3β-azido-7β-hydroxy-5β-cholan-24-oic acid methyl ester | 142974-48-9

• 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-azido-7β-hydroxy-5β-cholan-24-oic acid methyl ester
• 英文别名: 24-methyl 3β-azido-7β-hydroxy-5β-cholanoate
• CAS: 142974-48-9
• 化学式: C₂₅H₄₁N₃O₃
• 分子量: 431.619
• InChiKey: OCPWSSCYDOGFCX-LWNNJCQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  95.29
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3β-azido-7β-hydroxy-5β-cholan-24-oic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 123.0h， 生成 3β-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino-7β-hydroxy-5β-cholanoic acid
  参考文献：
  名称：

  New fluorescent bile acids: Synthesis, chemical characterization, and disastereoselective uptake by Caco-2 cells of 3-deoxy 3-NBD-amino deoxycholic and ursodeoxycholic acid

  摘要：

  Deoxycholic acid (DCA), a secondary bile acid (BA), and ursodeoxycholic acid (UDCA), a tertiary BA, cause opposing effects in vivo and in cell suspensions. Fluorescent analogues of DCA and UDCA could help investigate important questions about their cellular interactions and distribution.We have prepared a set of isomeric 3 alpha- and 3 beta-amino analogues of UDCA and DCA and derivatised these with the discrete fluorophore, 4-nitrobenzo-2-oxa-1,3-diazol (NBD), forming the corresponding four fluorescent adducts. These absorb in the range 465-470 nm and fluoresce at approx. 535 nm.In order to determine the ability of the new fluorescent bile acids to mimic the parents, their uptake was studied using monolayers of Caco-2 cells, which are known to express multiple proteins of the organic anion-transporting peptide (OATP) subfamily of transporters. Cellular uptake was monitored over time at 4 and 37 degrees C to distinguish between passive and active transport.All four BA analogues were taken up but in a strikingly stereo-and structure-specific manner, suggesting highly discriminatory interactions with transporter protein(s). The alpha-analogues of DCA and to a lesser extent UDCA were actively transported, whereas the beta-analogues were not. The active transport process was saturable, with Michaelis-Menten constants for 3 alpha-NBD DCA (5) being K-m = 42.27 +/- 12.98 mu M and V-max = 2.8 +/- 0.4 nmol/(mg protein*min) and for 3 alpha-NBD UDCA (3) K-m = 28.20 +/- 7.45 mu M and V-max = 1.8 +/- 0.2 nmol/(mg protein(*)min). These fluorescent bile acids are promising agents for investigating questions of bile acid biology and for detection of bile acids and related organic anion transport processes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.002
• 作为产物：
  描述：

  24-methyl 3β-azido-7β-formyloxy-5β-cholanoate 在 甲醇 、 乙酰氯 作用下， 以97%的产率得到3β-azido-7β-hydroxy-5β-cholan-24-oic acid methyl ester
  参考文献：
  名称：

  New fluorescent bile acids: Synthesis, chemical characterization, and disastereoselective uptake by Caco-2 cells of 3-deoxy 3-NBD-amino deoxycholic and ursodeoxycholic acid

  摘要：

  Deoxycholic acid (DCA), a secondary bile acid (BA), and ursodeoxycholic acid (UDCA), a tertiary BA, cause opposing effects in vivo and in cell suspensions. Fluorescent analogues of DCA and UDCA could help investigate important questions about their cellular interactions and distribution.We have prepared a set of isomeric 3 alpha- and 3 beta-amino analogues of UDCA and DCA and derivatised these with the discrete fluorophore, 4-nitrobenzo-2-oxa-1,3-diazol (NBD), forming the corresponding four fluorescent adducts. These absorb in the range 465-470 nm and fluoresce at approx. 535 nm.In order to determine the ability of the new fluorescent bile acids to mimic the parents, their uptake was studied using monolayers of Caco-2 cells, which are known to express multiple proteins of the organic anion-transporting peptide (OATP) subfamily of transporters. Cellular uptake was monitored over time at 4 and 37 degrees C to distinguish between passive and active transport.All four BA analogues were taken up but in a strikingly stereo-and structure-specific manner, suggesting highly discriminatory interactions with transporter protein(s). The alpha-analogues of DCA and to a lesser extent UDCA were actively transported, whereas the beta-analogues were not. The active transport process was saturable, with Michaelis-Menten constants for 3 alpha-NBD DCA (5) being K-m = 42.27 +/- 12.98 mu M and V-max = 2.8 +/- 0.4 nmol/(mg protein*min) and for 3 alpha-NBD UDCA (3) K-m = 28.20 +/- 7.45 mu M and V-max = 1.8 +/- 0.2 nmol/(mg protein(*)min). These fluorescent bile acids are promising agents for investigating questions of bile acid biology and for detection of bile acids and related organic anion transport processes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.002

文献信息

• Cationic Heteroleptic Cyclometalated IridiumIII Complexes Containing Phenyl-Triazole and Triazole-Pyridine Clicked Ligands
  作者：Marco Felici、Pablo Contreras-Carballada、Jan M. M. Smits、Roeland J. M. Nolte、René M. Williams、Luisa De Cola、Martin C. Feiters

  DOI：10.3390/molecules15032039

  日期：——

  Novel heteroleptic iridium complexes containing the 1-substituted-4-phenyl-1H-1,2,3-triazole (phtl) cyclometalating ligand have been synthesized. The 3+2 Huisgen dipolar cycloaddition method (‘click’ chemistry) was utilized to prepare a class of bidentate ligands (phtl) bearing different substituents on the triazole moiety. By using various ligands (phtl-R1 and pytl-R2) (R1=adamantane, methyl and R2=adamantane, methyl, β-cyclodextrin, ursodeoxycholic acid), we prepared a small library of new luminescent ionic iridium complexes [Ir(phtr-R1)2(pytl-R2)]Cl and report on their photophysical properties. The flexibility of the clicking approach allows a straightforward control on the chemical-physical properties of the complexes by varying the nature of the substituent on the ligand.

  合成了含有1-取代-4-苯基-1H-1,2,3-三唑（phtl）环金属配体的新型异配位铱络合物。利用3+2 Huisgen偶极环加成方法（“点击”化学）制备了一类在三唑部分具有不同取代基的双齿配体（phtl）。通过使用不同的配体（phtl-R1和pytl-R2）（R1=适度烷烃、甲基，R2=适度烷烃、甲基、β-环糊精、熊去氧胆酸），我们制备了一小类新的发光离子铱络合物[Ir(phtr-R1)2(pytl-R2)]Cl，并报告了它们的光物理性质。“点击”方法的灵活性使得通过改变配体上取代基的性质，可以简单地控制络合物的化学-物理性质。