cholest-4α-methyl-7-en-3β-ol hemisuccinate

• 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: cholest-4α-methyl-7-en-3β-ol hemisuccinate
• 英文别名: 4-oxo-4-[[(3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]butanoic acid
• 化学式: C₃₂H₅₂O₄
• 分子量: 500.762
• InChiKey: FUCYLMKQNGECJS-FXKHJSSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基胆甾-7-烯-3-醇 、 丁二酰氯 以 四氢呋喃 为溶剂， 反应 28.0h， 以61%的产率得到cholest-4α-methyl-7-en-3β-ol hemisuccinate
  参考文献：
  名称：

  Synthesis and antitumor activity of cholest-4α-methyl-7-en-3β-ol derivatives

  摘要：

  Cholest-4 alpha-methyl-7-en-3 beta-ol (1) has potent inhibitory activity against pc 12 tumor with 0.5043 ratio (10 mu g/mL). This paper describes a series of structural modification of this compound, which focus on 3 beta-hydroxyl group and 7(8)-double bond. The synthesized derivatives of I were tested for human cancer cell lines including colon cancer (HCT-8), liver cancer (BEL-7402) and nasopharyngeal cancer (KB) cells. The results showed that cholest-4 alpha-methyl-8-en-3 beta,7 alpha-diol 6a inhibits KB cell significantly with IC50 1.32 x 10(-9) mu g/ml. In addition, the cytotoxic properties of this compound against HCT-8 and BEL-7402 are excellent with IC50 1.2 mu g/mL. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.01.006

文献信息

• Synthesis and antitumor activity of cholest-4α-methyl-7-en-3β-ol derivatives
  作者：Lan He、Yumei Liu、Jiangong Shi、Qiang Pei

  DOI：10.1016/j.steroids.2006.01.006

  日期：2006.6

  Cholest-4 alpha-methyl-7-en-3 beta-ol (1) has potent inhibitory activity against pc 12 tumor with 0.5043 ratio (10 mu g/mL). This paper describes a series of structural modification of this compound, which focus on 3 beta-hydroxyl group and 7(8)-double bond. The synthesized derivatives of I were tested for human cancer cell lines including colon cancer (HCT-8), liver cancer (BEL-7402) and nasopharyngeal cancer (KB) cells. The results showed that cholest-4 alpha-methyl-8-en-3 beta,7 alpha-diol 6a inhibits KB cell significantly with IC50 1.32 x 10(-9) mu g/ml. In addition, the cytotoxic properties of this compound against HCT-8 and BEL-7402 are excellent with IC50 1.2 mu g/mL. (c) 2006 Elsevier Inc. All rights reserved.