(3β,5β,12α)-3-[[(4S)-4-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-4-carboxy-1-oxobutyl]amino]-12-hydroxycholan-24-oic acid | 280765-83-5

• 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,12α)-3-[[(4S)-4-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-4-carboxy-1-oxobutyl]amino]-12-hydroxycholan-24-oic acid
• 英文别名: [3β(S),5β,12α]-3-[[4-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-4-carboxy-1-oxobutyl]amino]-12-hydroxycholan-24-oic acid；(2S)-2-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-5-[[(3S,5R,8R,9S,10S,12S,13R,14S,17R)-17-[(2R)-4-carboxybutan-2-yl]-12-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-5-oxopentanoic acid
• CAS: 280765-83-5
• 化学式: C₄₁H₆₆N₄O₁₄
• 分子量: 838.993
• InChiKey: NCPSJGFHSXJCCR-DOXATILGSA-N

物化性质

• 熔点：
  185-190 °C (decomp)
• 沸点：
  1050.2±65.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  59
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  283
• 氢给体数：
  8
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (3β,5β,12α)-3-[[(4S)-4-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-4-carboxy-1-oxobutyl]amino]-12-hydroxycholan-24-oic acid 以88的产率得到trisodium;2-[2-[2-[bis(carboxylatomethyl)amino]ethyl-[(1S)-1-carboxy-4-[[(3R,5R,8R,9R,10R,12R,13S,14S,17R)-17-[(2R)-4-carboxybutan-2-yl]-12-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-4-oxobutyl]amino]ethyl-(carboxymethyl)amino]acetate;gadolinium
  参考文献：
  名称：

  Blood pool agents for nuclear magnetic resonance diagnostics

  摘要：

  本发明涉及与钆或锰离子结合的胆酸共轭物及其盐，以及与生理兼容的有机或无机碱的复合物，其制备过程和含有它们的对比剂诊断药物组成物。

  公开号：

  EP1935435A2
• 作为产物：
  描述：

  1-benzyl 2-methyl (S)-5-oxopyrrolidine-1,2-dicarboxylate 在 5%-palladium/activated carbon lithium hydroxide 、 水 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 182.66h， 生成 (3β,5β,12α)-3-[[(4S)-4-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]-4-carboxy-1-oxobutyl]amino]-12-hydroxycholan-24-oic acid
  参考文献：
  名称：

  Blood pool agents for nuclear magnetic resonance diagnostics

  摘要：

  公开号：

  EP1935435B1

文献信息

• Scale-Up of Trisodium [(3β,5β,12α)-3-[[4(<i>S</i>)-4-[Bis[2-[bis[(carboxy-<i>kO</i>)methyl]amino-<i>kN</i>]ethyl]amino-<i>kN</i>]-4-(carboxy-<i>kO</i>)-1-oxobutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography
  作者：Pier Lucio Anelli、Marino Brocchetta、Luciano Lattuada、Giuseppe Manfredi、Pierfrancesco Morosini、Marcella Murru、Daniela Palano、Marco Sipioni、Massimo Visigalli

  DOI：10.1021/op900008a

  日期：2009.7.17

  Process chemistry involved in the discovery and development routes to trisodium [(3 beta,5 beta,12(alpha)-3-[[4(S)-4-[bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]4-(carboxy-kO)-1-oxobutyl]- amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)] (B22956/1) starting from L-glutamic acid and (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid is described. The best process is based on seven chemical steps and overcomes difficult purification protocols. Such process has been successfully implemented to prepare multikilogram batches of the target compound in 20% overall yield from (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid.