N⁶-(1-naphthalenemethyl)-2'-deoxy-2'-aminoadenosine | 287177-09-7

• 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: N⁶-(1-naphthalenemethyl)-2'-deoxy-2'-aminoadenosine
• 英文别名: 2'-amino-2'-deoxy-N⁶-(1-naphthylmethyl)adenosine；(2R,3S,4R,5R)-4-amino-2-(hydroxymethyl)-5-[6-(naphthalen-1-ylmethylamino)purin-9-yl]oxolan-3-ol
• CAS: 287177-09-7
• 化学式: C₂₁H₂₂N₆O₃
• 分子量: 406.444
• InChiKey: WQHLFBUVEDHCMD-BZSOYRFXSA-N

物化性质

• 沸点：
  747.8±70.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  阿司匹林 、 N⁶-(1-naphthalenemethyl)-2'-deoxy-2'-aminoadenosine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N⁶-(1-naphthalenemethyl)-2'-deoxy-2'-(2-acetoxybenzamido)adenosine
  参考文献：
  名称：

  腺苷类似物通过基于结构的药物设计作为锥虫科甘油3-磷酸脱氢酶的选择性抑制剂。

  摘要：

  在我们继续进行基于抗锥虫病药物的结构设计时，寄生虫选择性腺苷类似物被确定为低甘油三磷酸甘油醛脱氢酶（GAPDH）的抑制剂。布鲁氏锥虫，克氏锥虫，墨西哥利什曼原虫和人类GAPDH的晶体结构提供了NAD（+）的腺苷部分如何与蛋白质相互作用的详细信息，这有助于理解一系列腺苷类似物对各种氨基酸的亲和力。 GAPDH。从对铅化合物的萘甲基和苯甲酰胺取代基进行修饰的探索中，N（6）-（1-萘甲基）-2'-脱氧-2'-（3-甲氧基苯甲酰胺基）腺苷（6e），N（6）-（研究了取代的萘甲基）-2'-脱氧-2'-（取代的苯甲酰胺基）腺苷类似物。N（6）-（1-萘甲基）-2'-脱氧-2'-（3,5-二甲氧基苯甲酰胺基）腺苷（6m），N（6）-[1-（3-羟基萘）甲基] -2'-脱氧-2'-（3,5-二甲氧基苯甲酰胺基）腺苷（7m），N（6）-[1-（3-甲氧基萘）甲基] -2'-脱氧-2'-（3,5-二甲氧基苯甲酰胺基）腺苷（

  DOI：

  10.1021/jm000472o
• 作为产物：
  描述：

  阿糖腺苷 在 吡啶 、 四氯化碳 、 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 、 丙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 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

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.
• Adenosine Analogues as Selective Inhibitors of Glyceraldehyde-3-phosphate Dehydrogenase of <i>Trypanosomatidae</i> via Structure-Based Drug Design
  作者：Jerome C. Bressi、Christophe L. M. J. Verlinde、Alex M. Aronov、My Le Shaw、Sam S. Shin、Lisa N. Nguyen、Stephen Suresh、Frederick S. Buckner、Wesley C. Van Voorhis、Irwin D. Kuntz、Wim G. J. Hol、Michael H. Gelb

  DOI：10.1021/jm000472o

  日期：2001.6.1

  N(6)-[1-(3-hydroxynaphthalene)methyl]-2'-deoxy-2'-(3,5-dimethoxybenzamido)adenosine (7m), N(6)-[1-(3-methoxynaphthalene)methyl]-2'-deoxy-2'-(3,5-dimethoxybenzamido)adenosine (9m), N(6)-(2-naphthalenemethyl)-2'-deoxy-2'-(3-methoxybenzamido)adenosine (11e), and N(6)-(2-naphthalenemethyl)-2'-deoxy-2'-(3,5-dimethoxybenzamido)adenosine (11m) demonstrated a 2- to 3-fold improvement over 6e and a 7100- to 25000-fold improvement

  在我们继续进行基于抗锥虫病药物的结构设计时，寄生虫选择性腺苷类似物被确定为低甘油三磷酸甘油醛脱氢酶（GAPDH）的抑制剂。布鲁氏锥虫，克氏锥虫，墨西哥利什曼原虫和人类GAPDH的晶体结构提供了NAD（+）的腺苷部分如何与蛋白质相互作用的详细信息，这有助于理解一系列腺苷类似物对各种氨基酸的亲和力。 GAPDH。从对铅化合物的萘甲基和苯甲酰胺取代基进行修饰的探索中，N（6）-（1-萘甲基）-2'-脱氧-2'-（3-甲氧基苯甲酰胺基）腺苷（6e），N（6）-（研究了取代的萘甲基）-2'-脱氧-2'-（取代的苯甲酰胺基）腺苷类似物。N（6）-（1-萘甲基）-2'-脱氧-2'-（3,5-二甲氧基苯甲酰胺基）腺苷（6m），N（6）-[1-（3-羟基萘）甲基] -2'-脱氧-2'-（3,5-二甲氧基苯甲酰胺基）腺苷（7m），N（6）-[1-（3-甲氧基萘）甲基] -2'-脱氧-2'-（3,5-二甲氧基苯甲酰胺基）腺苷（
• 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.