2-amino-1-[5-[4-(dimethylamino)phenyl]-2-(3,4,5-trimethoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone | 380922-05-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-amino-1-[5-[4-(dimethylamino)phenyl]-2-(3,4,5-trimethoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone
• CAS: 380922-05-4
• 化学式: C₂₁H₂₆N₄O₅
• 分子量: 414.461
• InChiKey: CYHAIJISZIDAPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲酸 、 2-amino-1-[5-[4-(dimethylamino)phenyl]-2-(3,4,5-trimethoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以47%的产率得到N-[2-[5-[4-(dimethylamino)phenyl]-2-(3,4,5-trimethoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]-2-oxoethyl]formamide
  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：

  2-azido-1-[5-[4-(dimethylamino)phenyl]-2-(3,4,5-trimethoxyphenyl)-2H-1,3,4-oxadiazol-3-yl]ethanone 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以38%的产率得到2-amino-1-[5-[4-(dimethylamino)phenyl]-2-(3,4,5-trimethoxyphenyl)-2H-1,3,4-oxadiazol-3-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