1-[2-(4-羟基苯基)乙基]-3-(1,3-噻唑-2-基)硫脲 | 149485-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1-[2-(4-羟基苯基)乙基]-3-(1,3-噻唑-2-基)硫脲
• 英文名称: Thiourea, N-[2-(4-hydroxyphenyl)ethyl]-N'-2-thiazolyl-
• 英文别名: 1-[2-(4-hydroxyphenyl)ethyl]-3-(1,3-thiazol-2-yl)thiourea
• CAS: 149485-81-4
• 化学式: C₁₂H₁₃N₃OS₂
• 分子量: 279.387
• InChiKey: UJKOTIRUWXKVLY-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  467.7±47.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯乙胺 、 N-(thiazol-2-yl)-1H-imidazole-1-carbothioamide 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-[2-(4-羟基苯基)乙基]-3-(1,3-噻唑-2-基)硫脲
  参考文献：
  名称：

  Substituted heterocyclic thiourea compounds as a new class of anti-allergic agents inhibiting IgE/FcεRI receptor mediated mast cell leukotriene release

  摘要：

  Mast cell derived leukotrienes (LT's) play a vital role in pathophysiology of allergy and asthma. We synthesized various analogues of indolyl, naphthyl and phenylethyl substituted halopyridyl, thiazolyl and benzothiazolyl thioureas and examined their in vitro effects on the high affinity IgE receptor/FcepsilonRI-mediated mast cell leukotriene release. Of the 22 naphthylethyl thiourea compounds tested, there were 7 active compounds and N-[1-(1-naphthyl)ethyl]-N'-[2-(ethyl-4-acetylthiazolyl)]thiourea (17 and 16) (IC50=0.002 muM) and N-[1-(1R)-naphthylethyl]-N'-[2-(5-methylpyridyl)]thiourea (compound 5) (IC50 = 0.005 muM) were identified as the lead compounds. Among the 1l indolylethyl thiourea compounds tested, there were seven active compounds and the halopyridyl compounds N-[2-(3-indolylethyl)]-N'-[2-(5-chloropyridyl)lthiourea (24) and N-[2-(3-indolylethyl)]-N'-[2-(5-bromopyridyl)]thiourea (25) were the most active agents and inhibited the LTC4 release with low micromolar IC50 values of 4.9 and 6.1 PM, respectively. The hydroxylphenyl substituted compounds N-[2-(4-hydroxyphenyl)ethyl]-N'-[2-(5-chloropyridyl)]thiourea (37; IC50 = 12.6muM), N-[2-(4-hydroxyphenyl)ethyll-AT-[2-(5-bromopyridyl)]thiourea (50; IC50 16.8 muM) and N-[2-(4-hydroxyphenyl)ethyl]-N'-[2-(pyridyl)]thiourea (35; IC50 = 8.5muM) were the most active pyridyl thiourea agents. Notably, the introduction of electron withdrawing or donating groups had a marked impact on the biological activity of these thiourea derivatives and the Hammett sigma values of their substituents were identified as predictors of their potency. In contrast, experimentally determined partition coefficient values did not correlate with the biological activity of the thiourea compounds which demonstrates that their liphophilicity is not an important factor controlling their mast cell inhibitory effects. These results establish the substituted halopyridyl, indolyl and naphthyl thiourea compounds as a new chemical class of anti-allergic agents inhibiting IgE receptor/FcepsilonRI-mediated mast cell LTC4 release. Further lead optimization efforts may provide the basis for new and effective treatment as well as prevention programs for allergic asthma in clinical settings. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00531-x

文献信息

• [EN] AROMATIC AND HETEROCYCLIC THIAZOLYL THIOUREA COMPOUNDS AND USE<br/>[FR] COMPOSES DE THIAZOLYL THIOUREE AROMATIQUES ET HETEROCYCLIQUES ET UTILISATION
  申请人：PARKER HUGHES INST

  公开号：WO2002032889A1

  公开（公告）日：2002-04-25

  Novel aromatic and heterocyclic thiazolyl thiourea compounds, of the formula I and II and pharmaceutical compositions including such, and methods for their use are disclosed. The compounds are effective agents for the treatment of HIV infection, including non-nucleoside inhibitor-resistant, and multi-drug resistant strains of HIV.

  本发明涉及一种新型芳香族和杂环噻唑硫脲化合物，其化学式为I和II，以及包括这些化合物的制药组合物和使用它们的方法。这些化合物是治疗艾滋病毒感染的有效药物，包括非核苷类抑制剂耐药和多药耐药株的治疗剂。
• 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.
• AROMATIC AND HETEROCYCLIC THIAZOLYL THIOUREA COMPOUNDS AND USE
  申请人：Parker Hughes Institute

  公开号：EP1326852A1

  公开（公告）日：2003-07-16
• Aromatic and heterocyclic thiazolyl thiourea compounds and use
  申请人：Parker Hughes Institute

  公开号：US20030207921A1

  公开（公告）日：2003-11-06

  Novel aromatic and heterocyclic thiazolyl thiourea compounds, pharameutical compositions including such, and methods for their use are disclosed. The compounds are effective agents for the treatment of HIV infection, including non-nucleoside inhibitor-resistant, and multi-drug resistant strains of HIV.
• US6960606B2
  申请人：——

  公开号：US6960606B2

  公开（公告）日：2005-11-01