1-(5-Bromo-pyridin-2-yl)-3-(2-p-tolyl-ethyl)-thiourea | 284040-61-5

• 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: 1-(5-Bromo-pyridin-2-yl)-3-(2-p-tolyl-ethyl)-thiourea
• 英文别名: 3X8QW8Msr7；1-(5-bromopyridin-2-yl)-3-[2-(4-methylphenyl)ethyl]thiourea
• CAS: 284040-61-5
• 化学式: C₁₅H₁₆BrN₃S
• 分子量: 350.282
• InChiKey: YDPLOGCASGLRQO-UHFFFAOYSA-N

物化性质

• 沸点：
  454.3±55.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  对甲基苯乙胺 、 imidazole-1-carbothionic acid (5-bromopyridin-2-yl)amide 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(5-Bromo-pyridin-2-yl)-3-(2-p-tolyl-ethyl)-thiourea
  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

• Phenethyl-thiourea compounds and use
  申请人：Parker Hughes Institute

  公开号：US20010003748A1

  公开（公告）日：2001-06-14

  Novel phenylethyl-thiourea (PHET) compounds as inhibitors of reverse transcriptase and effective agents for the treatment of HIV infection, including mutant, drug-sensitive, drug-resistant, and multi-drug resistant strains of HIV.

  新型苯乙基硫脲（PHET）化合物作为逆转录酶抑制剂和治疗艾滋病病毒感染的有效药物，包括艾滋病病毒的变异株、药物敏感株、耐药株和多重耐药株。
• PHENETYL-THIOUREA COMPOUNDS FOR TREATING HIV INFECTIONS
  申请人：Parker Hughes Institute

  公开号：EP1194406A1

  公开（公告）日：2002-04-10
• US6207688B1
  申请人：——

  公开号：US6207688B1

  公开（公告）日：2001-03-27
• US6362228B2
  申请人：——

  公开号：US6362228B2

  公开（公告）日：2002-03-26
• US6407246B2
  申请人：——

  公开号：US6407246B2

  公开（公告）日：2002-06-18