17β-{[trans-4-(6-aminopurin-9-ylmethyl)cyclohexylmethyl]carbamoyl}androst-4-en-3-one | 1233224-79-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17β-{[trans-4-(6-aminopurin-9-ylmethyl)cyclohexylmethyl]carbamoyl}androst-4-en-3-one
• CAS: 1233224-79-7
• 化学式: C₃₃H₄₆N₆O₂
• 分子量: 558.767
• InChiKey: PVSORQXCNXFGEA-KTMYUYISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  41.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  115.79
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  黄体酮 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 4.0h， 生成 17β-{[trans-4-(6-aminopurin-9-ylmethyl)cyclohexylmethyl]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

文献信息

• Design, synthesis and evaluation of progesterone–adenine hybrids as bivalent inhibitors of P-glycoprotein-mediated multidrug efflux
  作者：Waël Zeinyeh、Ghina Alameh、Sylvie Radix、Catherine Grenot、Charles Dumontet、Nadia Walchshofer

  DOI：10.1016/j.bmcl.2010.03.085

  日期：2010.5

  Steroidal bivalent ligands were designed on the basis of the described closer proximity of the ATP-site and the putative steroid-binding site of P-glycoprotein (ABCB1). The syntheses of seven progesterone-adenine hybrids were described. Their abilities to inhibit P-glycoprotein-mediated daunorubicin efflux in K562/R7 human leukemic cells overexpressing P-glycoprotein were evaluated versus progesterone. (C) 2010 Elsevier Ltd. All rights reserved.