1-(2-Phenoxy-ethyl)-3-thiazol-2-yl-thiourea

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-Phenoxy-ethyl)-3-thiazol-2-yl-thiourea
• 英文别名: 1-(2-phenoxyethyl)-3-(1,3-thiazol-2-yl)thiourea
• 化学式: C₁₂H₁₃N₃OS₂
• 分子量: 279.387
• InChiKey: MJPUUVIJLSCJEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide 、 2-苯氧基乙胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以48%的产率得到1-(2-Phenoxy-ethyl)-3-thiazol-2-yl-thiourea
  参考文献：
  名称：

  Anti-HIV activity of aromatic and heterocyclic Thiazolyl Thiourea compounds

  摘要：

  Several thiazolyl thiourea derivatives were designed and synthesized as non-nucleoside inhibitors (NNRTI) of HIV-1 reverse transcriptase. Six lead compounds were identified that showed subnanomolar IC50 values for the inhibition of HIV replication, were minimally toxic to human peripheral blood mononuclear cells (PBMC) with CC50 values ranging from 28 to >100 muM, and showed remarkably high selectivity indices ranging from 28,000 to >100,000. The most promising compound was N-[1-(1-furoylmethyl)]-N'-[2-(thiazolyl)]thiourea (compound 6), which showed potency against two NNRTI-resistant HIV-1 isolates (A17 and A17 variant) at nanomolar to low micromolar concentrations, exhibited much greater potency against both wild-type as well as NNRTI-resistant HIV-1 than nevirapine, delavirdine, HI-443, and HI-244, was minimally toxic to PBMC, and had a selectivity index of >100,000. The potency and minimal cytotoxicity of these aromatic/heterocyclic thiourea compounds suggest that they may be potentially useful as anti-AIDS drugs. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00011-7

文献信息

• Anti-HIV activity of aromatic and heterocyclic Thiazolyl Thiourea compounds
  作者：T.K. Venkatachalam、Elise A. Sudbeck、Chen Mao、Fatih M. Uckun

  DOI：10.1016/s0960-894x(01)00011-7

  日期：2001.2

  Several thiazolyl thiourea derivatives were designed and synthesized as non-nucleoside inhibitors (NNRTI) of HIV-1 reverse transcriptase. Six lead compounds were identified that showed subnanomolar IC50 values for the inhibition of HIV replication, were minimally toxic to human peripheral blood mononuclear cells (PBMC) with CC50 values ranging from 28 to >100 muM, and showed remarkably high selectivity indices ranging from 28,000 to >100,000. The most promising compound was N-[1-(1-furoylmethyl)]-N'-[2-(thiazolyl)]thiourea (compound 6), which showed potency against two NNRTI-resistant HIV-1 isolates (A17 and A17 variant) at nanomolar to low micromolar concentrations, exhibited much greater potency against both wild-type as well as NNRTI-resistant HIV-1 than nevirapine, delavirdine, HI-443, and HI-244, was minimally toxic to PBMC, and had a selectivity index of >100,000. The potency and minimal cytotoxicity of these aromatic/heterocyclic thiourea compounds suggest that they may be potentially useful as anti-AIDS drugs. (C) 2001 Published by Elsevier Science Ltd.