(5beta,7alpha,12alpha)-7,12-双(乙酰氧基)-3-酮基胆烷-24-酸 | 300386-87-2

• 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
• 中文名称: (5beta,7alpha,12alpha)-7,12-双(乙酰氧基)-3-酮基胆烷-24-酸
• 英文名称: 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oic acid
• 英文别名: 7α.12α-diacetoxy-3-oxo-5β-cholanoic acid-(24)；7α.12α-Diacetoxy-3-oxo-5β-cholansaeure-(24)；(5beta,7alpha,12alpha)-7,12-Bis(acetyloxy)-3-oxocholan-24-oic acid；(4R)-4-[(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-diacetyloxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 300386-87-2
• 化学式: C₂₈H₄₂O₇
• 分子量: 490.637
• InChiKey: FLCQKKOYDHTRKE-QXOKQOCVSA-N

物化性质

• 沸点：
  593.7±50.0 °C(Predicted)
• 密度：
  1.18

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5beta,7alpha,12alpha)-7,12-双(乙酰氧基)-3-酮基胆烷-24-酸 在 吡啶 、 盐酸 、 氢氧化钾 、 amalgamated zinc 、 乙醇 、 氢溴酸 、 溴 、 aluminum isopropoxide 、 溶剂黄146 、 异丙醇 、 铂 作用下， 生成 5beta-胆烷酸
  参考文献：
  名称：

  Matsumoto, Journal of Biochemistry, 1944, vol. 36, p. 183,189

  摘要：

  DOI：
• 作为产物：
  描述：

  胆酸甲酯 在 chromium(VI) oxide 、 甲醇 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 异丙醇 、 丙酮 为溶剂， 反应 2.08h， 生成 (5beta,7alpha,12alpha)-7,12-双(乙酰氧基)-3-酮基胆烷-24-酸
  参考文献：
  名称：

  Cholic Acid Derivatives as 1,2,4,5-Tetraoxane Carriers:  Structure and Antimalarial and Antiproliferative Activity

  摘要：

  Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be similar to 2 times as active as the trans against Plasmodium falciparum DG and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.

  DOI：

  10.1021/jm000952f

文献信息

• Über die partielle Oxydation des Cholsäuremethylesters. (Untersuchungen über Sterine, XXVI)
  作者：Satoru Kuwada、Syozo Morimoto

  DOI：10.1246/bcsj.17.147

  日期：1942.3
• Sihn, Journal of Biochemistry, 1938, vol. 27, p. 425,427
  作者：Sihn

  DOI：——

  日期：——
• Matsumoto, Journal of Biochemistry, 1944, vol. 36, p. 183,189
  作者：Matsumoto

  DOI：——

  日期：——
• Cholic Acid Derivatives as 1,2,4,5-Tetraoxane Carriers:  Structure and Antimalarial and Antiproliferative Activity
  作者：Dejan Opsenica、Gabriela Pocsfalvi、Zorica Juranić、Bernard Tinant、Jean-Paul Declercq、Dennis E. Kyle、Wilbur K. Milhous、Bogdan A. Šolaja

  DOI：10.1021/jm000952f

  日期：2000.8.1

  Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be similar to 2 times as active as the trans against Plasmodium falciparum DG and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PRA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.