3β-azido-7β-hydroxy-5β-cholan-24-oic acid | 1232030-83-9

• 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
• 英文别名: 3β-azido-7β-hydroxy-5β-cholanic acid；(4R)-4-[(3S,5S,7S,8R,9S,10S,13R,14S,17R)-3-azido-7-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]pentanoic acid
• CAS: 1232030-83-9
• 化学式: C₂₄H₃₉N₃O₃
• 分子量: 417.592
• InChiKey: YKCJFMOBSSZJDJ-DNMBCGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-azido-7β-hydroxy-5β-cholan-24-oic acid 、 dihydroartesiminin 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 以45%的产率得到
  参考文献：
  名称：

  双氢青蒿素-胆汁酸杂交作为增强双氢青蒿素抗癌活性的有效方法。

  摘要：

  通过不同的合成方法制备了一系列基于天然产物胆汁酸和双氢青蒿素的杂化化合物，并研究了它们对 HL-60 白血病和 HepG2 肝细胞癌细胞系的体外生物活性。这些杂种中的大多数在双氢青蒿素和母体胆汁酸方面表现出显着改善的抗增殖活性。该系列的两个最有效的杂交体在 HL-60 和 HepG2 细胞中表现出相对于单独的双氢青蒿素的细胞毒活性分别增加了 10.5 倍和 15.4 倍。通过流式细胞术分析和蛋白质印迹分析获得了熊去氧胆酸杂合体诱导细胞凋亡的有力证据。

  DOI：

  10.1002/cmdc.201800756
• 作为产物：
  描述：

  3β-azido-7β-hydroxy-5β-cholan-24-oic acid methyl ester 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以99%的产率得到3β-azido-7β-hydroxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Cationic Heteroleptic Cyclometalated IridiumIII Complexes Containing Phenyl-Triazole and Triazole-Pyridine Clicked Ligands

  摘要：

  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。

  DOI：

  10.3390/molecules15032039

文献信息

• Bile acid toxicity structure–activity relationships: Correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A)
  作者：Ruchika Sharma、Ferenc Majer、Vijaya Kumar Peta、Jun Wang、Ray Keaveney、Dermot Kelleher、Aideen Long、John F. Gilmer

  DOI：10.1016/j.bmc.2010.07.030

  日期：2010.9

  The molecular mechanisms and interactions underlying bile acid cytotoxicity are important to understand for intestinal and hepatic disease treatment and prevention and the design of bile acid-based therapeutics.Bile acid lipophilicity is believed to be an important cytotoxicity determinant but the relationship is not well characterized. In this study we prepared new azido and other lipophilic BAs and altogether assembled a panel of 37 BAs with good dispersion in lipophilicity as reflected in RPTLC R-Mw. The MTT cell viability assay was used to assess cytotoxicity over 24 h in the HET-1A cell line (oesophageal). RMw values inversely correlated with cell viability for the whole set (r(2) = 0.6) but this became more significant when non-acid compounds were excluded (r(2) = 0.82, n = 29). The association in more homologous subgroups was stronger still (r(2) > 0.96). None of the polar compounds were cytotoxic at 500 mu M, however, not all lipophilic BAs were cytotoxic. Notably, apart from the UDCA primary amide, lipophilic neutral derivatives of UDCA were not cytotoxic. Finally, CDCA, DCA and LagoDCA were prominent outliers being more toxic than predicted by R-Mw. In a hepatic carcinoma line, lipophilicity did not correlate with toxicity except for the common naturally occurring bile acids and their conjugates. There were other significant differences in toxicity between the two cell lines that suggest a possible basis for selective cytotoxicity. The study shows: (i) azido substitution in BAs imparts lipophilicity and toxicity depending on orientation and ionizability; (ii) there is an inverse correlation between R-Mw and toxicity that has good predictive value in homologous sets; (iii) lipophilicity is a necessary but apparently not sufficient characteristic for BA cytocidal activity to which it appears to be indirectly related. (C) 2010 Elsevier Ltd. All rights reserved.
• 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。
• Dihydroartemisinin–Bile Acid Hybridization as an Effective Approach to Enhance Dihydroartemisinin Anticancer Activity
  作者：Elena Marchesi、Nicola Chinaglia、Massimo L. Capobianco、Paolo Marchetti、Tzu‐En Huang、Hao‐Cheng Weng、Jih‐Hwa Guh、Lih‐Ching Hsu、Daniela Perrone、Maria Luisa Navacchia

  DOI：10.1002/cmdc.201800756

  日期：2019.4.3

  on natural products-bile acids and dihydroartemisinin-were prepared by different synthetic methodologies and investigated for their in vitro biological activity against HL-60 leukemia and HepG2 hepatocellular carcinoma cell lines. Most of these hybrids presented significantly improved antiproliferative activities with respect to dihydroartemisinin and the parent bile acid. The two most potent hybrids

  通过不同的合成方法制备了一系列基于天然产物胆汁酸和双氢青蒿素的杂化化合物，并研究了它们对 HL-60 白血病和 HepG2 肝细胞癌细胞系的体外生物活性。这些杂种中的大多数在双氢青蒿素和母体胆汁酸方面表现出显着改善的抗增殖活性。该系列的两个最有效的杂交体在 HL-60 和 HepG2 细胞中表现出相对于单独的双氢青蒿素的细胞毒活性分别增加了 10.5 倍和 15.4 倍。通过流式细胞术分析和蛋白质印迹分析获得了熊去氧胆酸杂合体诱导细胞凋亡的有力证据。