有反应条件温和、环境友好、实验简单、后处理过程简单、收率高等优点。随后，对所有这些新合成的化合物的体外抗菌活性进行了初步筛选，结果表明，卤代（F、Cl、Br）化合物3f–h对革兰氏（+）细菌枯草芽孢杆菌和革兰氏（）表现出显着的抗菌活性。 −)大肠杆菌，其中氟代3f活性最好，MIC值为7.8125 μg mL -1 ，高于对照药环丙沙星（15.625 μg mL -1 ）。
• 2-(3′-Indolyl)-N-arylthiazole-4-carboxamides: Synthesis and evaluation of antibacterial and anticancer activities
  作者：Mukund P. Tantak、Jing Wang、Rajnish Prakash Singh、Anil Kumar、Kavita Shah、Dalip Kumar

  DOI：10.1016/j.bmcl.2015.07.105

  日期：2015.10

  A new series of 2-(3'-indolyl)-N-arylthiazole-4-carboxamides 17a-p has been designed and synthesized. Initial reaction of readily available thioamides 15 with bromopyruvic acid under refluxing conditions produced different thiazole carboxylic acids 16 which upon coupling with arylamines by using EDCI.HCl and HOBt afforded diverse arylthiazole-4-carboxamides 17a-p in 78-87% yields. Antibacterial activity evaluation against Gram-positive and Gram-negative bacterial strains led to compounds 17i-k and 17o as potent and selectively (Gram-negative) antibacterial agents. The cytotoxicity of thiazole carboxamides 17a-p was also evaluated on a panel of human cancer cell lines. Among the tested derivatives, compounds 17i (IC50 = 8.64 mu M; HEK293T) and 17l (IC50 = 3.41 mu M; HeLa) were identified as the most potent analogues of the series. Preliminary mechanism of action studies of thiazole carboxamide 17i suggested that its cytotoxicity against HeLa cells involves the induction of cell death by apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles
  作者：Dalip Kumar、N. Maruthi Kumar、Kuei-Hua Chang、Ritika Gupta、Kavita Shah

  DOI：10.1016/j.bmcl.2011.07.089

  日期：2011.10

  A series of 3,5-bis(indolyl)-1,2,4-thiadiazoles were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-thiocarboxamide 3 with iodobenzene diacetate underwent oxidative dimerization to give 3,5-bis(indolyl)-1,2,4-thiadiazoles 4a-n. Among the synthesized bis(indoly)-1,2,4-thiadiazoles, the compound 4h with 4-chlorobenzyl and methoxy substituents showed the most potent activity. (C) 2011 Elsevier Ltd. All rights reserved.