(3β,5β,7α,12α)-3-[(6-amino-1-oxohexyl)amino]-7,12-dihydroxycholan-24-oic acid methyl ester | 150456-85-2

• 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
• 英文名称: (3β,5β,7α,12α)-3-[(6-amino-1-oxohexyl)amino]-7,12-dihydroxycholan-24-oic acid methyl ester
• 英文别名: methyl (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(6-aminohexanoylamino)-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: 150456-85-2
• 化学式: C₃₁H₅₄N₂O₅
• 分子量: 534.78
• InChiKey: SVJAPNRKHXNTPB-LEYGBUAXSA-N

物化性质

• 沸点：
  682.9±55.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二亚乙基三胺五乙酸二酐 、 (3β,5β,7α,12α)-3-[(6-amino-1-oxohexyl)amino]-7,12-dihydroxycholan-24-oic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以69%的产率得到18-[[(3β,5β,7α,12α)-23-carboxy-7,12-dihydroxy-24-norcholan-3-yl]amino]-3,6,9-tris(carboxymethyl)-11,18-dioxo-3,6,9,12-tetraazaoctadecanoic acid
  参考文献：
  名称：

  Conjugates of Gadolinium Complexes to Bile Acids as Hepatocyte-Directed Contrast Agents for Magnetic Resonance Imaging

  摘要：

  A series of structurally different Gd(III) conjugates incorporating a bile acid moiety have been prepared. Polyaminopolycarboxylic ligands such as diethylenetriaminepentaacetic acid (DTPA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid (DOTA) have been selected as chelating subunit for the Gd(III) ion. Cholic acid, cholylglycine, and cholyltaurine have been incorporated as the bile acid moieties. In first generation conjugates the Gd(III) complex is linked to the carboxyl group of cholic acid. Second generation conjugates feature the attachment of the Gd(III) complex to the 3 position of the steroidic backbone of the bile acid. Finally, in third generation conjugates the Gd(III) complex is attached to the E nitrogen atom of cholyllysine. The conjugates are eliminated through the biliary route to a various extent (7.5 to 77% in rats) according to their structural features. Among the most promising terms, a second generation conjugate in which the Gd(III) complex is linked to cholic acid through the 3alpha hydroxy group seems to enter hepatocytes using the Na+/taurocholate transporter. Noticeably, some of the second generation conjugates are characterized by very high tolerabilities (LD50 up to 9.5 mmol/kg) after intravenous administration in mice.

  DOI：

  10.1021/jm0310683
• 作为产物：
  描述：

  (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid methyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.25h， 生成 (3β,5β,7α,12α)-3-[(6-amino-1-oxohexyl)amino]-7,12-dihydroxycholan-24-oic acid methyl ester
  参考文献：
  名称：

  Conjugates of Gadolinium Complexes to Bile Acids as Hepatocyte-Directed Contrast Agents for Magnetic Resonance Imaging

  摘要：

  A series of structurally different Gd(III) conjugates incorporating a bile acid moiety have been prepared. Polyaminopolycarboxylic ligands such as diethylenetriaminepentaacetic acid (DTPA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid (DOTA) have been selected as chelating subunit for the Gd(III) ion. Cholic acid, cholylglycine, and cholyltaurine have been incorporated as the bile acid moieties. In first generation conjugates the Gd(III) complex is linked to the carboxyl group of cholic acid. Second generation conjugates feature the attachment of the Gd(III) complex to the 3 position of the steroidic backbone of the bile acid. Finally, in third generation conjugates the Gd(III) complex is attached to the E nitrogen atom of cholyllysine. The conjugates are eliminated through the biliary route to a various extent (7.5 to 77% in rats) according to their structural features. Among the most promising terms, a second generation conjugate in which the Gd(III) complex is linked to cholic acid through the 3alpha hydroxy group seems to enter hepatocytes using the Na+/taurocholate transporter. Noticeably, some of the second generation conjugates are characterized by very high tolerabilities (LD50 up to 9.5 mmol/kg) after intravenous administration in mice.

  DOI：

  10.1021/jm0310683

文献信息

• BILE ACID CONJUGATES, DERIVATIVES THEREOF WITH METAL COMPLEXES AND RELATED USES
  申请人：BRACCO S.p.A.

  公开号：EP0760683B1

  公开（公告）日：2000-01-05
• US5649537A
  申请人：——

  公开号：US5649537A

  公开（公告）日：1997-07-22
• [EN] BILE ACID CONJUGATES, DERIVATIVES THEREOF WITH METAL COMPLEXES AND RELATED USES<br/>[FR] CONJUGUES D'ACIDE BILIAIRE, LEURS DERIVES FORMES AVEC DES COMPLEXES METALLIQUES ET UTILISATIONS ASSOCIEES
  申请人：BRACCO S.P.A.

  公开号：WO1995032741A1

  公开（公告）日：1995-12-07

  (EN) The invention relates to novel paramagnetic metal ion chelates and their use as contrast agents in the diagnostic technique known as 'magnetic resonance imaging' (M.R.I.).(FR) L'invention se rapporte à de nouveaux chélates d'ions métalliques paramagnétiques, ainsi qu'à leur utilisation comme agents de contraste dans le cadre de la technique diagnostique dite 'imagerie par résonance magnétique' (I.R.M.).