2'-azido-6-chloro-2'-deoxyadenosine | 287177-06-4

• 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'-azido-6-chloro-2'-deoxyadenosine
• 英文别名: (2R,3S,4R,5R)-4-azido-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 287177-06-4
• 化学式: C₁₀H₁₀ClN₇O₃
• 分子量: 311.688
• InChiKey: SZZIRXIDVYUCEA-QYYRPYCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-azido-6-chloro-2'-deoxyadenosine 以 丙醇 为溶剂， 反应 16.0h， 生成 N⁶-(1-naphthalenemethyl)-2'-deoxy-2'-aminoadenosine
  参考文献：
  名称：

  Improving an antitrypanosomal lead applying nucleophilic substitution on a safety catch linker

  摘要：

  In a joint effort with various laboratories we have been aiming at the structure-based design of glycolysis inhibitors as anti-trypanosomal drugs. 2'-Deoxy-2-(3-methoxybenzamido)-N-6-(1-naphtylmethyl)adenosine (1a) was thus revealed as a promising lead structure for the development of selective agents against protozoan parasites. Here we describe the polymer-assisted synthesis of novel amido derivatives of the scaffold 2-amino-2'-deoxy-N-6-(1-naphtylmethyl)adenosine (5a) we reported recently. This building block synthesized in solution was treated with an excess of polymer-supported carboxylic acids leading to chemoselective, practically quantitative conversion of the amine to the desired analogous amides. The best compound (1h) from this series was obtained after on-bead nucleophilic substitution of the carboxylic acid equivalent attached to the Kenner safety catch linker and exhibited an improved inhibitory effect on T. b. brucei blood stream forms with an IC50 of 0.85 muM in vitro (C) 2001 Elsevier Science. Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00253-x
• 作为产物：
  描述：

  阿糖腺苷 在 4-二甲氨基吡啶 、 sodium azide 、 四丁基氟化铵 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 吡啶 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 2'-azido-6-chloro-2'-deoxyadenosine
  参考文献：
  名称：

  2′-Amino-2′-deoxy-N6-(1-naphthylmethyl)adenosine as Novel Scaffold for a Polymer-Assisted Amidation Protocol

  摘要：

  The synthesis of a novel scaffold for the simple and high-yielding polymer-assisted solution phase preparation of arrays of 2'-amido-2'-deoxy-N-6-(1-naphthylmethyl)adenosine derivatives 10a-h as analogues of a known inhibitor of trypanosomatid glycosomal glyceraldehyde-3-phosphate dehydrogenase is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00228-3

文献信息

• 2′-Amino-2′-deoxy-N6-(1-naphthylmethyl)adenosine as Novel Scaffold for a Polymer-Assisted Amidation Protocol
  作者：Abolfasl Golisade、Serge Van Calenbergh、Andreas Link

  DOI：10.1016/s0040-4020(00)00228-3

  日期：2000.5

  The synthesis of a novel scaffold for the simple and high-yielding polymer-assisted solution phase preparation of arrays of 2'-amido-2'-deoxy-N-6-(1-naphthylmethyl)adenosine derivatives 10a-h as analogues of a known inhibitor of trypanosomatid glycosomal glyceraldehyde-3-phosphate dehydrogenase is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Improving an antitrypanosomal lead applying nucleophilic substitution on a safety catch linker
  作者：Abolfasl Golisade、Claudia Herforth、Ludo Quirijnen、Louis Maes、Andreas Link

  DOI：10.1016/s0968-0896(01)00253-x

  日期：2002.1

  In a joint effort with various laboratories we have been aiming at the structure-based design of glycolysis inhibitors as anti-trypanosomal drugs. 2'-Deoxy-2-(3-methoxybenzamido)-N-6-(1-naphtylmethyl)adenosine (1a) was thus revealed as a promising lead structure for the development of selective agents against protozoan parasites. Here we describe the polymer-assisted synthesis of novel amido derivatives of the scaffold 2-amino-2'-deoxy-N-6-(1-naphtylmethyl)adenosine (5a) we reported recently. This building block synthesized in solution was treated with an excess of polymer-supported carboxylic acids leading to chemoselective, practically quantitative conversion of the amine to the desired analogous amides. The best compound (1h) from this series was obtained after on-bead nucleophilic substitution of the carboxylic acid equivalent attached to the Kenner safety catch linker and exhibited an improved inhibitory effect on T. b. brucei blood stream forms with an IC50 of 0.85 muM in vitro (C) 2001 Elsevier Science. Ltd. All rights reserved.