3α-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino-7α,12α-dihydroxy-5β-cholan-24-oic acid | 138582-77-1

• 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-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino-7α,12α-dihydroxy-5β-cholan-24-oic acid
• 英文别名: (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 138582-77-1
• 化学式: C₃₀H₄₂N₄O₇
• 分子量: 570.686
• InChiKey: CYVXKQVJEHKBNZ-FQDIFVGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  175
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3α-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino-7α,12α-dihydroxy-5β-cholan-24-oic acid 、 4-{3-[4-(3-amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-7,12-dihydroxy-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]-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p
• 作为产物：
  描述：

  胆酸甲酯 在 lithium hydroxide 、 sodium azide 、 偶氮二甲酸二异丙酯 、 水 、 碳酸氢钠 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 57.0h， 生成 3α-(7-nitro-2,1,3-benzoxadiazol-4-yl)amino-7α,12α-dihydroxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p

文献信息

• Stereodifferentiation in fluorescence quenching within cholic acid aggregates
  作者：M. Consuelo Cuquerella、Jana Rohacova、M. Luisa Marin、Miguel A. Miranda

  DOI：10.1039/c0cc00176g

  日期：——

  Two cholic acid (ChA) analogues, containing a 4-nitrobenzo-2-oxa-1,3-diazole (NBD) moiety at C-3, were incorporated into ChA aggregates and submitted to fluorescence quenching by the two enantiomers of several tryptophan derivatives. In all cases, a significant stereodifferentiation was observed; the most remarkable effect was found when comparing the 3α and the 3β diastereomers.

  两种胆酸（ChA）类似物的 C-3 位含有一个 4-硝基苯并-2-氧杂-1,3-二唑（NBD）分子，它们被加入到 ChA 聚集体中，并被几种色氨酸衍生物的两种对映体淬灭荧光。在所有情况下，都观察到了明显的立体差异；在比较 3α 和 3β 非对映异构体时，发现了最显著的效果。