3α,3'α-Dihydroxy-5β-cholan-24-oic acid piperazine diamine | 308321-38-2

• 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: 3α,3'α-Dihydroxy-5β-cholan-24-oic acid piperazine diamine
• 英文别名: 3α,3'α-dihydroxy-5β-cholan-24-oic acid piperazine diamide；N,N'-bis(3α-hydroxy-5β-cholan-24-oyl)-piperazine；(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-[4-[(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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]piperazin-1-yl]pentan-1-one
• CAS: 308321-38-2
• 化学式: C₅₂H₈₆N₂O₄
• 分子量: 803.266
• InChiKey: KNSRHJSIWNUVEI-CHYUCTTLSA-N

物化性质

• 熔点：
  120-123 °C(Solvent: Ethyl acetate)
• 密度：
  1.084±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对苯二甲酸 、 3α,3'α-Dihydroxy-5β-cholan-24-oic acid piperazine diamine 在 4-二甲氨基吡啶 、 2,6-二氯苯甲酰氯 作用下， 以 甲苯 为溶剂， 反应 44.0h， 以9%的产率得到3α,3'α-Dihydroxy-5β-cholan-24-oic acid piperazine diamine terephthalic acid diester
  参考文献：
  名称：

  Bile Acid-Piperazine Diamides: Novel Steroidal Templates in Syntheses of Supramolecular Hosts: Isomeric Pyridine-n-carboxy Containing Dimers and a Cholaphane

  摘要：

  新型甾体二聚体：3α,3′α-二羟基-5β-cholan-24-oic 酸哌嗪二酰胺 3、其 3α,3′α-双(三氟乙酰氧基) 保护的衍生物 2 和 3α,3′α ±-双(吡啶-n-羧基, n = 2-4)衍生物4-6及其Ag+-配合物已被制备。还通过山口法与对苯二甲酸环化3，合成了一种新型的cholaphane 7。通过 13C 和 15N NMR 化学位移和 MALDI-TOF MS 对产物进行表征。此外，还进行了 3 和 7 的 MO 计算 (PM3)。

  DOI：

  10.1055/s-2000-7113
• 作为产物：
  描述：

  以 1,4-二氧六环 、 水 为溶剂， 反应 2.5h， 生成 3α,3'α-Dihydroxy-5β-cholan-24-oic acid piperazine diamine
  参考文献：
  名称：

  1H-, 13C-, and 15N-NMR and ESI-TOF+ MS studies of a supramolecular complex of silver(I) and a cholaphane

  摘要：

  A novel application of the mixed anhydride procedure for synthesising lithocholic acid piperazine diamide, an important intermediate in designing bile acid-based supramolecular host molecules, is reported. The synthesis of a thiophene-contaming cholaphane with transition metal complexation ability and H-1-, C-13-, and N-15-NMR as well as ESI-TOF+ MS spectral characterisation of the ligand and its Ag(I) complex are included. The coordination of the Ag(I) ion as well as an ability of the cholaphane to recognise Ag(I) ion over alkali metal ions, especially potassium ion, is discussed. The possible medical applications are also presented. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)02096-x

文献信息

• Multinuclear magnetic resonance, electrospray ionization time-of-flight mass spectral and molecular modelling characterization of lithocholic acid amide esters with various nitrogen heterocycles
  作者：Elina Virtanen、Jari Tamminen、Mervi Haapala、Pia Mänttäri、Reijo Kauppinen、Erkki Kolehmainen

  DOI：10.1002/mrc.1218

  日期：2003.8

  1H, 13C and 15N NMR and electrospray ionization time-of-flight mass spectrometric characterizations of five lithocholate esters of piperazine diamides are described. Two of them are cholaphane-type cyclic structures esterified with 2,2′-bipyridine-4,4 ′ - and pyridine-2,6-dicarboxylic acid and the other three esters are open structures comprising two or four lithocholyl residues. The conformational preferences of the dimeric congeners were examined by using molecular modelling and variable-temperature 1H NMR techniques. Copyright © 2003 John Wiley & Sons, Ltd.

  本文描述了五种石胆酸酯哌嗪双酰胺的1H、13C和15N核磁共振以及电喷雾电离飞行时间质谱特性。其中两种为胆甾烷型环状结构，通过2,2′-联吡啶-4,4′-和吡啶-2,6-二羧酸酯化，另外三种酯为开链结构，包含两个或四个石胆酰基残基。通过分子建模和变温1H核磁共振技术考察了其二聚体的构象偏好。版权所有 © 2003 John Wiley & Sons, Ltd.
• Synthesis of Novel Amide-Linked Dimers of Lithocholic Acid
  作者：Roman Joachimiak、Monika Piasecka、Zdzisław Paryzek

  DOI：10.3184/030823408x318325

  日期：2008.5

  An efficient synthesis of lithocholic amides and amide-linked dimers under mild conditions is described. New o-, m- and p-phenylenediamine-derived dimers of lithocholic acid were synthesised by the activation of the carboxyl group of the bile acid as a mixed anhydride resulting from the reaction of the acid with ethyl chloroformate. The reduction of lithocholic amides afforded the corresponding 24-amino-5β-cholane

  描述了在温和条件下有效合成石胆酸酰胺和酰胺连接的二聚体。新的邻、间和对苯二胺衍生的石胆酸二聚体是通过活化胆汁酸的羧基作为酸与氯甲酸乙酯反应产生的混合酸酐来合成的。石胆酸酰胺的还原得到相应的 24-氨基-5β-胆烷衍生物。所有化合物均通过 IR、1H 和 13C NMR 和质谱进行表征。