24-ethylcholest-22-en-3β,6β-diol | 323180-20-7

• 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: 24-ethylcholest-22-en-3β,6β-diol
• 英文别名: (3S,6R,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
• CAS: 323180-20-7
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: AGZGHRXJCRERNU-HHIBCHPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  24-ethylcholest-22-en-3β,6β-diol 在 triethylamine-sulfur trioxide complex 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到disodium 24-ethyl-3β,6β-dihydroxycholest-22-ene disulfate
  参考文献：
  名称：

  Synthesis and cytotoxic analysis of some disodium 3β,6β-dihydroxysterol disulfates

  摘要：

  Disodium 3 beta,6 beta-dihydroxy-5 alpha-cholestane disulfate (1) was synthesized in 4 steps with a high overall yield from cholesterol. First, cholesterol (4a) was converted to cholest-4-en-3,6-dione (5a) via oxidation with pyridinium chlorochromate (PCC) and then 5a was reduced by NaBH4 in the presence of NiCl2 to produce cholest-3 beta,6 beta-diol (6a). The reaction of 6a with the triethylamine-sulfur trioxide complex generated diammonium 3 beta,6 beta-dihydroxy-5 alpha-cholestane disulfate (7a) and the treatment of 7a by cation exchange resin 732 (sodium form)(Na+) yielded the target steroid 1. Disodium 24-ethyl-3 beta,6 beta-dihydroxycholest-22-ene disulfate (2) and disodium 24-ethyl-3 beta,6 beta-dihydroxycholestane disulfate (3) were synthesized using a similar method. The cytotoxicity of these compounds against Sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells was investigated. Our results indicate that presence of a cholesterol-type side chain at position 17 is necessary for their biological activity. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.08.006
• 作为产物：
  描述：

  24-ethylcholest-4,22-dien-3,6-dione 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 以72%的产率得到24-ethylcholest-22-en-3β,6β-diol
  参考文献：
  名称：

  Synthesis and cytotoxic analysis of some disodium 3β,6β-dihydroxysterol disulfates

  摘要：

  Disodium 3 beta,6 beta-dihydroxy-5 alpha-cholestane disulfate (1) was synthesized in 4 steps with a high overall yield from cholesterol. First, cholesterol (4a) was converted to cholest-4-en-3,6-dione (5a) via oxidation with pyridinium chlorochromate (PCC) and then 5a was reduced by NaBH4 in the presence of NiCl2 to produce cholest-3 beta,6 beta-diol (6a). The reaction of 6a with the triethylamine-sulfur trioxide complex generated diammonium 3 beta,6 beta-dihydroxy-5 alpha-cholestane disulfate (7a) and the treatment of 7a by cation exchange resin 732 (sodium form)(Na+) yielded the target steroid 1. Disodium 24-ethyl-3 beta,6 beta-dihydroxycholest-22-ene disulfate (2) and disodium 24-ethyl-3 beta,6 beta-dihydroxycholestane disulfate (3) were synthesized using a similar method. The cytotoxicity of these compounds against Sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells was investigated. Our results indicate that presence of a cholesterol-type side chain at position 17 is necessary for their biological activity. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.08.006

文献信息

• Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (II)
  作者：Jianguo Cui、Lei Fan、Yanmin Huang、Yi Xin、Aimin Zhou

  DOI：10.1016/j.steroids.2009.07.009

  日期：2009.11

  side chain at position 17 is required for the biological activity of the compounds as we previously confirmed, elimination of the 4,5-double bond augmented the cytotoxic activity for the steroidal oximes. In addition, the presence of a hydroxy on 3- or 6-position of the steroidal nucleus resulted in a remarkable increase of cytotoxic activity. Our findings present more evidence showing the relationship

  从海洋海绵中分离出的羟氨基甾类化合物表现出多种生物学功能，包括细胞毒性和抗病毒功能。在这项研究中，我们合成了一系列在环A或B上具有不同官能团且在位置17处具有不同侧链的氢氧甾类衍生物，并分析了这些化合物对sk-Hep-1，H-292，PC-的细胞毒性3和Hey-1B癌细胞。我们的研究结果表明，尽管如我们先前所确认的，化合物17的胆固醇活性侧链对于化合物的生物学活性是必需的，但4,5双键的消除增强了甾体肟的细胞毒活性。另外，甾体核的3-或6-位上羟基的存在导致细胞毒性活性的显着增加。