1-(3-羟基吡啶-2-基)-3-苯基脲 | 115542-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3-羟基吡啶-2-基)-3-苯基脲
• 英文名称: Urea, N-(3-hydroxy-2-pyridinyl)-N'-phenyl-
• 英文别名: 1-(3-hydroxypyridin-2-yl)-3-phenylurea
• CAS: 115542-00-2
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: MUTZXOUXSQXRGW-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  364.1±27.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-羟基吡啶-2-基)-3-苯基脲 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以47%的产率得到1-(3-Isopentyloxy-2-pyridyl)-3-phenyl-urea
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Novel Inhibitors of Human Cyclophilin A

  摘要：

  Cyclophilin A is involved in many cellular processes, including protein folding and intracellular transports. Because cyclophilin A has been shown to interact with HIV-1 gag proteins and to enhance the viral infectivity, nonimmunosuppressive cyclophilin A ligands may represent a new class of therapeutic agents against HIV. Here, we report a virtual screening using structure- and pharmacophore-based design to identify original nonpeptidic cyclophilin ligands. Following a lead identification of compounds 1 [1-(3-benzyloxypyridin-2-yl)-3-(3-chlorophenyl)urea] and 2 [1-(3-benzyloxypyridin-2-yl)-3-(3-trifluoromethylphenyl)urea] (IC50 = 0.3 mu M), a series of molecules were synthesized from a diarylurea scaffold and evaluated for their in vitro ability to inhibit the cis-trans isomerase activity of cyclophilin A. Molecular modifications provided several more potent compounds, in particular analogues 4d and 4i with IC50 of 14 and 20 nM, respectively. Then, we evaluated the effect of analogues 1 and 2 on HIV virion infectivity in both immortalized and primary cells. Both 1 and 2 reduced virion infectivity in the replication-defective one-round infection assay, but only 1 impaired wild-type HIV infection in human peripheral blood mononuclear cells.

  DOI：

  10.1021/jm050716a
• 作为产物：
  描述：

  2-氨基-3-苄氧基吡啶 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 1-(3-羟基吡啶-2-基)-3-苯基脲
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of Novel Inhibitors of Human Cyclophilin A

  摘要：

  Cyclophilin A is involved in many cellular processes, including protein folding and intracellular transports. Because cyclophilin A has been shown to interact with HIV-1 gag proteins and to enhance the viral infectivity, nonimmunosuppressive cyclophilin A ligands may represent a new class of therapeutic agents against HIV. Here, we report a virtual screening using structure- and pharmacophore-based design to identify original nonpeptidic cyclophilin ligands. Following a lead identification of compounds 1 [1-(3-benzyloxypyridin-2-yl)-3-(3-chlorophenyl)urea] and 2 [1-(3-benzyloxypyridin-2-yl)-3-(3-trifluoromethylphenyl)urea] (IC50 = 0.3 mu M), a series of molecules were synthesized from a diarylurea scaffold and evaluated for their in vitro ability to inhibit the cis-trans isomerase activity of cyclophilin A. Molecular modifications provided several more potent compounds, in particular analogues 4d and 4i with IC50 of 14 and 20 nM, respectively. Then, we evaluated the effect of analogues 1 and 2 on HIV virion infectivity in both immortalized and primary cells. Both 1 and 2 reduced virion infectivity in the replication-defective one-round infection assay, but only 1 impaired wild-type HIV infection in human peripheral blood mononuclear cells.

  DOI：

  10.1021/jm050716a

文献信息

• PESHAKOVA, L. S.;KALCHEVA, V. B., DOKL. BOLG. AN, 41,(1988) N 1, 39-42
  作者：PESHAKOVA, L. S.、KALCHEVA, V. B.

  DOI：——

  日期：——
• N,N'-Diarylurea Compounds and N,N'-Diarylthiourea Compounds as Inhibitors of Translation Initiation
  申请人：President and Fellows of Harvard College

  公开号：US20160318857A1

  公开（公告）日：2016-11-03

  Compositions and methods for inhibiting translation initiation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using N,N′-diarylureas and/or N,N′-diarylthiourea compounds are described.
• US9932300B2
  申请人：——

  公开号：US9932300B2

  公开（公告）日：2018-04-03
• Structure-Based Design, Synthesis, and Biological Evaluation of Novel Inhibitors of Human Cyclophilin A
  作者：Jean-François Guichou、Julien Viaud、Clément Mettling、Guy Subra、Yea-Lih Lin、Alain Chavanieu

  DOI：10.1021/jm050716a

  日期：2006.2.1

  Cyclophilin A is involved in many cellular processes, including protein folding and intracellular transports. Because cyclophilin A has been shown to interact with HIV-1 gag proteins and to enhance the viral infectivity, nonimmunosuppressive cyclophilin A ligands may represent a new class of therapeutic agents against HIV. Here, we report a virtual screening using structure- and pharmacophore-based design to identify original nonpeptidic cyclophilin ligands. Following a lead identification of compounds 1 [1-(3-benzyloxypyridin-2-yl)-3-(3-chlorophenyl)urea] and 2 [1-(3-benzyloxypyridin-2-yl)-3-(3-trifluoromethylphenyl)urea] (IC50 = 0.3 mu M), a series of molecules were synthesized from a diarylurea scaffold and evaluated for their in vitro ability to inhibit the cis-trans isomerase activity of cyclophilin A. Molecular modifications provided several more potent compounds, in particular analogues 4d and 4i with IC50 of 14 and 20 nM, respectively. Then, we evaluated the effect of analogues 1 and 2 on HIV virion infectivity in both immortalized and primary cells. Both 1 and 2 reduced virion infectivity in the replication-defective one-round infection assay, but only 1 impaired wild-type HIV infection in human peripheral blood mononuclear cells.