3β-(2-aminoethoxy)-7α,12α-dihydroxy-5β-cholan-24-oic acid methylester | 135053-76-8

• 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-(2-aminoethoxy)-7α,12α-dihydroxy-5β-cholan-24-oic acid methylester
• 英文别名: methyl 3beta-(2-aminoethoxy)cholate；methyl (4R)-4-[(3S,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2-aminoethoxy)-7,12-dihydroxy-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: 135053-76-8
• 化学式: C₂₇H₄₇NO₅
• 分子量: 465.674
• InChiKey: UXDVMRALHSFYEG-RXUFXJRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  102.01
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3β-(2-aminoethoxy)-7α,12α-dihydroxy-5β-cholan-24-oic acid methylester 在 lithium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-4-((3S,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3-{2-[3-(4-{[Benzyl-(3-methanesulfonylamino-2-methyl-phenyl)-amino]-methyl}-phenyl)-propionylamino]-ethoxy}-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentaoic acid
  参考文献：
  名称：

  Bile acid conjugates of a nonsteroidal glucocorticoid receptor modulator

  摘要：

  Bile acid conjugates of a selective nonsteroidal glucocorticoid receptor modulator were prepared and evaluated. Potent GR binding conjugates that showed improved metabolic stability were discovered. However, cellular potency and pharmacokinetics were not substantially improved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.022
• 作为产物：
  描述：

  methyl (3β,5β,7α,12α)-7,12-dixydroxy-3-(2-hydroxyethoxy)cholan-24-oate 在 N-溴代丁二酰亚胺(NBS) 、 氨 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 3β-(2-aminoethoxy)-7α,12α-dihydroxy-5β-cholan-24-oic acid methylester
  参考文献：
  名称：

  Bile acid conjugates of a nonsteroidal glucocorticoid receptor modulator

  摘要：

  Bile acid conjugates of a selective nonsteroidal glucocorticoid receptor modulator were prepared and evaluated. Potent GR binding conjugates that showed improved metabolic stability were discovered. However, cellular potency and pharmacokinetics were not substantially improved. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.022

文献信息

• 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。
• Specific Inhibitors of Ileal Bile Acid Transport
  作者：Guenther Wess、Werner Kramer、Alfons Enhsen、Heiner Glombik、Karl-Heinz Baringhaus、Georg Boeger、Matthias Urmann、Klaus Bock、Horst Kleine

  DOI：10.1021/jm00033a001

  日期：1994.4
• Preparation of 3α- and 3β-(ω-aminoalkoxy)-7α,12α-dihydroxy-5β-cholanoic acid esters: Versatile shuttles for drug targeting
  作者：G. Wess、W. Kramer、A. Enhsen、H. Glombik、K.-H. Baringhaus、K. Bock、H. Kleine、W. Schmitt

  DOI：10.1016/0040-4039(93)89020-q

  日期：1993.1

  Simple methodology for the preparation of 3alpha- and 3beta-(omega-aminoalkoxy)-cholanoic acid esters 7, 9 11, 13 and 15 is described starting from readily available bile acid derivatives. Protecting groups are not required
• Synthesis of bile acid - drug conjugates: Potential drug - shuttles for liver specific targeting
  作者：G. Wess、W. Kramer、G. Schubert、A. Enhsen、K.-H. Baringhaus、H. Glombik、S. Müllner、K. Bock、H. Kleine、M. John、O. Neckermann、A. Hoffmann

  DOI：10.1016/0040-4039(93)89021-h

  日期：1993.1

  Cholic acid (1) has been coupled via omega-aminoalkoxy spacer at C-3 to chlorambucil (3), HR 780 (4) and oxaproline peptide (5). Drug conjugates 9, 11, 18 exhibit strong affinity to specific bile acid transport systems.
• Bile acid–oligodeoxynucleotide conjugates: synthesis and liver excretion in rats
  作者：Dieter Starke、Kerstin Lischka、Peter Pagels、Eugen Uhlmann、Werner Kramer、Günter Wess、Ernst Petzinger

  DOI：10.1016/s0960-894x(01)00048-8

  日期：2001.4

  The synthesis of bile acid-oligodeoxynucleotide conjugates via the 3-OH group of the bile acids is described. When used in vivo in rats, covalent conjugation of an oligodeoxynucleotide via a linker to cholic acid resulted in an increased biliary excretion of bile acid-oligodeoxynucleotide conjugates compared to unconjugated oligodeoxynucleotides. (C) 2001 Elsevier Science Ltd. All rights reserved.