5-(3-methyl-4-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole | 380922-09-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-methyl-4-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole
• CAS: 380922-09-8
• 化学式: C₁₉H₁₉N₃O₅
• 分子量: 369.377
• InChiKey: BPXREQVXVWBMIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-(3-methyl-4-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole 在 10percent Pd/C 氢气 作用下， 以 乙醇 为溶剂， 生成 5-(3-methyl-4-aminophenyl)-1-acetyl-3-(3,4,5-trimethoxyphenyl)-Δ1,5-pyrazoline 、 1-[3-(4-Amino-3-methylphenyl)-5-(3,4,5-trimethoxyphenyl)pyrazol-1-yl]ethanone
  参考文献：
  名称：

  New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models

  摘要：

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.

  DOI：

  10.1021/jm010231w
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 一水合肼 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-(3-methyl-4-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  New Antimitotic Agents with Activity in Multi-Drug-Resistant Cell Lines and in Vivo Efficacy in Murine Tumor Models

  摘要：

  During a screen for compounds that could inhibit cell proliferation, a series of new tubulin-binding compounds was identified with the discovery of oxadiazoline 1 (A-105972). This compound showed good cytotoxic activity against non-multi-drug-resistant and multi-drug-resistant cancer cell lines, but its utility in vivo was limited by a short half-life. Medicinal chemistry efforts led to the discovery of indolyloxazoline 22g (A-259745), which maintained all of the in vitro activity seen with oxadiazoline 1, but also demonstrated a better pharmacokinetic profile, and dose-dependent in vivo activity. Over a 28 day study, indolyloxazoline 22g increased the life span of tumor-implanted mice by up to a factor of 3 upon oral dosing. This compound, and others of its structural class, may prove to be useful in the development of new chemotherapeutic agents to treat human cancers.

  DOI：

  10.1021/jm010231w