t-butyl 3α,7α-dihydroxy-12α-trifluoroacetoxy-5β-cholan-24-oate | 130781-88-3

• 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: t-butyl 3α,7α-dihydroxy-12α-trifluoroacetoxy-5β-cholan-24-oate
• 英文别名: tert-butyl 3α,7α-dihydroxy-12α-trifluoroacetoxy-5β-cholan-24-oate；tert-butyl 3α,7α-dihydroxy-12α-trifluoroacetoxy-5β-cholate
• CAS: 130781-88-3
• 化学式: C₃₀H₄₇F₃O₆
• 分子量: 560.695
• InChiKey: QTZHNNKSEFPMRL-BLFUJFHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  39.0
• 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：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  t-butyl 3α,7α-dihydroxy-12α-trifluoroacetoxy-5β-cholan-24-oate 在 吡啶 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 t-butyl 3α-acetoxy-7α,12α-dihydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Bonar-Law, Richard P.; Davis, Anthony P.; Sanders, Jeremy K. M., Journal of the Chemical Society. Perkin transactions I, 1990, # 8, p. 2245 - 2250

  摘要：

  DOI：
• 作为产物：
  描述：

  3α,7α-dihydroxy-12α-trifluoroacetoxy-5β-cholan-24-oic acid 、 叔丁醇 反应 16.0h， 以9.42 g的产率得到t-butyl 3α,7α-dihydroxy-12α-trifluoroacetoxy-5β-cholan-24-oate
  参考文献：
  名称：

  Investigation of new acyloxy derivatives of cholic acid and their esters as drug absorption modifiers

  摘要：

  Skin penetration enhancers are used in the formulation of transdermal delivery systems for drugs that are otherwise not sufficiently skin-permeable. Intestinal absorption promoters/enhancers are used as excipients in oral formulations of poorly oral-bioavailable drugs. Series of fourteen acyloxy derivatives of 5 beta-cholic acid as potential drug absorption modifiers was generated by multistep synthesis. The synthesis of all newly prepared compounds is presented here. Structure confirmation of all generated compounds was accomplished by H-1 NMR, C-13 NMR, IR and MS spectroscopy methods. All the prepared compounds were analyzed using RP-TLC, and their lipophilicity (R-M) was determined. The hydrophobicity (log P) and solubility (logS) of the studied compounds were also calculated using two commercially available programs. All the target compounds were tested for their in vitro transdermal penetration activity and as potential intestinal absorption enhancers. The anti-proliferative activity of all the final compounds was also assessed against the human cancer cell lines: T-lymphoblastic leukemia cell line and the breast adenocarcinoma cell line. Their cytotoxicity was also evaluated against the normal human skin fibroblast cells. Two compounds showed anti-proliferative effect on cancer cells without affecting the growth of normal cells, which should be promising in potential development of new drugs. Most of the target compounds showed minimal anti-proliferative activity (IC50 > 37 mu M), indicating they would have low cytotoxicity when administered as chemical absorption modifiers. The relationships between the lipophilicity and the chemical structure of the studied compounds as well as the relationships between their chemical structure and enhancement effects are discussed in this article. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.04.014

文献信息

• The Design and Synthesis of New Steroidal Compounds as Potential Mimics of Taxoids
  作者：Fanny Roussi、Quoc Anh Ngo、Sylviane Thoret、Françoise Guéritte、Daniel Guénard

  DOI：10.1002/ejoc.200500203

  日期：2005.9

  Eight new steroidal compounds bearing the phenylisoserine and benzoate side-chains of docetaxel were synthesised as potential mimics of antitumour taxoids. They were readily obtained either from cholic acid or from 4-androstene-3,17-dione by a reductive Tsuji–Trost/reduction one-pot reaction. Two compounds showed an unexpected inhibitory activity of tubulin assembly. (© Wiley-VCH Verlag GmbH & Co.

  合成了八种带有多西紫杉醇的苯基异丝氨酸和苯甲酸酯侧链的新甾体化合物，作为抗肿瘤紫杉类的潜在模拟物。它们很容易从胆酸或 4-androstene-3,17-dione 中通过还原性 Tsuji-Trost/还原一锅反应获得。两种化合物显示出意想不到的微管蛋白组装抑制活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Bonar-Law, Richard P.; Sanders, Jeremy K. M., Journal of the Chemical Society. Perkin transactions I, 1995, # 24, p. 3085 - 3096
  作者：Bonar-Law, Richard P.、Sanders, Jeremy K. M.

  DOI：——

  日期：——