2-[[(3β,5β,7α,12α)-3-[(aminoacetyl)amino]-7,12-dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic acid | 737736-89-9

• 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: 2-[[(3β,5β,7α,12α)-3-[(aminoacetyl)amino]-7,12-dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic acid
• 英文别名: 2-[[(4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[(2-aminoacetyl)amino]-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]pentanoyl]amino]ethanesulfonic acid
• CAS: 737736-89-9
• 化学式: C₂₈H₄₉N₃O₇S
• 分子量: 571.779
• InChiKey: LQQCKXKGSSLAJY-XZGGLZACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  187
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  二亚乙基三胺五乙酸二酐 、 2-[[(3β,5β,7α,12α)-3-[(aminoacetyl)amino]-7,12-dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic acid 在 水 、 sodium hydroxide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以57%的产率得到(3β,5β,7α,12α)-3-[[N-[N-[N-[2-[2-[bis(carboxymethyl)amino]ethyl] (carboxymethyl)amino]ethyl]-N-(carboxymethyl)glycyl]glycyl]amino]-7,12-dihydroxy-N-(2-sulfoethyl)cholan-24-amide
  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 盐酸 、 sodium hydroxide 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.42h， 生成 2-[[(3β,5β,7α,12α)-3-[(aminoacetyl)amino]-7,12-dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic 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