3-isothiocyanato-5-(4-methylphenyl)thiophene | 1258958-15-4

• 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: 3-isothiocyanato-5-(4-methylphenyl)thiophene
• 英文别名: 4-isothiocyanato-2-(4-methylphenyl)thiophene；5-(4-methylphenyl)thiophene-3-isothiocyanate
• CAS: 1258958-15-4
• 化学式: C₁₂H₉NS₂
• 分子量: 231.342
• InChiKey: YFCIBRGFRARLGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  3-isothiocyanato-5-(4-methylphenyl)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 3-(4-methoxyphenyl)-2-[5-(4-methylphenyl)-3-thienylimino]-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-甲基苯基)噻吩-2-羧酸 在 草酸 、 碳酸氢钠 作用下， 以 丙醇 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 3-isothiocyanato-5-(4-methylphenyl)thiophene
  参考文献：
  名称：

  Datoussaid, Yazid; Kirsch, Gilbert; Othman, Adil A., South African Journal of Chemistry, 2012, vol. 65, p. 223 - 227

  摘要：

  DOI：

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 and antiproliferative studies of 5-aryl-2-(3-thienylamino)-1,3,4-thiadiazoles
  作者：Germain Revelant、Charlène Gadais、Véronique Mathieu、Gilbert Kirsch、Stéphanie Hesse

  DOI：10.1016/j.bmcl.2014.04.043

  日期：2014.6

  A series of 5-aryl-2-(3-thienylamino)-1,3,4-thiadiazoles 3a-m were synthesized in good yields in two steps starting from thiophen-3-isothiocyanates. Those compounds as well as the thiosemicarbazide intermediates 2a-m were screened for their antiproliferative activity against a panel of six cancer cell lines. Among them, two 5-aryl-2-(3-thienylamino)-1,3,4-thiadiazoles (3f and 3i) have shown very interesting results with IC50 < 10 mu M on three cell lines. (C) 2014 Elsevier Ltd. All rights reserved.