1-(3-Fluoro-phenyl)-3-pyridin-2-ylmethyl-thiourea | 75160-55-3

• 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: 1-(3-Fluoro-phenyl)-3-pyridin-2-ylmethyl-thiourea
• 英文别名: 1-(3-Fluorophenyl)-3-(pyridin-2-ylmethyl)thiourea
• CAS: 75160-55-3
• 化学式: C₁₃H₁₂FN₃S
• 分子量: 261.323
• InChiKey: QWPQRTRZXNQTBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-Fluoro-phenyl)-3-pyridin-2-ylmethyl-thiourea 在 N-甲基吗啉 、 tin(II) chloride dihdyrate 、 sodium acetate 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 benzyl (2S)-2-((4-((Z)-2-((3-fluorophenyl)imino)-4-oxo-3-(pyridin-2-ylmethyl)thiazolidin-5-yl)phenyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Inhibitors of HCV NS5A: From Iminothiazolidinones to Symmetrical Stilbenes

  摘要：

  The iminothiazolidinone BMS-858 (2) was identified as a specific inhibitor of HCV replication in a genotype 1b replicon assay via a high-throughput screening campaign. A more potent analogue, BMS-824 (18), was used in resistance mapping studies, which revealed that inhibitory activity was related to disrupting the function of the HCV nonstructural protein 5A. Despite the development of coherent and interpretable SAIL, it was subsequently discovered that in DMSO 18 underwent an oxidation and structural rearrangement to afford the thiohydantoin 47, a compound with reduced HCV inhibitory activity. However, HPLC bioassay fractionation studies performed after incubation of 18 in assay media led to the identification of fractions containing a dimeric species 48 that exhibited potent antiviral activity. Excision of the key elements hypothesized to be responsible for antiviral activity based on SAR observations reduced 48 to a simplified, symmetrical, pharmacophore realized most effectively with the stilbene 55, a compound that demonstrated potent inhibition of HCV in a genotype 1b replicon with an EC50 = 86 pM.

  DOI：

  10.1021/ml1002647
• 作为产物：
  描述：

  2-氨甲基吡啶 、 异硫氰酸(3-氟苯)酯 以 苯 为溶剂， 反应 0.17h， 以88%的产率得到1-(3-Fluoro-phenyl)-3-pyridin-2-ylmethyl-thiourea
  参考文献：
  名称：

  Bourdais, J.; Omar, A.-Mohsen M. E., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 555 - 558

  摘要：

  DOI：

文献信息

• BOURDAIS J.; OMAR A.-M. M. E., J. HETEROCYCL. CHEM., 1980, 17, NO 3, 555-558
  作者：BOURDAIS J.、 OMAR A.-M. M. E.

  DOI：——

  日期：——
• US4112100A
  申请人：——

  公开号：US4112100A

  公开（公告）日：1978-09-05
• Inhibitors of HCV NS5A: From Iminothiazolidinones to Symmetrical Stilbenes
  作者：Jeffrey L. Romine、Denis R. St. Laurent、John E. Leet、Scott W. Martin、Michael H. Serrano-Wu、Fukang Yang、Min Gao、Donald R O’Boyle、Julie A. Lemm、Jin-Hua Sun、Peter T. Nower、Xiaohua (Stella) Huang、Milind S. Deshpande、Nicholas A. Meanwell、Lawrence B. Snyder

  DOI：10.1021/ml1002647

  日期：2011.3.10

  The iminothiazolidinone BMS-858 (2) was identified as a specific inhibitor of HCV replication in a genotype 1b replicon assay via a high-throughput screening campaign. A more potent analogue, BMS-824 (18), was used in resistance mapping studies, which revealed that inhibitory activity was related to disrupting the function of the HCV nonstructural protein 5A. Despite the development of coherent and interpretable SAIL, it was subsequently discovered that in DMSO 18 underwent an oxidation and structural rearrangement to afford the thiohydantoin 47, a compound with reduced HCV inhibitory activity. However, HPLC bioassay fractionation studies performed after incubation of 18 in assay media led to the identification of fractions containing a dimeric species 48 that exhibited potent antiviral activity. Excision of the key elements hypothesized to be responsible for antiviral activity based on SAR observations reduced 48 to a simplified, symmetrical, pharmacophore realized most effectively with the stilbene 55, a compound that demonstrated potent inhibition of HCV in a genotype 1b replicon with an EC50 = 86 pM.
• Bourdais, J.; Omar, A.-Mohsen M. E., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 555 - 558
  作者：Bourdais, J.、Omar, A.-Mohsen M. E.

  DOI：——

  日期：——