2-(3,5-二苯基-1H-吡唑-1-基)-4-甲基噻唑-5-羧酸 | 1048363-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(3,5-二苯基-1H-吡唑-1-基)-4-甲基噻唑-5-羧酸
• 英文名称: 2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methylthiazole-5-carboxylic acid
• 英文别名: 2-(3,5-diphenylpyrazol-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid
• CAS: 1048363-86-5
• 化学式: C₂₀H₁₅N₃O₂S
• 分子量: 361.424
• InChiKey: AODKKWUXLUPDOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,5-二苯基-1H-吡唑-1-基)-4-甲基噻唑-5-羧酸 、 4-碘苄醇 在 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以65%的产率得到4-iodobenzyl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methylthiazole-5-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Antiviral Agents Targeting Flavivirus Envelope Proteins

  摘要：

  Flavivirus envelope proteins (E proteins) have been shown to play a pivotal role in virus assembly, morphogenesis, and infection of host cells. Inhibition of flavivirus infection of a host cell by means of a small molecule envelope protein antagonist is an attractive strategy for the development of antiviral agents. Virtual screening of the NCI chemical database using the dengue virus envelope protein structure revealed several hypothetical hit compounds. Bioassay results identified a class of thiazole compounds with antiviral potency in cell-based assays. Modification of these lead compounds led to a series of analogues with improved antiviral activity and decreased cytotoxicity. The most active compounds 11 and 36 were effective in the low micromolar concentration range in a cellular assay system.

  DOI：

  10.1021/jm800412d
• 作为产物：
  描述：

  ethyl 2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methylthiazole-5-carboxylate 在 lithium hydroxide 、 水 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到2-(3,5-二苯基-1H-吡唑-1-基)-4-甲基噻唑-5-羧酸
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Antiviral Agents Targeting Flavivirus Envelope Proteins

  摘要：

  Flavivirus envelope proteins (E proteins) have been shown to play a pivotal role in virus assembly, morphogenesis, and infection of host cells. Inhibition of flavivirus infection of a host cell by means of a small molecule envelope protein antagonist is an attractive strategy for the development of antiviral agents. Virtual screening of the NCI chemical database using the dengue virus envelope protein structure revealed several hypothetical hit compounds. Bioassay results identified a class of thiazole compounds with antiviral potency in cell-based assays. Modification of these lead compounds led to a series of analogues with improved antiviral activity and decreased cytotoxicity. The most active compounds 11 and 36 were effective in the low micromolar concentration range in a cellular assay system.

  DOI：

  10.1021/jm800412d

文献信息

• Design, Synthesis, and Biological Evaluation of Antiviral Agents Targeting Flavivirus Envelope Proteins
  作者：Ze Li、Mansoora Khaliq、Zhigang Zhou、Carol Beth Post、Richard J. Kuhn、Mark Cushman

  DOI：10.1021/jm800412d

  日期：2008.8.1

  Flavivirus envelope proteins (E proteins) have been shown to play a pivotal role in virus assembly, morphogenesis, and infection of host cells. Inhibition of flavivirus infection of a host cell by means of a small molecule envelope protein antagonist is an attractive strategy for the development of antiviral agents. Virtual screening of the NCI chemical database using the dengue virus envelope protein structure revealed several hypothetical hit compounds. Bioassay results identified a class of thiazole compounds with antiviral potency in cell-based assays. Modification of these lead compounds led to a series of analogues with improved antiviral activity and decreased cytotoxicity. The most active compounds 11 and 36 were effective in the low micromolar concentration range in a cellular assay system.