3α-azido-7β-hydroxy-5β-cholan-24-oic acid | 1253736-45-6

• 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: 3α-azido-7β-hydroxy-5β-cholan-24-oic acid
• 英文别名: 3α-azido-7β-hydroxy-5β-cholanic acid；3α-zido-7β-hydroxy-5β-cholanoate；(4R)-4-[(3R,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: 1253736-45-6
• 化学式: C₂₄H₃₉N₃O₃
• 分子量: 417.592
• InChiKey: YKCJFMOBSSZJDJ-UZVSRGJWSA-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：

  3α-azido-7β-hydroxy-5β-cholan-24-oic acid 在 copper(ll) sulfate pentahydrate 、 氯甲酸乙酯 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  结合三唑部分的核苷-胆汁酸的合理设计用于抗癌评估和SAR探索。

  摘要：

  本文中，我们报告了通过将2'-脱氧腺苷，2'-脱氧鸟苷，2'-脱氧尿苷以及腺苷和鸟苷衍生物与化学-，尿嘧啶-氨基磺酸酯结合而制备的核苷-胆汁酸缀合物文库的合成和生物学评估。 ，通过点击反应，去甲壳基，去甲壳基，去甲磺基和牛磺去氧胆酸衍生物。在体外针对白血病K562和HCT116结肠癌以及在正常成纤维细胞上测试了结合有三唑部分的新的核苷-胆汁酸缀合物。六种化合物对所选的癌症细胞系表现出令人感兴趣的抗增殖活性，对正常的成纤维细胞没有细胞毒性作用。还研究了可能的结构活性关系。

  DOI：

  10.3390/molecules22101710
• 作为产物：
  描述：

  熊去氧胆酸 在 咪唑 、 sodium azide 、 硫酸 、 三苯基膦 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.58h， 生成 3α-azido-7β-hydroxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  通过正交点击反应的荧光标记辅助合成胆汁酸-双膦酸酯共轭物：获得潜在的抗吸收性骨药物的途径

  摘要：

  据报道，合成了少量新的胆汁酸-双膦酸盐（BA-BP）偶联物作为潜在的候选药物。所披露的方法分别依赖于BA支架的头尾位置上的叠氮化物和硫醇官能团的安装以及随后通过正交点击反应（铜催化的叠氮化物-炔环加成，硫醇-烯或硫醇-炔偶联）的修饰）引入BP单元和荧光团。由于通过标准程序难以分离靶标结合物，因此该方法最终以具有轻质荧光标签的BA支架功能化，从而通过荧光固相萃取快速有效地纯化中间体和最终产物。

  DOI：

  10.1039/c7ob00774d

文献信息

• NO Photoreleaser-Deoxyadenosine and -Bile Acid Derivative Bioconjugates as Novel Potential Photochemotherapeutics
  作者：Maria Luisa Navacchia、Aurore Fraix、Nicola Chinaglia、Eleonora Gallerani、Daniela Perrone、Venera Cardile、Adriana C. E. Graziano、Massimo L. Capobianco、Salvatore Sortino

  DOI：10.1021/acsmedchemlett.6b00257

  日期：2016.10.13

  This contribution reports the synthesis of some novel bioconjugates with anticancer activity and able to release nitric oxide (NO) under visible light excitation. The 4-nitro-2-(trifluoromethyl)aniline derivative, a suitable NO photodonor, was conjugated with 2′-deoxyadenosine and urso- and cheno-deoxycholic acid derivatives, through a thioalkylic chain or the 4-alkyl-1,2,3-triazole moiety. Photochemical

  该贡献报告了一些具有抗癌活性并能够在可见光激发下释放一氧化氮（NO）的新型生物共轭物的合成。通过硫代烷基链或4-烷基-1,2,3，将合适的NO光供体4-硝基-2-（三氟甲基）苯胺衍生物与2'-脱氧腺苷以及熊-和奇脱氧胆酸衍生物偶联。 -三唑部分。光化学实验表明，在可见光输入的唯一控制下，NO从2'-脱氧腺苷和熊去氧胆酸共轭物中有效释放。为研究在体外是针对白血病K562和结肠癌HCT116细胞系的抗增殖活性报告为所有化合物以及photocytotoxicity针对HCT116为例。
• 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.
• Fluorous-tag assisted synthesis of bile acid–bisphosphonate conjugates via orthogonal click reactions: an access to potential anti-resorption bone drugs
  作者：Chiara Massarenti、Olga Bortolini、Giancarlo Fantin、Dario Cristofaro、Daniele Ragno、Daniela Perrone、Elena Marchesi、Gianluca Toniolo、Alessandro Massi

  DOI：10.1039/c7ob00774d

  日期：——

  candidates is reported. The disclosed methodology relied on the installation of azide and thiol functionalities at the head and tail positions, respectively, of the BA scaffold and its subsequent decoration by orthogonal click reactions (copper-catalyzed azide–alkyne cycloaddition, thiol–ene or thiol–yne coupling) to introduce BP units and a fluorophore. Because of the troublesome isolation of the target

  据报道，合成了少量新的胆汁酸-双膦酸盐（BA-BP）偶联物作为潜在的候选药物。所披露的方法分别依赖于BA支架的头尾位置上的叠氮化物和硫醇官能团的安装以及随后通过正交点击反应（铜催化的叠氮化物-炔环加成，硫醇-烯或硫醇-炔偶联）的修饰）引入BP单元和荧光团。由于通过标准程序难以分离靶标结合物，因此该方法最终以具有轻质荧光标签的BA支架功能化，从而通过荧光固相萃取快速有效地纯化中间体和最终产物。
• Rational Design of Nucleoside–Bile Acid Conjugates Incorporating a Triazole Moiety for Anticancer Evaluation and SAR Exploration
  作者：Maria Navacchia、Elena Marchesi、Lara Mari、Nicola Chinaglia、Eleonora Gallerani、Riccardo Gavioli、Massimo Capobianco、Daniela Perrone

  DOI：10.3390/molecules22101710

  日期：——

  Herein we report a study on the synthesis and biological evaluation of a library of nucleoside-bile acid conjugates prepared by combining 2'-deoxyadenosine, 2'-deoxyguanosine, 2'-deoxyuridine as well as adenosine and guanosine derivatives with cheno-, urso-, nor-cheno-, nor-urso- and taurourso-desoxycholic acid derivatives by means of the click reaction. The new nucleoside-bile acid conjugates incorporating

  本文中，我们报告了通过将2'-脱氧腺苷，2'-脱氧鸟苷，2'-脱氧尿苷以及腺苷和鸟苷衍生物与化学-，尿嘧啶-氨基磺酸酯结合而制备的核苷-胆汁酸缀合物文库的合成和生物学评估。 ，通过点击反应，去甲壳基，去甲壳基，去甲磺基和牛磺去氧胆酸衍生物。在体外针对白血病K562和HCT116结肠癌以及在正常成纤维细胞上测试了结合有三唑部分的新的核苷-胆汁酸缀合物。六种化合物对所选的癌症细胞系表现出令人感兴趣的抗增殖活性，对正常的成纤维细胞没有细胞毒性作用。还研究了可能的结构活性关系。