5-(4-chlorophenyl)-3-thiopheneamine | 120428-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-chlorophenyl)-3-thiopheneamine
• 英文别名: 5-(4-Chlorophenyl)thiophen-3-amine
• CAS: 120428-62-8
• 化学式: C₁₀H₈ClNS
• 分子量: 209.699
• InChiKey: YOWXPMQHZCTXHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  401.8±35.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-3-thiopheneamine 在 sodium acetate 、 碳酸氢钠 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 2-[(5-(4-chlorophenyl)-3-thienyl)imino]-3-(4-methoxyphenyl)-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-heteroarylimino-1,3-thiazolidin-4-ones as potential anti-tumor agents

  摘要：

  A series of 35 heteroarylimino-1,3-thiazolidinones with three sites of functionalization were synthesized and their antiproliferative properties were studied. The in vitro screening by MTT assay was performed against five cancer cell lines (human colon cancer cell lines HT29, HCT116 and SW620 and breast cancer cell lines MCF7 and MDA-MB-231). It was observed that N3-substituted thiazolidinones had moderate activities whereas 5-benzylidene thiazolidinones showed promising activities. To investigate the mechanism of action, detailed biological studies of six selected compounds (those presenting the lower mitotic index) were carried out on the human colon cancer HT29 cell line. Cell cycle assay revealed that those compounds induced cell accumulation in G2/M and in subG0/G1 phases of cell cycle. Moreover, dissipation of mitochondria membrane potential was observed as well as redox changes in treated cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.053
• 作为产物：
  描述：

  3-氨基-5-(4-氯苯基)-2-噻吩甲酸 在 草酸 作用下， 以 异丙醇 为溶剂， 以97%的产率得到5-(4-chlorophenyl)-3-thiopheneamine
  参考文献：
  名称：

  Synthesis of Novel 2-Thienylimino-1,3-thiazolidin-4-ones

  摘要：

  本文介绍了用 3-氨基噻吩-2-羧酸酯通过简单的四步程序制备新的 2-噻吩亚氨基-1,3-噻唑烷-4-酮的方法。

  DOI：

  10.1055/s-0029-1218780

文献信息

• Synthesis of Novel N-Substituted 2-(Hetero)arylimino-1,3-thiazolidin-4-ones
  作者：Stéphanie Hesse、Germain Revelant、Gilbert Kirsch

  DOI：10.1055/s-0030-1257867

  日期：2010.10

  The preparation of new N-substituted 2-arylimino-1,3-thiazolidin-4-ones from 5-substituted-3-aminothiophenes using an easy three-step procedure is described. 5-substituted 3-aminothiophenes - isothiocyanates - thioureas - N-substituted 1,3-thiazolidin-4-ones

  描述了使用简单的三步程序从5个取代的3-氨基噻吩制备新的N-取代的2-limlinino-1,3-thiazolidin-4-ones。 5-取代的3-氨基噻吩-异硫氰酸酯-硫脲-N-取代的1,3-噻唑烷-4-酮
• Synthesis of Novel 2-Thienylimino-1,3-thiazolidin-4-ones
  作者：Gilbert Kirsch、Ismail Abdillahi、Germain Revelant、Yazid Datoussaid

  DOI：10.1055/s-0029-1218780

  日期：2010.8

  The preparation of new 2-thienylimino-1,3-thiazolidin-4-ones from 3-aminothiophene-2-carboxylate using an easy four-step procedure is described.

  本文介绍了用 3-氨基噻吩-2-羧酸酯通过简单的四步程序制备新的 2-噻吩亚氨基-1,3-噻唑烷-4-酮的方法。
• Substituted N-benzoyl-N'-thienyl ureas, and their use as insecticides
  申请人：SANDOZ AG

  公开号：EP0300972A1

  公开（公告）日：1989-01-25

  Substituted N-benzoyl-N′-thienyl-ureas, processes for their product­ion and their use in the control of pests.

  取代的 N-苯甲酰基-N′-噻吩基脲、其生产工艺及其在防治害虫中的应用。
• Synthesis and biological evaluation of novel 2-heteroarylimino-1,3-thiazolidin-4-ones as potential anti-tumor agents
  作者：Germain Revelant、Sophie Huber-Villaume、Sandrine Dunand、Gilbert Kirsch、Hervé Schohn、Stéphanie Hesse

  DOI：10.1016/j.ejmech.2015.02.053

  日期：2015.4

  A series of 35 heteroarylimino-1,3-thiazolidinones with three sites of functionalization were synthesized and their antiproliferative properties were studied. The in vitro screening by MTT assay was performed against five cancer cell lines (human colon cancer cell lines HT29, HCT116 and SW620 and breast cancer cell lines MCF7 and MDA-MB-231). It was observed that N3-substituted thiazolidinones had moderate activities whereas 5-benzylidene thiazolidinones showed promising activities. To investigate the mechanism of action, detailed biological studies of six selected compounds (those presenting the lower mitotic index) were carried out on the human colon cancer HT29 cell line. Cell cycle assay revealed that those compounds induced cell accumulation in G2/M and in subG0/G1 phases of cell cycle. Moreover, dissipation of mitochondria membrane potential was observed as well as redox changes in treated cells. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Datoussaid, Yazid; Kirsch, Gilbert; Othman, Adil A., South African Journal of Chemistry, 2012, vol. 65, p. 223 - 227
  作者：Datoussaid, Yazid、Kirsch, Gilbert、Othman, Adil A.、Abdillahi, Ismail

  DOI：——

  日期：——