(1R,3R,4R,7S)-7-benzyloxy-1-methansulfonyloxymethyl-3-(N6-benzoyladenin-9-yl)-2-oxa-5-aza-bicyclo[2.2.1]heptane | 938055-77-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1R,3R,4R,7S)-7-benzyloxy-1-methansulfonyloxymethyl-3-(N6-benzoyladenin-9-yl)-2-oxa-5-aza-bicyclo[2.2.1]heptane
• 英文别名: [(1R,3R,4R,7S)-3-(6-benzamidopurin-9-yl)-7-phenylmethoxy-2-oxa-5-azabicyclo[2.2.1]heptan-1-yl]methyl methanesulfonate
• CAS: 938055-77-7
• 化学式: C₂₆H₂₆N₆O₆S
• 分子量: 550.595
• InChiKey: WHOOSXPWBUPBQP-WFAUAPPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,7S)-7-benzyloxy-1-methansulfonyloxymethyl-3-(N6-benzoyladenin-9-yl)-2-oxa-5-aza-bicyclo[2.2.1]heptane 在 palladium dihydroxide 氨 、 ammonium formate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 (1R,3R,4R,7S)-3-(6-amino-purin-9-yl)-1-hydroxymethyl-2-oxa-5-aza-bicyclo[2.2.1]heptan-7-ol
  参考文献：
  名称：

  Synthesis of 2′-Amino-LNA Purine Nucleosides

  摘要：

  The first reported synthesis of 2'-amino-LNA purine nucleosides via a transnucleosidation is accomplished enabling the preparation of oligonucleotides incorporating 2'-amino-LNA with all four natural bases.

  DOI：

  10.1080/15257770600793729
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 苯磺酰胺 、 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 生成 (1R,3R,4R,7S)-7-benzyloxy-1-methansulfonyloxymethyl-3-(N6-benzoyladenin-9-yl)-2-oxa-5-aza-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis of 2′-Amino-LNA Purine Nucleosides

  摘要：

  The first reported synthesis of 2'-amino-LNA purine nucleosides via a transnucleosidation is accomplished enabling the preparation of oligonucleotides incorporating 2'-amino-LNA with all four natural bases.

  DOI：

  10.1080/15257770600793729

文献信息

• Design, synthesis, and biological evaluation of LNA nucleosides as adenosine A3 receptor ligands
  作者：Jacob Ravn、Katrine Qvortrup、Christoph Rosenbohm、Troels Koch

  DOI：10.1016/j.bmc.2007.05.056

  日期：2007.8

  on the bicyclo[2.2.1]heptane scaffold of locked nucleic acid (LNA) and tested them for both agonist and antagonist activity at the adenosine A(3) receptor. The design of these derivatives was based on the known A(3) agonist IB-MECA and related compounds. Modifications thus include the 5'-uronamides and N(6)-(3-iodobenzyl) derivatives. In this way we have prepared analogs of known A(3) agonists with

  我们基于锁定核酸（LNA）的双环[2.2.1]庚烷骨架制备了一系列腺苷类似物，并对其在腺苷A（3）受体上的激动剂和拮抗剂活性进行了测试。这些衍生物的设计基于已知的A（3）激动剂IB-MECA和相关化合物。因此，修饰包括5'-脲酰胺和N（6）-（3-碘苄基）衍生物。以这种方式，我们制备了已知的A（3）激动剂的类似物，其中糖环被限制在N-构象中。为了比较，我们还制备了IB-MECA的2'-O-甲基衍生物。LNA核苷无激动剂活性，但其中一些是有效的拮抗剂。IB-MECA的2'-O-甲基衍生物是与母体化合物具有相似效力的激动剂。
• Adenosine Receptor Antagonists
  申请人：Ravn Jacob

  公开号：US20100062994A1

  公开（公告）日：2010-03-11

  The present application discloses locked nucleoside compounds of the Formula I which act as antagonists of adenosine receptors, in particular the adenosine A3 receptor, and the use of such adenosine A3 receptor compounds in medicine, e.g. for the treatment or alleviation or prophylaxis of selected from the group consisting of pain; inflammatory diseases, arthritis, multiple sclerosis, inflammation, asthma and psoriasis; gastro-intestinal disorders; allergy; disorders associated with mast cell or eosinophil activation and degranulation; cardio-vascular disorders; cutaneous diseases; wound healing; opthalmological disorders; respiratory disorders; kidney diseases; central nervous system disorders; Alzheimer's disease, Creutzfeldt-Jacob disease, Huntington's disease and Parkinson's disease; trauma and seizure; diabetes; osteoporosis; diseases of the immune system; cancers, infections; high blood pressure, locomotor hyperactivity, hypertension and depression; acute hypoxia; neonatal hypoxia, hypoxia and chronic hypoxia; and infertility.

  本申请披露了Formula I的锁定核苷酸化合物，这些化合物作为腺苷受体的拮抗剂，特别是腺苷A3受体，并且披露了这种腺苷A3受体化合物在医学中的用途，例如用于治疗或缓解或预防以下疾病：疼痛；炎症性疾病，关节炎，多发性硬化症，炎症，哮喘和银屑病；胃肠道疾病；过敏；与肥大细胞或嗜酸性粒细胞活化和脱颗粒相关的疾病；心血管疾病；皮肤疾病；创伤愈合；眼科疾病；呼吸系统疾病；肾脏疾病；中枢神经系统疾病；阿尔茨海默病，克雅氏病，亨廷顿病和帕金森病；创伤和癫痫发作；糖尿病；骨质疏松；免疫系统疾病；癌症，感染；高血压，运动过度，高血压和抑郁症；急性缺氧；新生儿缺氧，缺氧和慢性缺氧；以及不育症。
• WO2008/6369
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of 2′-Amino-LNA Purine Nucleosides
  作者：Jacob Ravn、Christoph Rosenbohm、Signe M. Christensen、Troels Koch

  DOI：10.1080/15257770600793729

  日期：2006.9

  The first reported synthesis of 2'-amino-LNA purine nucleosides via a transnucleosidation is accomplished enabling the preparation of oligonucleotides incorporating 2'-amino-LNA with all four natural bases.