N-[2-(2-fluorophenethyl)]-N'-[2-(5-bromo-pyridyl)]thiourea | 219664-37-6

• 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-[2-(2-fluorophenethyl)]-N'-[2-(5-bromo-pyridyl)]thiourea
• 英文别名: 1-(5-Bromopyridin-2-yl)-3-[2-(2-fluorophenyl)ethyl]thiourea
• CAS: 219664-37-6
• 化学式: C₁₄H₁₃BrFN₃S
• 分子量: 354.246
• InChiKey: MIJLSRZJDIBHJU-UHFFFAOYSA-N

物化性质

• 沸点：
  441.4±55.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氟苯乙胺 、 imidazole-1-carbothionic acid (5-bromopyridin-2-yl)amide 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以71%的产率得到N-[2-(2-fluorophenethyl)]-N'-[2-(5-bromo-pyridyl)]thiourea
  参考文献：
  名称：

  NNI for treatment of multi-drug resistant HIV

  摘要：

  本发明涉及用于治疗HIV感染的化合物和方法。

  公开号：

  US07186736B1

文献信息

• Gel-microemulsion formulations
  申请人：——

  公开号：US20030083314A1

  公开（公告）日：2003-05-01

  A pharmaceutical composition adapted for use as a spermicide, the composition comprising a gel-microemulsion comprising an oil-in-water microemulsion and a polymeric hydrogel. The gel-microemulsion can be used in a spermicidal method. Also, a gel-microemulsion pharmaceutical composition adapted for use as a formulation base for additional therapeutic agents. Examples of additional agents include, anti-microbial agents and spermicidal agents. Such gel-microemulsions with additional therapeutic agents can be used in methods for appropriate therapeutic treatment. Also, a gel-microemulsion pharmaceutical composition that is adapted for use as both a spermicide and formulation base for anti-microbial agents to provide a dual function contraceptive/anti-microbial formulation. Method of using such a composition as a dual function contraceptive/anti-microbial formulation are also included.

  一种适用于作为精子杀死剂的制药组合物，该组合物包括一种凝胶微乳液，其中包括一种油包水微乳液和一种聚合物水凝胶。该凝胶微乳液可用于精子杀死方法。此外，一种适用于作为附加治疗剂的配方基础的凝胶微乳液制药组合物。附加剂例子包括抗微生物剂和精子杀死剂。这种带有附加治疗剂的凝胶微乳液可以用于适当的治疗方法。此外，一种适用于作为既是精子杀死剂又是抗微生物剂配方基础的凝胶微乳液制药组合物，以提供双重功能避孕/抗微生物制剂。使用这种组合物作为双重功能避孕/抗微生物制剂的方法也包括在内。
• Nonnucleoside inhibitors of reverse transcriptase for the treatment of HIV infection
  申请人：Parker Hughes Institute

  公开号：EP1528057A1

  公开（公告）日：2005-05-04

  Novel compounds that are potent inhibitors of HIV reverse transcriptase (RT) are described in the invention. These novel compounds also inhibit replication of a retrovirus, such as human immunodeficiency virus-1 (HIV-I). The novel compounds of the invention include analogs and derivatives of phenethylthiazolylthiourea (PETT), of dihydroalkoxybenzy-loxopyrimidine (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-I））的复制。本发明的新型化合物包括苯乙基噻唑基硫脲（PETT）、二氢烷氧基苄基环嘧啶（DABO）和 1-[(2-羟基乙氧基)甲基]-6-(苯硫基)胸腺嘧啶（HEPT）的类似物和衍生物。本发明还提供了一种复合 HIV 逆转录酶（RT）非核苷抑制剂（NNI）结合袋，该结合袋由多个 NNI-RT 复合物复合而成。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独特而有用的工具。
• 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。
• Rational design and synthesis of phenethyl-5-bromopyridyl thiourea derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase
  作者：Rakesh Vig、Chen Mao、T.K Venkatachalam、Lisa Tuel-Ahlgren、Elise A Sudbeck、Fatih M Uckun

  DOI：10.1016/s0968-0896(98)00108-4

  日期：1998.10

  A series of novel phenethylthiazolylthiourea (PETT) derivatives targeting the nonnucleoside inhibitor (NNI) binding site of HIV reverse transcriptase (RT) have been designed based on the structure of the NNI binding pocket. The structure-based design and synthesis of these new PETT derivatives were complemented by biological assays of their anti-HIV activity. Modeling studies for rational drug design included the construction of a composite NNI binding pocket from nine RT-NNI crystal structures, the analyses of surface complementarity between NNI and RT, and application of K-i calculations combined with a docking procedure involving the novel PETT derivatives. The use of the composite NNI binding pocket allowed the identification and structure-based design of three promising PETT derivatives with ortho-F (2), ortho-Cl (3), and meta-F (5) substituents on the phenyl ring. These novel PETT derivatives were more active than AZT or trovirdine and showed potent anti-HIV activity with IC50[p24] values of <1 nM and selectivity indices of > 100,000. (C) 1998 Elsevier Science Ltd. All rights reserved.