3β-(O)-acetoxychol-5-en-24-ol | 152801-09-7

• 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: 3β-(O)-acetoxychol-5-en-24-ol
• 英文别名: 3β-acetoxychol-5-en-24-ol；acetic acid-(24-hydroxy-cholen-(5)-yl-(3β)-ester)；(10R)-3c-Acetoxy-10r.13c-dimethyl-17c-((R)-4-hydroxy-1-methyl-butyl)-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren；Essigsaeure-(24-hydroxy-cholen-(5)-yl-(3β)-ester)
• CAS: 152801-09-7
• 化学式: C₂₆H₄₂O₃
• 分子量: 402.618
• InChiKey: FCTPQTHGTITVRE-ISLLTSAGSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  495.2±28.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-(O)-acetoxychol-5-en-24-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到3β-acetoxy-Δ⁵-cholenic aldehyde
  参考文献：
  名称：

  SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents

  摘要：

  There is an urgent need for the development of new drugs for the treatment of neglected tropical diseases such as human African trypanosomiasis, Chagas disease and leishmaniasis. Azasterols, have been shown to have activity against the parasites which cause these diseases. In this paper we report synthesis of new azasterols and subsequent analysis of the SAR. The chemistry focused on variations in the ester at the 3 beta-position of the sterol and the position of the nitrogen in the side chain. The data allowed us to derive preliminary pharmacophore models for the activity of the azasterols against the parasites which cause these diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.062
• 作为产物：
  描述：

  3β-acetoxy-5-cholenic acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到3β-(O)-acetoxychol-5-en-24-ol
  参考文献：
  名称：

  SAR studies on azasterols as potential anti-trypanosomal and anti-leishmanial agents

  摘要：

  There is an urgent need for the development of new drugs for the treatment of neglected tropical diseases such as human African trypanosomiasis, Chagas disease and leishmaniasis. Azasterols, have been shown to have activity against the parasites which cause these diseases. In this paper we report synthesis of new azasterols and subsequent analysis of the SAR. The chemistry focused on variations in the ester at the 3 beta-position of the sterol and the position of the nitrogen in the side chain. The data allowed us to derive preliminary pharmacophore models for the activity of the azasterols against the parasites which cause these diseases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.062

文献信息

• Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol
  作者：Makoto Okamoto、Masayasu Tabe、Takao Fujii、Toshio Tanaka

  DOI：10.1016/0957-4166(95)00073-x

  日期：1995.3

  The chiral beta-amino alcohols-catalyzed addition of diisopropylzinc to steroidal 24-aldehydes successfully provided 24(R)-hydroxycholesterols in good yields with high diastereoselectivities, which are synthetic intermediates of 1 alpha,24(R)-dihydroxyvitamin D-3 (1). alpha,beta-Unsaturated steroidal aldehydes were found to give the corresponding isopropylated adducts in much higher yields (up to 91%) than those of saturated steroidal aldehydes.
• Steroid Acids and their Transformation Products. III. Desulfurization of Thiol Esters of 3(β)-Hydroxy-5-cholenic and -bisnor-5-cholenic Acids¹
  作者：A. Vern McIntosh、Elizabeth M. Meinzer、Robert H. Levin

  DOI：10.1021/ja01189a036

  日期：1948.9
• DE889745
  申请人：——

  公开号：——

  公开（公告）日：——