2-chloroadenosine-5'-N-methyl uronamide | 127258-30-4

• 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-chloroadenosine-5'-N-methyl uronamide
• 英文别名: 2-chloro-5'-methylcarboxamidoadenosine；(2S,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• CAS: 127258-30-4
• 化学式: C₁₁H₁₃ClN₆O₄
• 分子量: 328.715
• InChiKey: QAIIGSHVSKGYFL-LKCKTBJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氯腺嘌呤核苷 在 盐酸 、 氢氧化钾 、 potassium permanganate 、 氯化亚砜 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 91.0h， 生成 2-chloroadenosine-5'-N-methyl uronamide
  参考文献：
  名称：

  2-(Arylalkylamino)adenosin-5'-uronamides: a new class of highly selective adenosine A2 receptor ligands

  摘要：

  The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)-adenosin-5'-uronamides is described. Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor subtype on the basis of rat brain receptor binding. The general structure-activity relationship of this series of compounds is discussed both in terms of potency at A2 receptors as well as receptor subtype selectivity. It is possible to introduce a hydrophilic carboxyalkyl substituent to this series such as in CGS 21680A (3h) and still retain good potency and selectivity for A2 receptors. In addition, functional data in a perfused working rat heart model shows that these compounds possess full agonist properties at A2 receptors with 3h having a greater than 1500-fold separation between A2 (coronary vasodilatory) and A1 (negative chronotropic) receptor mediated events.

  DOI：

  10.1021/jm00169a015

文献信息

• An efficient convergent synthesis of adenosine-5′-N-alkyluronamides
  作者：Shane M. Devine、Peter J. Scammells

  DOI：10.1016/j.tet.2007.11.100

  日期：2008.2

  Herein we report an efficient synthesis of adenosine-5'-N-alkyluronamides in which an enzyme-mediated deacetylation reaction is a key to the selective modification of the 5'-N-position, prior to coupling the ribose and purine components via a microwave-assisted Vorbruggen coupling. This approach provides access to highly functionalised adenosines with 2- and N-6-substitutents, which can be incorporated before or after the ribose-coupling step. In all cases the microwave-assisted Vorbruggen coupling conditions afforded anomerically pure purine ribosides in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.
• HUTCHISON, ALAN J.;WILLIAMS, MICHAEL;JESUS, REYNALDA DE;RINA, YOKOYAMA;OE+, J. MED. CHEM., 33,(1990) N, C. 1919-1924
  作者：HUTCHISON, ALAN J.、WILLIAMS, MICHAEL、JESUS, REYNALDA DE、RINA, YOKOYAMA、OE+

  DOI：——

  日期：——
• 2-(Arylalkylamino)adenosin-5'-uronamides: a new class of highly selective adenosine A2 receptor ligands
  作者：Alan J. Hutchison、Michael Williams、Reynalda De Jesus、Rina Yokoyama、Howard H. Oei、Geetha R. Ghai、Randy L. Webb、Harry C. Zoganas、George A. Stone、Michael F. Jarvis

  DOI：10.1021/jm00169a015

  日期：1990.7

  The synthesis and receptor-binding profiles at adenosine receptor subtypes for a series of 2-(arylalkylamino)-adenosin-5'-uronamides is described. Halogenated 2-phenethylamino analogues such as 3e show greater than 200-fold selectivity for the A2 receptor subtype on the basis of rat brain receptor binding. The general structure-activity relationship of this series of compounds is discussed both in terms of potency at A2 receptors as well as receptor subtype selectivity. It is possible to introduce a hydrophilic carboxyalkyl substituent to this series such as in CGS 21680A (3h) and still retain good potency and selectivity for A2 receptors. In addition, functional data in a perfused working rat heart model shows that these compounds possess full agonist properties at A2 receptors with 3h having a greater than 1500-fold separation between A2 (coronary vasodilatory) and A1 (negative chronotropic) receptor mediated events.