23-[(aminocarbonothioyl)hydrazono]-3-hydroxolean-12-en-28-oic acid | 1604045-36-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 23-[(aminocarbonothioyl)hydrazono]-3-hydroxolean-12-en-28-oic acid
• 英文别名: gypsogenin thiosemicarbazone
• CAS: 1604045-36-4
• 化学式: C₃₁H₄₉N₃O₃S
• 分子量: 543.814
• InChiKey: KNBAEKFPHHVJFK-YWWPBNLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  38.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  107.94
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  23-[(aminocarbonothioyl)hydrazono]-3-hydroxolean-12-en-28-oic acid 、 (E,E)-dichloroglyoxime 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以60%的产率得到gypsogenin thiosemicarbazone glyoxime
  参考文献：
  名称：

  Synthesis, characterization and in vitro anti-neoplastic activity of gypsogenin derivatives

  摘要：

  Gypsogenin (L-1; 3-hydroxy-23-oxoolean-12-en-28-oic acid), a natural saponin, was isolated from the boiling water extract of Gypsophila arrostii roots. In addition, the derivatives gypsogenin thiosemicarbazone (L-2; 23-[(aminocarbonothioyl)hydrazono]-3-hydroxolean-12-en-28-oic acid) and gypsogenin thiosemicarbazone glyoxime ((LH2)-H-3; (3 beta)-3-hydroxy-23-[({[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]amino}carbonothioyl)hydrazono] olean-12-en-28-oic acid) as well as the Cu(II) and Co(II) complexes of (LH2)-H-3 were prepared. The structures were established on NMR analysis (H-1, C-13 NMR, HMBC, HMQC, and NOESY), FT-IR and completed by analysis of LC/MS. Furthermore, the antiproliferative effects of the Co(II) and Cu(II) complexes of the gypsogenin derivatives were assayed in human promyelocytic leukemia (HL 60) cells. These complexes were found to be potent anticancer agents with concentrations that inhibited 50% of proliferation (IpC50) between 5 mu M and 40 mu M. Cell death was distinguished by HO/PI double staining. The Co(II) complex of (LH2)-H-3 has shown approximately %50 apoptotic effect at 10 mu M concentration. Paclitaxel has been used as positive control. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.12.001
• 作为产物：
  描述：

  (3β, 4α)-3-羟基-23-氧代齐墩果-12-烯-28-酸 、 氨基硫脲 以 甲醇 、 水 为溶剂， 反应 61.0h， 以73 mg的产率得到23-[(aminocarbonothioyl)hydrazono]-3-hydroxolean-12-en-28-oic acid
  参考文献：
  名称：

  Synthesis, characterization and in vitro anti-neoplastic activity of gypsogenin derivatives

  摘要：

  Gypsogenin (L-1; 3-hydroxy-23-oxoolean-12-en-28-oic acid), a natural saponin, was isolated from the boiling water extract of Gypsophila arrostii roots. In addition, the derivatives gypsogenin thiosemicarbazone (L-2; 23-[(aminocarbonothioyl)hydrazono]-3-hydroxolean-12-en-28-oic acid) and gypsogenin thiosemicarbazone glyoxime ((LH2)-H-3; (3 beta)-3-hydroxy-23-[({[(1Z,2E)-N-hydroxy-2-(hydroxyimino)ethanimidoyl]amino}carbonothioyl)hydrazono] olean-12-en-28-oic acid) as well as the Cu(II) and Co(II) complexes of (LH2)-H-3 were prepared. The structures were established on NMR analysis (H-1, C-13 NMR, HMBC, HMQC, and NOESY), FT-IR and completed by analysis of LC/MS. Furthermore, the antiproliferative effects of the Co(II) and Cu(II) complexes of the gypsogenin derivatives were assayed in human promyelocytic leukemia (HL 60) cells. These complexes were found to be potent anticancer agents with concentrations that inhibited 50% of proliferation (IpC50) between 5 mu M and 40 mu M. Cell death was distinguished by HO/PI double staining. The Co(II) complex of (LH2)-H-3 has shown approximately %50 apoptotic effect at 10 mu M concentration. Paclitaxel has been used as positive control. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.12.001