methyl 3,7,12-triacetoxycholan-24-oate | 6818-44-6

• 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: methyl 3,7,12-triacetoxycholan-24-oate
• 英文别名: 3α,7α,12α-trihydroxy-5β-cholanic acid 3,7,12-triacetate, methyl ester；methyl 3α,7α,12α-triacetyloxy-5β-cholan-24-oate；3α,7α,12α-Triacetoxy-5β-cholsaeuremethylester；methyl 3α,7α,12α-triacetoxy-5β-cholan-24-oate；3α,7α,12α-triacetoxy-5β-cholan-24-oic acid；methyl 3α,7α,12α-triacetoxycholanoate；Methyl triacetylcholate；methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-triacetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 6818-44-6
• 化学式: C₃₁H₄₈O₈
• 分子量: 548.717
• InChiKey: VTBGQCBIQJMJJZ-UJDSTXMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3,7,12-triacetoxycholan-24-oate 在 chromium(VI) oxide 、 甲醇 、 sodium hydroxide 、 硫酸 、 potassium carbonate 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  胆酸 在 吡啶 、 4-二甲氨基吡啶 、 三甲基硅烷化重氮甲烷 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 methyl 3,7,12-triacetoxycholan-24-oate
  参考文献：
  名称：

  利用利福平给药的食蟹猕猴鉴定胆汁酸3-O-硫酸盐结合物，作为有机阴离子转运多肽的潜在新型生物标志物。

  摘要：

  在寻找肝脏有机阴离子转运多肽（OATP）的新型胆汁酸（BA）生物标志物时，食蟹猕猴接受了四种剂量水平（1、3、10和30 mg / kg）的口服利福平（RIF），产生血浆无Cmax值（分别为0.06、0.66、2.57和7.79 µM），跨越了报告的OATP1B1和OATP1B3的体外IC50值（≤1.7μM）。如预期的那样，OATP探针药物（静脉注射2H4-匹伐他汀，0.2 mg / kg）的血浆浓度-时间曲线（AUC）下面积分别增加了1.2倍，2.4倍，3.8倍和4.5倍。对RIF食蟹猴的血浆进行液相色谱-串联质谱分析，该方法可支持30种不同BA的分析。对猴尿进行了分析，我们还确定了RIF对BA肾清除率的影响微乎其微。尽管硫酸化的BA仅占血浆BA池的1％，但观察到五个BA的硫酸盐具有强健的RIF剂量响应（血浆AUC的最大≥50倍增加）[糖去氧胆酸（GDCA-S），糖去氧胆酸（GCDCA-S

  DOI：

  10.1124/dmd.117.075275

文献信息

• Highly Powerful and Practical Acylation of Alcohols with Acid Anhydride Catalyzed by Bi(OTf)₃
  作者：Akihiro Orita、Chiaki Tanahashi、Atsushi Kakuda、Junzo Otera

  DOI：10.1021/jo0107453

  日期：2001.12.1

  Bi(OTf)(3)-catalyzed acylation of alcohols with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)(3)/acid anhydride protocol was so powerful that sterically demanding or tertiary alcohols could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technology was developed

  与其他酰化方法相比，评估了Bi（OTf）（3）催化的酸酐与酸酐的酰化反应。Bi（OTf）（3）/酸酐操作规程如此强大，以至于空间需求量高的或叔醇都可以被平滑地酰化。反应性较低的酰化试剂，例如苯甲酸酯和新戊酸酐，也可以通过这种催化活化。在这些情况下，为了克服将酰化产物与剩余的酰化试剂分离的困难，开发了一种新技术：未反应的酸酐的甲醇化成易于分离的甲酯实现了所需酰化产物的非常容易的分离。Bi（OTf）（3）/酸酐方案适用于具有各种功能的多种醇。酸不稳定的THP或TBS保护的醇，糠醇，香叶醇和碱不稳定的醇也可以被酰化。在室温下甚至进行官能化叔醇的酰化。
• A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane†
  作者：Takashi Iida、Takeru Yamaguchi、Ryusei Nakamori、Masahiro Hikosaka、Nariyasu Mano、Junichi Goto、Toshio Nambara

  DOI：10.1039/b104938k

  日期：——

  Oxyfunctionalization of unactivated methine carbon atoms with dimethyldioxirane (DMDO) is studied for various substituted steroids related to the 5β-cholane and 5α-cholestane series. A highly efficient, stereoselective, one-step remote oxidation of specific methine carbons is attained by DMDO oxidation under mild conditions to give a variety of novel mono- and dihydroxylated steroids. The reactivity and site selectivity

  研究了二甲基二环氧乙烷（DMDO）对未活化次甲基碳原子的氧官能化作用 类固醇 与5β-胆烷有关 5α-胆甾烷系列。高效，立体选择的一步式遥控器氧化作用 DMDO可实现特定的次甲基碳 氧化作用 在温和的条件下产生各种新颖的单羟基和二羟基 类固醇。远程氧官能化的反应性和位点选择性受结构和空间环境以及分子中目标次甲基碳原子的电子密度程度的影响。非酶促方法可有效地应用于生物活性物质的有效和短步合成类固醇。
• Osmiumporphyrin-Catalyzed Oxyfunctionalization and Isomerization of Natural (5β)-Bile Acids withtert-Butyl Hydroperoxide
  作者：Shoujiro Ogawa、Keiji Hosoi、Takashi Iida、Yasuo Wakatsuki、Mitsuko Makino、Yasuo Fujimoto、Alan F. Hofmann

  DOI：10.1002/ejoc.200700158

  日期：2007.7

  tert-Butyl hydroperoxide catalyzed by (meso-5,10,15,20-tetramesitylporphyrinate)osmium(II) carbonyl [Os(TMP)CO] was shown to be an efficient, versatile oxyfunctionalization system for the methyl ester peracetate derivatives of a series of common, natural (5β)-bile acids. Hydroxylation at C-5 and C-14, ketonization at C-15 and C-16, and isomerization at C-5 and C-14 in the nucleus were all attained

  由 (meso-5,10,15,20-tetramesitylporphyrinate) 锇 (II) 羰基 [Os(TMP)CO] 催化的叔丁基过氧化氢被证明是用于一系列过乙酸甲酯衍生物的高效、通用的氧官能化系统常见的天然 (5β)-胆汁酸。C-5和C-14的羟基化、C-15和C-16的酮化以及核内C-5和C-14的异构化均一步完成。讨论了控制区域选择性的因素以及这些化合物的形成机制。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis of steroidal cyclodimers from cholic acid; a molecular framework with potential for recognition and catalysis
  作者：Richard P. Bonar-Law、Anthony P. Davis

  DOI：10.1039/c39890001050

  日期：——

  Macrocycles (2a–f) were synthesized from cholic acid (1a) in up to 33% overall yield; the “cholaphane” framework on which they are based has substantial potential variability and should prove useful in biomimetic chemistry.

  大环化合物（2a – f）由胆酸（1a）合成，总收率高达33％；它们所基于的“胆碱”框架具有很大的潜在可变性，应该证明在仿生化学中很有用。
• Substituted 4-benzylaminoquinolines and their hetero analogs, process for their preparation, pharmaceuticals containing these compounds and use thereof
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06339077B1

  公开（公告）日：2002-01-15

  The invention relates to substituted 4-benzylaminoquinolines and their hetero analogs, and to the pharmaceutically acceptable salts and physiologically functional derivatives thereof. Compounds of formula I in which the radicals are defined in the specification, and their physiologically tolerated salts, physiologically functional derivatives and processes for their preparation are described. The compounds are suitable, for example, as medicines for the prophylaxis or treatment of gallstones.

  该发明涉及替代的4-苄基氨基喹啉及其杂环类似物，以及其药用可接受的盐和生理功能衍生物。描述了符合特定规范的式I化合物及其生理耐受盐、生理功能衍生物以及其制备方法。这些化合物可用作预防或治疗胆结石的药物。