Thiourea, N-(2-phenylethyl)-N'-2-pyridinyl- | 5454-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: Thiourea, N-(2-phenylethyl)-N'-2-pyridinyl-
• 英文别名: 1-(2-phenylethyl)-3-pyridin-2-ylthiourea
• CAS: 5454-38-6
• 化学式: C₁₄H₁₅N₃S
• mdl: MFCD02754282
• 分子量: 257.359
• InChiKey: GVKFCKWGWXJWMN-UHFFFAOYSA-N

物化性质

• 沸点：
  413.3±47.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 2-苯基乙基异硫代氰酸酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 Thiourea, N-(2-phenylethyl)-N'-2-pyridinyl-
  参考文献：
  名称：

  苯乙基噻唑硫脲（PETT）化合物，一类新的HIV-1逆转录酶抑制剂。1. PETT类似物的合成及其基本的构效关系研究。

  摘要：

  描述了一系列新的有效的特异性HIV-1抑制化合物。该系列中的主要化合物N-（2-苯乙基）-N'-（2-噻唑基）硫脲（1）使用rCdG作为模板抑制HIV-1 RT，IC50为0.9 microM。在MT-4细胞中，化合物1抑制HIV-1的ED50为1.3 microM。细胞培养物中50％的细胞毒性剂量> 380 microM。通过将铅化合物概念上划分为四个象限来建立化学结构-活性关系（SAR）。搜救战略分为两个阶段。第一阶段涉及通过象限1-4的独立变化来优化抗病毒活性。第二阶段涉及制备结合了这些取代基中最好的杂化结构。进一步的SAR研究和药代动力学考虑导致鉴定N-（2-吡啶基）-N' -（5-溴-2-吡啶基）-硫脲（62; LY300046.HCl）可作为临床评估的候选药物。LY300046.HCl抑制HIV-1 RT的IC50为15 nM，在细胞培养中的ED50为20 nM。

  DOI：

  10.1021/jm00025a010

文献信息

• Compounds and methods for inhibition of HIV and related viruses
  申请人：Medivir Aktiebolag

  公开号：EP0540143A2

  公开（公告）日：1993-05-05

  Treatment of Aids, inhibition of the replication of HIV and related viruses, and formulations using thiourea derivative compounds or salts thereof are disclosed. Also disclosed are novel thiourea compounds.

  公开了治疗艾滋病、抑制 HIV 和相关病毒复制以及使用硫脲衍生物化合物或其盐的制剂。还公开了新型硫脲化合物。
• Substituted heterocyclic thiourea compounds as a new class of anti-allergic agents inhibiting IgE/FcεRI receptor mediated mast cell leukotriene release
  作者：T.K Venkatachalam、S Qazi、P Samuel、F.M Uckun

  DOI：10.1016/s0968-0896(02)00531-x

  日期：2003.3

  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.
• US5593993A
  申请人：——

  公开号：US5593993A

  公开（公告）日：1997-01-14
• US5658907A
  申请人：——

  公开号：US5658907A

  公开（公告）日：1997-08-19
• US5714503A
  申请人：——

  公开号：US5714503A

  公开（公告）日：1998-02-03