methyl 4,12-dioxy-3-aza-A-homo-7-deoxycholicate | 1313050-09-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: methyl 4,12-dioxy-3-aza-A-homo-7-deoxycholicate
• 英文别名: methyl (4R)-4-[(1S,2S,8R,11R,12S,15R,16R)-2,16-dimethyl-6,17-dioxo-5-azatetracyclo[9.7.0.02,8.012,16]octadecan-15-yl]pentanoate
• CAS: 1313050-09-7
• 化学式: C₂₅H₃₉NO₄
• 分子量: 417.589
• InChiKey: VYSGODNJXNISFF-ZJGGIWLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4,12-dioxy-3-aza-A-homo-7-deoxycholicate 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到methyl 4-oxy-12-hydroxyimino-3-aza-A-homo-deoxycholicate
  参考文献：
  名称：

  Synthesis and cytotoxicity of A-homo-lactam derivatives of cholic acid and 7-deoxycholic acid

  摘要：

  Using cholic acid and deoxycholic acid as starting materials, a series of 3-aza-A-homo-4-one bile acid and 7-deoxycholic acid derivatives were synthesized by the esterification, oxidation, reduction, oximation and Beckman rearrangement etc. The cytotoxicity of the synthesized compounds against MGC 7901 (human ventriculi carcinoma cell line), hela (human cervical carcinoma cell line), SMMC 7404 (human liver carcinoma cell line) were investigated. The results showed that bile acid and 7-deoxycholic-acid derivatives with 3-aza-A-homo-4-one configuration bearing a 6-hydroximino or 12-hydroximino group displayed a distinct cytotoxicity to Hela tumor cell line. In particular, the IC50 values of the compounds 6 and 13 were 14.3 and 24.3 mu mol/L against Hela human tumor cell line respectively. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.03.009
• 作为产物：
  描述：

  去氧胆酸 在 盐酸 、 氯化亚砜 、 盐酸羟胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl 4,12-dioxy-3-aza-A-homo-7-deoxycholicate
  参考文献：
  名称：

  Synthesis and cytotoxicity of A-homo-lactam derivatives of cholic acid and 7-deoxycholic acid

  摘要：

  Using cholic acid and deoxycholic acid as starting materials, a series of 3-aza-A-homo-4-one bile acid and 7-deoxycholic acid derivatives were synthesized by the esterification, oxidation, reduction, oximation and Beckman rearrangement etc. The cytotoxicity of the synthesized compounds against MGC 7901 (human ventriculi carcinoma cell line), hela (human cervical carcinoma cell line), SMMC 7404 (human liver carcinoma cell line) were investigated. The results showed that bile acid and 7-deoxycholic-acid derivatives with 3-aza-A-homo-4-one configuration bearing a 6-hydroximino or 12-hydroximino group displayed a distinct cytotoxicity to Hela tumor cell line. In particular, the IC50 values of the compounds 6 and 13 were 14.3 and 24.3 mu mol/L against Hela human tumor cell line respectively. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.03.009