3β-azido-5α-cholestane | 14602-53-0

• 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-5α-cholestane
• 英文别名: 3β-Azido-5α-cholestan；(3S,5S,8R,9S,10S,13R,14S,17R)-3-azido-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 14602-53-0
• 化学式: C₂₇H₄₇N₃
• 分子量: 413.69
• InChiKey: ZHFDHSQBXHWICF-QCYZZNICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-azido-5α-cholestane 在 lithium hydroxide 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.0h， 生成 N-{[(3-[(tert-butoxycarbonyl)(cholestan-3-yl)amino]propyl)amino]carbonyl}-β-alanine
  参考文献：
  名称：

  A Synthetic Mimic of Human Fc Receptors:  Defined Chemical Modification of Cell Surfaces Enables Efficient Endocytic Uptake of Human Immunoglobulin-G

  摘要：

  Binding of ligands to macromolecular receptors on the surface of mammalian cells often results in ligand uptake through receptor-mediated endocytosis. Certain human leukocytes and epithelial cells express Fc receptors (FcRs) that bind and internalize antibodies through this mechanism. To mimic this process, we synthesized an artificial FcR comprising the membrane anchor N-alkyl-3 beta-amino-5 alpha-cholestane linked to a disulfide-constrained cyclic peptide, termed FcIII, known to exhibit high affinity and specificity for the Fc region of human IgG. Treatment of human Jurkat lymphocytes that lack natural FcRs with the synthetic FcR (1 mu M, 1 h) installed an average of similar to 6.2 x 10(5) synthetic receptor molecules per cell surface. These treated cells gained the capacity to internalize human IgG at levels greater than human THP-1 cells that express the natural receptors Fc gamma RI and Fc gamma RII. By linking binding motifs for circulating ligands to membrane anchors that cycle between the cell surface and intracellular endosomes, minimalistic cell surface receptors can be used to destroy targeted ligands by endocytosis. These small mimics of macromolecular receptors may be useful for controlling the extracellular abundance of ligands involved in disease.

  DOI：

  10.1021/ja062377w
• 作为产物：
  描述：

  5α（H）-Cholestan-3α醇 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 生成 3β-azido-5α-cholestane
  参考文献：
  名称：

  与有机磷化合物的反应。XLII。与三苯基膦/偶氮二羧酸酯的帮助hydroxysteroids亲核取代†往最‡

  摘要：

  三苯基膦/偶氮二羧酸二乙酯对羟基类固醇的亲核取代反应

  DOI：

  10.1002/hlca.19770600213

文献信息

• [EN] SHIP INHIBITION TO COMBAT OBESITY<br/>[FR] INHIBITION DE SHIP DANS LE CADRE DE LA LUTTE CONTRE L'OBÉSITÉ
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2015003003A1

  公开（公告）日：2015-01-08

  The present invention relates to the use of SHIP1 inhibitors and pan-SHIP1/2 inhibitors in various methods, including, without limitation: (i) a method to treat obesity or reduce body fat of an obese subject; (ii) a method to limit bone development in a subject suffering from an osteopetrotic or sclerotic disease; (iii) a method to treat or prevent diabetes; (iv) a method to reduce glucose intolerance or insulin resistance; and (v) a method to lower cholesterol.

  本发明涉及在各种方法中使用SHIP1抑制剂和全SHIP1/2抑制剂，包括但不限于：(i) 一种治疗肥胖或减少肥胖患者体脂的方法；(ii) 一种限制骨发育的方法，适用于患有骨质增生病或硬化疾病的患者；(iii) 一种治疗或预防糖尿病的方法；(iv) 一种减少葡萄糖耐量或胰岛素抵抗的方法；以及(v) 一种降低胆固醇的方法。
• [EN] METHODS OF ACTIVATING MICROGLIAL CELLS<br/>[FR] PROCÉDÉS D'ACTIVATION DE CELLULES MICROGLIALES
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2020028552A1

  公开（公告）日：2020-02-06

  The present disclosure provides methods of using compositions that inhibit SH2-containing inositol 5'-phosphatases (SHIPs) for activating microglial cells, as well as methods for using such compositions for treatment or ameliorating of neurodegenerative disorders in a subject.

  本公开提供了使用抑制SH2含有肌醇5'-磷酸酯酶（SHIPs）的组合物来激活微胶质细胞的方法，以及利用这些组合物治疗或改善受试者神经退行性疾病的方法。
• Mitsunobu reactions with methanesulfonic acid; The replacement of equatorial hydroxyl groups by azide with net retention of configuration
  作者：Anthony P. Davis、Stephan Dresen、Laurence J. Lawless

  DOI：10.1016/s0040-4039(97)00886-1

  日期：1997.6

  of equatorial cyclohexanols with Ph3P/DEAD/MsOH gives clean conversion to the axial mesylates. Subsequent reaction with NaN3 gives the equatorial azides in overall yields of 74–87%. Axial hydroxyl groups are not affected, allowing the regioselective conversion of methyl cholate into a 3α-azidodiol intermediate for steroid-based synthetic receptors.

  用Ph 3 P / DEAD / MsOH处理赤道环己醇可将其干净地转化为轴向甲磺酸酯。随后与NaN 3的反应使赤道叠氮化物的总产率为74-87％。轴向羟基不受影响，允许胆甾醇将区域选择性地转化为基于类固醇的合成受体的3α-叠氮二醇中间体。
• Nicotinoyl Azide (NCA)-Mediated Mitsunobu Reaction: An Expedient One-Pot Transformation of Alcohols into Azides
  作者：Gianluca Papeo、Helena Posteri、Paola Vianello、Mario Varasi

  DOI：10.1055/s-2004-831254

  日期：——

  A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.

  描述了一种实用而简便的方法，允许从醇类制备叠氮化合物。该过程涉及氧膦型活化，并基于使用烟酰叠氮（NCA），这是一种廉价且易于获得的叠氮离子源。
• Synthesis and anti-HIV activity of cosalane analogues incorporating nitrogen in the linker chain
  作者：Agustin Casimiro-Garcia、Erik De Clercq、Christophe Pannecouque、Myriam Witvrouw、Tracy L. Stup、Jim A. Turpin、Robert W. Buckheit、Mark Cushman

  DOI：10.1016/s0968-0896(99)00269-2

  日期：2000.1

  Introduction of an amido group or an amino moiety into the alkenyl linker chain of cosalane (1) provided a new series of analogues 3-8. The new compounds were evaluated as inhibitors of the cytopathic effect of HIV-1 and HIV-2 in cell culture. The replacement of the 1' and 2' carbons in the linker chain of I by an amido group was generally tolerated. The length of the linker chain and the stereochemistry

  将氨基或氨基部分引入到al草烷（1）的烯基连接链中提供了一系列新的类似物3-8。新化合物被评估为在细胞培养物中抑制HIV-1和HIV-2的细胞病变作用。通常容许I的连接链中的1'和2'碳被酰胺基取代。连接链的长度和甾族环C-3处取代基的立体化学对抗病毒活性和效价都有重要影响。将氨基部分结合到接头中完全消除了抗HIV活性。在HIV复制周期中有几个步骤被提议作为治疗剂开发的目标（De Clercq，EJ Med。Chem。1995，38，2491; De Clercq，E.Pure Appl.Chem。1998，70， 567）。然而，当前批准的抗HIV药物仅针对病毒酶逆转录酶或蛋白酶（Carpenter。CCJ; MA菲斯切尔; SM汉默; Hirsch女士; DM雅各布森; DA; Katzenstein; JSG Montaner; DD里奇曼;密苏里州萨格（Saag）;密歇根州Scho