N'-(5-bromo-2-pyridyl)-N-[2-(2,5-dimethoxyphenyl)ethyl]thiourea | 233271-65-3

• 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: N'-(5-bromo-2-pyridyl)-N-[2-(2,5-dimethoxyphenyl)ethyl]thiourea
• 英文别名: N-[2-(2,5-dimethoxyphenylethyl)]-N'-[2-(5-bromopyridyl)]-thiourea；1-(5-Bromopyridin-2-yl)-3-[2-(2,5-dimethoxyphenyl)ethyl]thiourea
• CAS: 233271-65-3
• 化学式: C₁₆H₁₈BrN₃O₂S
• 分子量: 396.308
• InChiKey: GNLVRKKIIIVZHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基苯乙胺 、 imidazole-1-carbothionic acid (5-bromopyridin-2-yl)amide 以 N,N-二甲基甲酰胺 为溶剂， 生成 N'-(5-bromo-2-pyridyl)-N-[2-(2,5-dimethoxyphenyl)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

• Dihydroalkoxybenzyloxopyrimidine (DABO) derivatives exhibiting spermicidal activity
  申请人：Parker Hughes Institute

  公开号：EP1557197A1

  公开（公告）日：2005-07-27

  Novel phenethyl-5-bromopyridylthiourea (PBT) and dihydroalkoxybenzyloxopyrimidine (DABO) derivatives exhibiting spermicidal activity as well as anti-viral activity. These novel compounds can be incorporated within contraceptive compositions to provide for spermicidal or sperm-immobilizing activity.

  新型苯乙基-5-溴吡啶硫脲（PBT）和二氢烷氧基苄氧基嘧啶（DABO）衍生物具有杀精活性和抗病毒活性。这些新型化合物可加入避孕药具中，以提供杀精或精子固定活性。
• Nonnucleoside inhibitors of reverse transcriptase, composite binding pocket and methods for use thereof
  申请人：Vig Rakesh

  公开号：US20050153995A1

  公开（公告）日：2005-07-14

  Novel compounds that are potent inhibitors of HIV reverse transcriptase (RT) are described in the invention. Thes novel compounds also inhibit replication of a retrovirus, such as human immunodeficiency virus-1 (HIV-1). The novel compounds of the invention include analogs and derivatives of phenethylthiazolylthiourea (PETT), of dihydroalkoxybenzyloxopyrimidine (DABO), and of 1-[( 2 -hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). The invention additionally provides a composite HIV reverse-transcriptase (RT) nonnucleoside inhibitor (NNI) binding pocket constructed from a composite of multiple NNI-RT complexes The composite RT-NNI binding pocket provides a unique and useful tool for designing and identifying novel, potent inhibitors of reverse transcriptase.

  本发明描述了对 HIV 逆转录酶（RT）具有强效抑制作用的新型化合物。这些新型化合物还能抑制逆转录病毒（如人类免疫缺陷病毒-1（HIV-1））的复制。本发明的新型化合物包括苯乙基噻唑基硫脲（PETT）、二氢烷氧基苄氧基嘧啶（DABO）和 1-[( 2 -羟乙氧甲基]-6-(苯硫基)胸腺嘧啶 (HEPT)。此外，本发明还提供了一种由多种 NNI-RT 复合物复合而成的复合 HIV 逆转录酶（RT）非核苷抑制剂（NNI）结合袋。这种复合 RT-NNI 结合袋为设计和鉴定新型、强效的逆转录酶抑制剂提供了一种独特而有用的工具。
• NONNUCLEOSIDE INHIBITORS OF REVERSE TRANSCRIPTASE FOR THE TREATMENT OF HIV-INFECTION
  申请人：Parker Hughes Institute

  公开号：EP1064263A2

  公开（公告）日：2001-01-03
• PHENETHYL-5-BROMOPYRIDYLTHIOUREA (PBT) AND DIHYDROALKOXYBENZYLOXOPYRIMIDINE (DABO) DERIVATIVES EXHIBITING SPERMICIDAL ACTIVITY
  申请人：Parker Hughes Institute

  公开号：EP1140848A2

  公开（公告）日：2001-10-10
• PHENETHYL-5-BROMOPYRIDYLTHIOUREA (PBT) DERIVATIVES EXHIBITING SPERMICIDAL ACTIVITY
  申请人：Parker Hughes Institute

  公开号：EP1140848B1

  公开（公告）日：2005-10-12