4-isothiocyanato-2-(4-chlorophenyl)thiophene | 1258958-16-5

• 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: 4-isothiocyanato-2-(4-chlorophenyl)thiophene
• 英文别名: 5-(4-chlorophenyl)-3-isothiocyanatothiophene；2-(4-Chlorophenyl)-4-isothiocyanatothiophene
• CAS: 1258958-16-5
• 化学式: C₁₁H₆ClNS₂
• 分子量: 251.76
• InChiKey: SCMCZGBUYJFHOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-isothiocyanato-2-(4-chlorophenyl)thiophene 在 sodium acetate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 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：

  5-(4-chlorophenyl)-3-thiopheneamine 、 硫光气 在 碳酸氢钠 作用下， 以 氯仿 、 水 为溶剂， 以60%的产率得到4-isothiocyanato-2-(4-chlorophenyl)thiophene
  参考文献：
  名称：

  新型N-取代的2-（杂）芳基-1,3-噻唑烷酮-4-酮的合成

  摘要：

  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

  DOI：

  10.1055/s-0030-1257867

文献信息

• Synthesis of novel 2-aminothieno[3,2-d]thiazoles and selenolo[3,2-d]thiazoles
  作者：Germain Revelant、Stéphanie Hesse、Gilbert Kirsch

  DOI：10.1016/j.tet.2011.09.134

  日期：2011.12

  3-aminoselenophenes (using thiophosgene). Those compounds were then converted to the corresponding thioureas in the presence of ammonium hydroxide. Cyclization in 2-aminoselenolo[3,2-d]thiazoles was achieved using DDQ. 2-Aminothieno[3,2-d]thiazoles were obtained from 3-isothiocyanatothiophenes using the same pathway.

  在这项工作中，我们描述了从3-氨基硒吩（使用硫光气）开始的3-isothiocyanatoselenophenes的合成。然后在氢氧化铵存在下将那些化合物转化为相应的硫脲。使用DDQ在2-氨基硒代[3,2- d ]噻唑中环化。使用相同的途径从3-异硫氰酸根合噻吩获得2-氨基噻吩并[3,2- d ]噻唑。
• 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：——