N-(3β-hydroxy-Δ⁵-cholen-24-oyl)glycine | 69776-17-6

• 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: N-(3β-hydroxy-Δ⁵-cholen-24-oyl)glycine
• 英文别名: glyco-3β-hydroxy-5-cholen-24-oic acid；3β-hydroxy-5-cholen-24-oyl-glycin；3β-hydroxy-5-cholenoyl glycine；3-Hydroxy-5-cholenoylglycine；2-[[(4R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
• CAS: 69776-17-6
• 化学式: C₂₆H₄₁NO₄
• 分子量: 431.616
• InChiKey: YVPDWGJLXBNGPX-ZHRHZKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3β-hydroxy-Δ⁵-cholen-24-oyl)glycine 在 ClSO₃ 作用下， 以 吡啶 为溶剂， 反应 1.0h， 以116 mg的产率得到glyco-3β-hydroxy-5-cholen-24-oic acid 3-sulfate
  参考文献：
  名称：

  Determination of 3β-hydroxy-5-cholen-24-OIC acid and its sulfate in human serum by gas chromatography-mass spectrometry

  摘要：

  The glycine conjugate of 3 beta-hydroxy-5-cholen-24-oic acid and its sulfate labeled with deuterium at the C-2, -4, and -23 positions were synthesized. A highly sensitive and specific quantitative assay of the bile acid has been developed by selected ion monitoring in gas chromatography-mass spectrometry of the methyl ester trimethylsilyl ether derivatives using the deuterium labeled conjugates as internal standards. Calibration curves for the bile acid and its sulfate exhibited a linear relationship over the range of 0.01-100 micrograms/ml in human serum.

  DOI：

  10.1016/s0039-128x(84)80015-x
• 作为产物：
  描述：

  methyl 3β-hydroxy-5-cholen-24-oyl-glycinate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以0.8 g的产率得到N-(3β-hydroxy-Δ⁵-cholen-24-oyl)glycine
  参考文献：
  名称：

  Preparation and antigenic properties of methyl 3.BETA.-hydroxy-19-oxo-5-cholen-24-oyl-glycinate 19-(O-carboxymethyl)oxime-bovine serum albumin conjugate.

  摘要：

  3β-羟基-5-胆-24-酰基-甘氨酸-牛血清白蛋白（BSA）缀合物的制备和抗原特性，其中半抗原通过C-上的（O-羧甲基）肟桥与载体蛋白连接对类固醇部分的19个位置进行了描述。兔体内针对该抗原产生的抗体对3β-羟基-5-胆-24-酰基-甘氨酸具有高滴度和特异性，与各种胆汁酸无明显交叉反应。

  DOI：

  10.1248/cpb.32.3088

文献信息

• Δ5-Cholenoyl-amino acids as selective and orally available antagonists of the Eph–ephrin system
  作者：Riccardo Castelli、Massimiliano Tognolini、Federica Vacondio、Matteo Incerti、Daniele Pala、Donatella Callegari、Simona Bertoni、Carmine Giorgio、Iftiin Hassan-Mohamed、Ilaria Zanotti、Antonella Bugatti、Marco Rusnati、Claudio Festuccia、Silvia Rivara、Elisabetta Barocelli、Marco Mor、Alessio Lodola

  DOI：10.1016/j.ejmech.2015.08.048

  日期：2015.10

  developing small-molecule antagonists of the Eph receptors are still in their initial stage as available compounds suffer from pharmacological drawbacks, limiting their application in vitro and in vivo. In the present work, we report the design, synthesis and evaluation of structure-activity relationships of a class of Δ(5)-cholenoyl-amino acid conjugates as Eph-ephrin antagonists. As a major achievement

  Eph受体-ephrin系统是新型抗血管生成疗法发展的新兴目标。旨在开发Eph受体小分子拮抗剂的研究计划仍处于起步阶段，因为可用的化合物存在药理学缺陷，限制了它们在体内和体外的应用。在目前的工作中，我们报告设计，合成和评估一类Δ（5）-胆酰基-氨基酸缀合物作为Eph-ephrin拮抗剂的结构-活性关系。作为我们探索的一项重大成就，我们确定了N-（3β-羟基-Δ（5）-cholen-24-oyl）-L-色氨酸（UniPR1331）是有效的Eph-ephrin系统小分子拮抗剂。内皮细胞中的抗血管生成剂
• Preparation and antigenic properties of methyl 3.BETA.-hydroxy-19-oxo-5-cholen-24-oyl-glycinate 19-(O-carboxymethyl)oxime-bovine serum albumin conjugate.
  作者：SHOICHIRO YAMAUCHI、MASAHARU KOJIMA、FUMIO NAKAYAMA

  DOI：10.1248/cpb.32.3088

  日期：——

  The preparation and antigenic properties of 3β-hydroxy-5-cholen-24-oyl-glycine-bovine serum albumin (BSA) conjugate in which the hapten is linked to the carrier protein through an (O-carboxymethyl) oxime bridge at the C-19 position on the steroid portion are described. Antibody raised against the antigen in rabbits possessed high titer and specificity to 3β-hydroxy-5-cholen-24-oyl-glycine, exhibiting no significant cross-reactions with various bile acids.

  3β-羟基-5-胆-24-酰基-甘氨酸-牛血清白蛋白（BSA）缀合物的制备和抗原特性，其中半抗原通过C-上的（O-羧甲基）肟桥与载体蛋白连接对类固醇部分的19个位置进行了描述。兔体内针对该抗原产生的抗体对3β-羟基-5-胆-24-酰基-甘氨酸具有高滴度和特异性，与各种胆汁酸无明显交叉反应。
• Determination of 3β-hydroxy-5-cholen-24-OIC acid and its sulfate in human serum by gas chromatography-mass spectrometry
  作者：M TOHMA、H WAJIMA、R MAHARA、T KUROSAWA、I MAKINO

  DOI：10.1016/s0039-128x(84)80015-x

  日期：1984.7

  The glycine conjugate of 3 beta-hydroxy-5-cholen-24-oic acid and its sulfate labeled with deuterium at the C-2, -4, and -23 positions were synthesized. A highly sensitive and specific quantitative assay of the bile acid has been developed by selected ion monitoring in gas chromatography-mass spectrometry of the methyl ester trimethylsilyl ether derivatives using the deuterium labeled conjugates as internal standards. Calibration curves for the bile acid and its sulfate exhibited a linear relationship over the range of 0.01-100 micrograms/ml in human serum.