3-azidolithocholic acid methyl ester | 799271-33-3

• 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: 3-azidolithocholic acid methyl ester
• 英文别名: methyl 3-azidolithocholate；methyl 3β-azido-5β-cholan-24-oate；methyl 3β-azido-5β-cholanate；Methyl 3beta-azido-5beta-cholan-24-oate；methyl (4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-azido-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
• CAS: 799271-33-3
• 化学式: C₂₅H₄₁N₃O₂
• 分子量: 415.619
• InChiKey: NYSMBZFKIVPNHO-ARCWCCGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-azidolithocholic acid methyl ester 在 1,3-丙二硫醇 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以72%的产率得到3β-aminolithocholic acid methyl ester
  参考文献：
  名称：

  Design and Synthesis of Novel N-Acetylgalactosamine-Terminated Glycolipids for Targeting of Lipoproteins to the Hepatic Asialoglycoprotein Receptor

  摘要：

  A novel glycolipid has been prepared that contains a cluster glycoside with an unusually high affinity for the asialoglycoprotein receptor (ASGPr) and a bile acid moiety that mediates stable incorporation into lipidic particles. The glycolipid spontaneously associated with low-density lipoproteins (LDL) and high-density lipoproteins (HDL) within human and murine plasma, and loading of lipoproteins with this glycolipid resulted in an efficient dose-dependent recognition and uptake of LDL and HDL by the liver (and not by spleen) upon intravenous injection into wild-type mice. Preinjection with asialoorosomucoid largely inhibited the uptake, establishing that both HDL and LDL were selectively recognized and processed by the ASGPr on liver parenchymal cells. Finally, repeated intravenous administration of the glycolipid to hyperlipidemic LDL receptor-deficient mice evoked an efficient and persistent cholesterol-lowering effect. These results indicate that the glycolipid may be a promising alternative for the treatment of hyperlipidemic patients who do not respond sufficiently to current cholesterol-lowering therapies.

  DOI：

  10.1021/jm049481d
• 作为产物：
  描述：

  石胆酸 在 吡啶 、 盐酸 、 sodium azide 作用下， 以 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 3-azidolithocholic acid methyl ester
  参考文献：
  名称：

  单击化学：取代类固醇，皂角苷和洋地黄类似物的杂环的有效合成。

  摘要：

  铜催化的叠氮化物-炔烃环加成反应（CuAAC）已用于高产，高产的含1,2,3-三唑类固醇的构建。炔丙基糖苷和甾类叠氮化物作为反应伴侣的组合允许合成一类特权的天然产物类似物。该方案的多功能性使该化学成为合成目标分子的有用的有吸引力的方法。 点击化学-1,2,3-三唑-糖-类固醇-皂苷-洋地黄

  DOI：

  10.1055/s-0031-1289606

文献信息

• CuAAC Synthesis and Anion Binding Properties of Bile Acid Derived Tripodal Ligands
  作者：Dmitry A. Erzunov、Gennadij V. Latyshev、Alexey D. Averin、Irina P. Beletskaya、Nikolay V. Lukashev

  DOI：10.1002/ejoc.201500835

  日期：2015.10

  24-5β-cholanetriazolyl derivatives of phosphorus acids, which contained anion-binding triazolium sites and hydrophobic cholane residues. The influence of the location of the triazolium moiety (in 3α-, 3β-position) on fluoride-ion complexation was investigated. The anion-binding properties of tris(triazolium) ligands were studied for a series of inorganic and organic anions and high complexation constants were

  铜催化的叠氮化物-炔环加成反应用于制备一系列磷酸的双和三-3-和 24-5β-胆烷三唑基衍生物，其中含有阴离子结合的三唑鎓位点和疏水性胆烷残基。研究了三唑鎓部分的位置（在 3α-、3β-位）对氟离子络合的影响。研究了一系列无机和有机阴离子的三（三唑鎓）配体的阴离子结合特性，并观察到氟离子、硫酸氢根和苯甲酸根阴离子的高络合常数。
• Sialic acid derivatives
  申请人：Mitsubishi Chemical Corporation

  公开号：US06288041B1

  公开（公告）日：2001-09-11

  Sialic acid derivatives represented by the following general formula: wherein R1 represents a residue of a steroid compound excluding cholestane and cholestene residues, R2 represents hydrogen or methyl group, R3 represents a C1-C6 alkyl group and other, R4 represents hydrogen or acyl group, R5 represents a group of R15O— (R15 represents a C2-C7 acyl group and other), and X represents oxygen or sulfur atom, and their derivatives. These derivatives have activating effect on choline acetyltransferase activity in the chlonergic neurons, and are useful for preventive and therapeutic treatment of dementia, memory disorder, peripheral nervous disorder and so forth.

  以下是通用公式表示的唾液酸衍生物： 其中R1代表类固醇化合物残基，但不包括胆甾烷和胆甾烯残基，R2代表氢或甲基基团，R3代表C1-C6烷基基团和其他，R4代表氢或酰基基团，R5代表R15O—基团（R15代表C2-C7酰基基团和其他），X代表氧或硫原子，以及它们的衍生物。这些衍生物对胆碱乙酰转移酶在胆碱能神经元中的活性具有激活作用，并可用于预防和治疗痴呆症、记忆障碍、外周神经障碍等疾病。
• Cu–Al mixed oxide catalysts for azide–alkyne 1,3-cycloaddition in ethanol–water
  作者：R. González-Olvera、C. I. Urquiza-Castro、G. E. Negrón-Silva、D. Ángeles-Beltrán、L. Lomas-Romero、A. Gutiérrez-Carrillo、V. H. Lara、R. Santillan、J. A. Morales-Serna

  DOI：10.1039/c6ra10097j

  日期：——

  Cu(Al)O mixed oxide promotes the formation of 1,2,3-triazoles from an alkyne–azide cycloaddition reaction with excellent yields using an EtOH–H₂O mixture as the solvent under microwave heating.

  Cu(Al)O混合氧化物促进了在微波加热下使用EtOH-H₂O混合溶剂从炔烃-叠氮基环加成反应中高产率形成1,2,3-三唑的过程。
• Design and synthesis of new carbohydrate-lithocholic acid conjugates linked via 1,2,3-triazole rings
  作者：Claudia I. Bautista-Hernández、Guillermo E. Negrón-Silva、Rosa Santillán、Blanca Ivonne Vergara-Arenas、Deyanira Ángeles-Beltrán、Leticia Lomas-Romero、Diego Pérez-Martínez

  DOI：10.1016/j.tet.2018.03.008

  日期：2018.4

  work, we report the synthesis of a novel carbohydrate-lithocholic acid conjugate linked through of 1,2,3-triazole rings and its derivatives in good to excellent yields. The conjugate was synthesized via copper-catalyzed azide−alkyne cycloaddition (CuAAC) from methyl 4,6-O-benzylidene-2,3-di-O-propargyl-α-d-glucopyranoside and methyl 3-azidolithocholate. The structures of all new compounds were properly

  在这项工作中，我们报告了通过1,2,3-三唑环及其衍生物连接的新型碳水化合物-油胆酸共轭物的合成，收率良好。将缀合物通过从甲基4,6-铜催化的叠氮化物-炔烃环加成加成（CuAAC）合成ø -亚苄基-2,3-二- ö -propargyl-α- d吡喃葡萄糖苷和甲基3- azidolithocholate。所有新化合物的结构均通过红外（IR），高分辨率质谱（HRMS）以及一维和二维核磁共振（NMR）进行了适当表征。
• SIALIC ACID DERIVATIVES
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP0837070A1

  公开（公告）日：1998-04-22

  Sialic acid derivatives represented by the following general formula: wherein R1 represents a residue of a steroid compound excluding cholestane and cholestene residues, R2 represents hydrogen or methyl group, R3 represents a C1-C6 alkyl group and other, R4 represents hydrogen or acyl group, R5 represents a group of R15O- (R15 represents a C2-C7 acyl group and other), and X represents oxygen or sulfur atom, and their derivatives. These derivatives have activating effect on choline acetyltransferase activity in the chlonergic neurons, and are useful for preventive and therapeutic treatment of dementia, memory disorder, peripheral nervous disorder and so forth.

  由以下通式代表的硅烷酸衍生物： 其中 R1 代表类固醇化合物的残基，不包括胆甾烷和胆甾烯残基；R2 代表氢或甲基；R3 代表 C1-C6 烷基及其他；R4 代表氢或酰基；R5 代表 R15O-（R15 代表 C2-C7酰基及其他）；X 代表氧原子或硫原子；以及它们的衍生物。这些衍生物对胆碱能神经元中的胆碱乙酰转移酶活性有激活作用，可用于痴呆、记忆障碍、周围神经紊乱等疾病的预防和治疗。