N⁶-[(phenylmethoxy)carbonyl]-N²-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-L-lysine methyl ester | 731009-53-3

• 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: N⁶-[(phenylmethoxy)carbonyl]-N²-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-L-lysine methyl ester
• 英文别名: methyl N6-((benzyloxy)carbonyl)-N2-((4R)-4-((3R,7R,10S,12S,13R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)-L-lysinate；N6-(phenylmethoxy)carbonyl-N2-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]-L-lysine methyl ester；methyl (2S)-6-(phenylmethoxycarbonylamino)-2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-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]hexanoate
• CAS: 731009-53-3
• 化学式: C₃₉H₆₀N₂O₈
• 分子量: 684.914
• InChiKey: IFILSBMPKLZWBD-OVJXNXTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁶-[(phenylmethoxy)carbonyl]-N²-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-L-lysine methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以99 %的产率得到methyl ((4R)-4-((3R,7R,10S,12S,13R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyl)-L-lysinate
  参考文献：
  名称：

  FLUORESCENT PROBES FOR IDENTIFICATION AND QUANTIFICATION OF HEPATIC TRANSPORTERS IN VITRO AND IN VIVO

  摘要：

  Fluorescent probe compounds comprising fluorescent cholic acid derivative are used for visualizing the influence of a candidate compound on biliary excretion in in vitro or in vivo biological models, including certain probes developed report on the activity of the bile salt export pump (BSEP). Visualization is done on hepatocyte cultures with formed bile canaliculi or on liver systems that are exposed to the fluorescent probes and the candidate compound. Visualization is done by fluorescence microscopy. The probes are particularly suitable for early screening of multiple candidate compounds.

  公开号：

  US20220308043A1
• 作为产物：
  描述：

  N6-Cbz-L-赖氨酸 在 对甲苯磺酸 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 26.25h， 生成 N⁶-[(phenylmethoxy)carbonyl]-N²-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-L-lysine 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

• Paramagnetic metal icon chelates and use thereof as contrast agents in
  申请人：Dibra S.p.A.

  公开号：US05649537A1

  公开（公告）日：1997-07-22

  Novel paramagnetic metal ion chelates and their use as contrast agents in the diagnostic technique known as "magnetic resonance imaging" (M.R.I.) of the gastrointestinal tract and particularly of the liver, are described. The novel compounds result from the conjugation of a bile acid with a chelating agent and are capable of chelating the ions of bivalent and trivalent metals. The compounds have formula A-L-B in which A is the residue of a bile acid and derivatives of a bile acid, B is the residue of a chelating agent of a bivalent or trivalent metal ion having an atomic number of 20 to 31, 39, 42, 43, 44, 49, 57 to 83, L is a ligand between A and B.

  本发明描述了新型顺磁性金属离子螯合物及其作为“磁共振成像”（M.R.I.）诊断技术中胃肠道和特别是肝脏的对比剂的使用。这些新型化合物是由胆酸与螯合剂结合而成，能够螯合二价和三价金属离子。该化合物的化学式为A-L-B，其中A是胆酸及其衍生物的残基，B是具有原子序数20到31、39、42、43、44、49、57到83的二价或三价金属离子的螯合剂残基，L是连接A和B之间的配体。
• 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