6β-propoxycholestane-3β,5α-diol | 106057-90-3

• 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: 6β-propoxycholestane-3β,5α-diol
• 英文别名: 6beta-n-Propoxy-3beta,5alpha-dihydroxycholestane；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-6-propoxy-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5-diol
• CAS: 106057-90-3
• 化学式: C₃₀H₅₄O₃
• 分子量: 462.757
• InChiKey: APEQFKQVSUJIDJ-HXVNYJTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5α-hydroxy-6β-propoxycholestan-3β-yl acetate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以95%的产率得到6β-propoxycholestane-3β,5α-diol
  参考文献：
  名称：

  Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR

  摘要：

  Chemically diverse oxysterols were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against seven cancer (HT-29, HepG2, A549, PC3, LAMA-84, MCF-7, and SH-SYSY) and two noncancerous cell lines (ARPE-19 and BJ). The influence of the oxidation pattern on rings A and B was studied. Oxygen functionalities on ring B, such as oxo, oxime, acetamide, acetate, and alkoxy, were evaluated. Most oxysterols were cytotoxic in the low micromolar range, with emphasis to the tetrols 14 and 34, the 6 beta methoxy and acetoxy derivatives 21 and 45, and the oxime 28. In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified. The cytotoxicity of 3 beta-acetates was lower than that of the parent alcohols, although incubation for a longer period rendered them equally cytotoxic, pointing them as potential prodrugs of oxysterols.

  DOI：

  10.1021/jm200803d

文献信息

• Method for the immunoanalysis of cholesterol epoxides
  申请人：——

  公开号：US04639420A1

  公开（公告）日：1987-01-27

  An immunoassay is provided for cholesterol epoxide. To prepare the antibodies used in the immunoassay, novel immunogens, are prepared which comprise a 3,5(6)-transdiaxial-dihydroxycholestane-6(5)-yl-hapten adduct linked to a covalently bonded bridge to a carrier protein. To detect cholesterol epoxide in the sample, it is converted to the hapten adduct, then contacted with the selected antibody.

  提供了一种胆固醇环氧化物的免疫测定方法。为了制备用于免疫测定的抗体，制备了新型免疫原，其包括一个3,5(6)-转二轴-二羟基胆甾烷-6(5)-基半抗原加合物，与一个共价键连接的载体蛋白。为了检测样品中的胆固醇环氧化物，将其转化为半抗原加合物，然后与选择的抗体接触。
• US4639420A
  申请人：——

  公开号：US4639420A

  公开（公告）日：1987-01-27
• Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm200803d

  日期：2011.9.22

  Chemically diverse oxysterols were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against seven cancer (HT-29, HepG2, A549, PC3, LAMA-84, MCF-7, and SH-SYSY) and two noncancerous cell lines (ARPE-19 and BJ). The influence of the oxidation pattern on rings A and B was studied. Oxygen functionalities on ring B, such as oxo, oxime, acetamide, acetate, and alkoxy, were evaluated. Most oxysterols were cytotoxic in the low micromolar range, with emphasis to the tetrols 14 and 34, the 6 beta methoxy and acetoxy derivatives 21 and 45, and the oxime 28. In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified. The cytotoxicity of 3 beta-acetates was lower than that of the parent alcohols, although incubation for a longer period rendered them equally cytotoxic, pointing them as potential prodrugs of oxysterols.