(3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid phenyl methyl ester | 204063-16-1

• 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-amino-7,12-dihydroxycholan-24-oic acid phenyl methyl ester
• 英文别名: benzyl (4R)-4-[(3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-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]pentanoate
• CAS: 204063-16-1
• 化学式: C₃₁H₄₇NO₄
• 分子量: 497.718
• InChiKey: PYHYIXVYXBSMBK-JRFJFGBPSA-N

物化性质

• 沸点：
  611.5±55.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid phenyl methyl ester 在 palladium on activated charcoal 氰基磷酸二乙酯 、 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (3β(S),5β,7α,12α)-3-[[4-[bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]amino]-5-(1,1-dimethylethoxy)-1,5-dioxopentyl]amino]-7,12-dihydroxycholan-24-oic 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：

  benzyl cholate 在 叠氮磷酸二苯酯 、 水 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 生成 (3β,5β,7α,12α)-3-amino-7,12-dihydroxycholan-24-oic acid phenyl methyl ester
  参考文献：
  名称：

  从 3-Hydroxycholan-24-oic 酸酯制备 3-Aminocholan-24-oic 酸酯的一锅 Mitsunobu-Staudinger

  摘要：

  摘要 3-Hydroxycholan-24-oic酸酯通过与叠氮磷(DPPA)的Mitsunobu反应和中间体叠氮化合物在THF中的PPh3/H2O进行Staudinger还原反应，很容易转化为相应的3-氨基衍生物。

  DOI：

  10.1080/00397919808005079

文献信息

• Blood pool agents for nuclear magnetic resonance diagnostics
  申请人：Bracco Imaging S.p.A.

  公开号：EP1935435B1

  公开（公告）日：2017-09-06
• BLOOD POOL AGENTS FOR NUCLEAR MAGNETIC RESONANCE DIAGNOSTICS
  申请人：BRACCO IMAGING S.p.A.

  公开号：EP1140209B1

  公开（公告）日：2008-08-20