9-{2-[2-(2-aminoethoxy)ethoxy]ethyl}adenine | 176520-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-{2-[2-(2-aminoethoxy)ethoxy]ethyl}adenine
• 英文别名: 9-[2-[2-(2-Aminoethoxy)ethoxy]ethyl]purin-6-amine
• CAS: 176520-28-8
• 化学式: C₁₁H₁₈N₆O₂
• 分子量: 266.303
• InChiKey: XTWVKWFVQWTPSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-hydroxysuccinimide ester of 4-androsten-3-one-17β-carboxylic acid 、 9-{2-[2-(2-aminoethoxy)ethoxy]ethyl}adenine 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以27%的产率得到17β-{[2-(2-[2-(6-amino-9H-purin-9-yl)ethoxy]ethoxy)ethyl]carbamoyl}androst-4-en-3-one
  参考文献：
  名称：

  Progesterone–adenine hybrids as bivalent inhibitors of P-glycoprotein-mediated multidrug efflux: Design, synthesis, characterization and biological evaluation

  摘要：

  Bivalent ligands were designed on the basis of the described close proximity of the ATP-site and the putative steroid-binding site of P-glycoprotein (ABCB1). The syntheses of 19 progesterone-adenine hybrids are described. Their abilities to inhibit P-glycoprotein-mediated daunorubicin efflux in K562/R7 human leukemic cells overexpressing P-glycoprotein were evaluated versus progesterone. The hybrid with a hexamethylene linker chain showed the best inhibitory potency. The efficiency of these progesterone-adenine hybrids depends on two main factors: (i) the nature of the linker and (ii) its attachment point on the steroid skeleton. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.07.010
• 作为产物：
  描述：

  2-(2-(2-azidoethoxy)ethoxy)ethyl methanesulfonate 在 钯 氢气 、 sodium hydride 作用下， 生成 9-{2-[2-(2-aminoethoxy)ethoxy]ethyl}adenine
  参考文献：
  名称：

  Adenine-arginine mimetics as bisubstrate analog inhibitors of cAMP-dependent protein kinase

  摘要：

  Simple bisubstrate analogs, Ad-E1-Gn, Ad-E2-Gn, and Ad-E3-Gn, are designed to be proto-type adenine-arginine mimetic structures. Both Ad-E1-Gn and Ad-E2-Gn inhibit PKA with IC50 values similar to that of adenosine at 100 mu M ATP and are more potent inhibitors than adenosine at physiologically relevant 2 mM ATP. Ad-E3-Gn is 10-fold less potent than the other two analogs. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00140-0