2',3'-isopropylidene-N6-exo-norbornyladenosine | 103626-24-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-isopropylidene-N6-exo-norbornyladenosine
• 英文别名: ((3aR,4R,6R,6aR)-6-(6-(bicyclo[2.2.1]heptan-2-ylamino)-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol；[(3aR,4R,6R,6aR)-4-[6-(2-bicyclo[2.2.1]heptanylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol
• CAS: 103626-24-0
• 化学式: C₂₀H₂₇N₅O₄
• 分子量: 401.465
• InChiKey: OCGZKNKQXJYSMF-ZXRVYSIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2',3'-isopropylidene-N6-exo-norbornyladenosine 在 硝酸 、 乙酸酐 、 碳酸氢钠 作用下， 以 水 为溶剂， 生成 ((2R,3S,4R,5R)-5-(6-(bicycle-[2,2,1]-heptan-2-ylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methylnitrate
  参考文献：
  名称：

  [EN] METHOD OF REDUCING INTRAOCULAR PRESSURE IN HUMANS
  [FR] PROCÉDÉ DE RÉDUCTION DE LA PRESSION INTRAOCULAIRE CHEZ LES HUMAINS

  摘要：

  本文提供了公式I的化合物，包含有效量的公式I化合物的组合物，以及用于降低眼压的方法，包括向需要的受试者施用公式I化合物的有效量。

  公开号：

  WO2010127210A1
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 N⁶-(endo-norborn-2-yl)adenosine 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以92%的产率得到2',3'-isopropylidene-N6-exo-norbornyladenosine
  参考文献：
  名称：

  N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists

  摘要：

  Adenosines bearing 5'-modification in conjunction with an N-6-substituent have previously been shown to act as partial agonists at the A(1) adenosine receptor. Our current work investigates the effect of modifying the 5'-position in conjunction with efficacious bicyclic and tricyclic N-6-substituents. Several highly potent agonists for the A(1) adenosine receptor were identified; however, all of these compounds behaved as full agonists. In keeping with previous reports, 5'-halogen and 5'-sulfide derivatives of N-6-(endo-norborn-2-yl) adenosine were, in general, low nanomolar agonists of the A(1) adenosine receptor. The known partial agonist, N-6-cyclopentyl-5'-deoxy-5'-ethylthioadenosine (2), also behaved as a full agonist in our assay. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.010

文献信息

• [EN] METHOD OF REDUCING INTRAOCULAR PRESSURE IN HUMANS<br/>[FR] PROCÉDÉ DE RÉDUCTION DE LA PRESSION INTRAOCULAIRE CHEZ LES HUMAINS
  申请人：INOTEK PHARMACEUTICALS CORP

  公开号：WO2010127210A1

  公开（公告）日：2010-11-04

  Provided herein are compounds of Formula I, compositions comprising an effective amount of a compound of Formula I, and methods for reducing intraocular pressure comprising administering an effective amount of compounds of Formula I to a subject in need thereof.

  本文提供了公式I的化合物，包含有效量的公式I化合物的组合物，以及用于降低眼压的方法，包括向需要的受试者施用公式I化合物的有效量。
• US2014/275128
  申请人：——

  公开号：——

  公开（公告）日：——
• N6-bicycloadenosines
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0181128B1

  公开（公告）日：1989-10-04
• [EN] METHODS OF PREVENTING, REDUCING OR TREATING MACULAR DEGENERATION<br/>[FR] PROCÉDÉS DE PRÉVENTION, DE RÉDUCTION OU DE TRAITEMENT DE LA DÉGÉNÉRESCENCE MACULAIRE
  申请人：INOTEK PHARMACEUTICALS CORP

  公开号：WO2016090005A1

  公开（公告）日：2016-06-09

  The present invention is directed to selective adenosine A1 agonist compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat, reduce or prevent age-related macular degeneration.

  本发明涉及选择性腺苷A1激动剂化合物，包括这种化合物的药物组合物，以及使用这种化合物来治疗、减少或预防年龄相关性黄斑变性的方法。
• N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists
  作者：T.D. Ashton、Stephen P. Baker、Sally A. Hutchinson、Peter J. Scammells

  DOI：10.1016/j.bmc.2007.11.010

  日期：2008.2.15

  Adenosines bearing 5'-modification in conjunction with an N-6-substituent have previously been shown to act as partial agonists at the A(1) adenosine receptor. Our current work investigates the effect of modifying the 5'-position in conjunction with efficacious bicyclic and tricyclic N-6-substituents. Several highly potent agonists for the A(1) adenosine receptor were identified; however, all of these compounds behaved as full agonists. In keeping with previous reports, 5'-halogen and 5'-sulfide derivatives of N-6-(endo-norborn-2-yl) adenosine were, in general, low nanomolar agonists of the A(1) adenosine receptor. The known partial agonist, N-6-cyclopentyl-5'-deoxy-5'-ethylthioadenosine (2), also behaved as a full agonist in our assay. (C) 2007 Elsevier Ltd. All rights reserved.