4β-bromo-3-oxo-5β-cholan-24-oic acid | 104825-76-5

• 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: 4β-bromo-3-oxo-5β-cholan-24-oic acid
• 英文别名: 4β-bromo-3-oxocholanic acid；4β-bromo-3-oxo-5β-cholanoic acid-(24)；4β-Brom-3-oxo-5β-cholansaeure-(24)；(4R)-4-[(4R,5S,8S,9S,10R,13R,14S,17R)-4-bromo-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 104825-76-5
• 化学式: C₂₄H₃₇BrO₃
• 分子量: 453.46
• InChiKey: XNTZTQJAAZNSGD-GHCWTRHXSA-N

物化性质

• 沸点：
  540.5±25.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4β-bromo-3-oxo-5β-cholan-24-oic acid 在 盐酸 、 lithium carbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.3h， 生成 methyl 3-acetoxy-2,5-choladienate
  参考文献：
  名称：

  Miyamoto, Katsuhito; Kubodera, Noboru; Murayama, Eigoro, Synthetic Communications, 1986, vol. 16, # 5, p. 513 - 522

  摘要：

  DOI：
• 作为产物：
  描述：

  石胆酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 4β-bromo-3-oxo-5β-cholan-24-oic acid
  参考文献：
  名称：

  Miyamoto, Katsuhito; Kubodera, Noboru; Murayama, Eigoro, Synthetic Communications, 1986, vol. 16, # 5, p. 513 - 522

  摘要：

  DOI：

文献信息

• Dane; Wang; Schulte, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1937, vol. 245, p. 80,86
  作者：Dane、Wang、Schulte

  DOI：——

  日期：——
• Synthesis and in vitro biological activity of 4α-(2-propenyl)-5α-cholest-24-en-3α-ol: A 24,25-dehydro analog of the hypocholesterolemic agent 4α-(2-propenyl)-5α-cholestan-3α-ol
  作者：H Lin

  DOI：10.1016/s0039-128x(98)00083-x

  日期：1999.3

  4 alpha-(2-Propenyl)-5 alpha-cholestan-3 alpha-ol (LY295427) was previously identified from a Chinese hamster ovary (CHO) cell-based low density lipoprotein receptor/luciferase (LDLR/Luc) assay to be a potent transcriptional activator of the LDL receptor promoter in the presence of 25-hydroxycholesterol. To investigate the effect of the 24,25-unsaturation in the D-ring side chain (desmosterol D-ring side chain) on antagonizing the repressing effect of 25-hydroxycholesterol, 4 alpha-(2-propenyl)-5 alpha-cholest-24-en-3 alpha-ol (17), a 24,25-dehydro analog of LY295427, was thus synthesized from lithocholic acid via the formation of 3 alpha-[[(1,1-dimethylethyl)dimethylsilyl] oxy]-4 alpha-(2-propenyl)-5 alpha-cholan-24-al (15). Test results showed that 17 had an EC30 value of 2.6 mu M, comparable to 2.9 mu m of LY295427, in the CHO cell-based LDLR/Luc assay in the presence of 25-hydroxycholesterol. Apparently, the built-in 24,25-unsaturation in the D-ring side chain of 17 had added little effect to antagonizing the repressing effect of 25-hydroxycholesterol. In the [1-C-14-acetate]cholesterol biosynthesis inhibition assay, 17 at 10 mu g/ml (23 mu M) has been shown to inhibit the cholesterol biosynthesis in CHO cells by 38% relative to the vehicle control; whereas LY295427 showed no inhibition in the same assay in our previous studies. In contrast to LY295427, the built-in 24,25-unsaturation in the D-ring side chain of 17 has conferred an inhibitory effect on cholesterol biosynthesis in CHO cells. In summary, the observed LDL receptor promoter activity of 17 is related to its ability to prevent 25-hydroxycholesterol from exerting the repressing effect via an undetermined mechanism and, in part, to inhibit the cholesterol biosynthesis. (C) 1999 Elsevier Science Inc. All rights reserved.
• KUBODEHRA, NOBORU;MURAYAMA, EHJGORO;MIYAMOTO, KATSUXITO
  作者：KUBODEHRA, NOBORU、MURAYAMA, EHJGORO、MIYAMOTO, KATSUXITO

  DOI：——

  日期：——