N-hydroxysuccinimide ester of 4-androsten-3-one-17β-carboxylic acid | 98653-71-5

• 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: N-hydroxysuccinimide ester of 4-androsten-3-one-17β-carboxylic acid
• 英文别名: androst-4-en-3-one-17β-carboxylic acid succinimidyl ester
• CAS: 98653-71-5
• 化学式: C₂₄H₃₁NO₅
• 分子量: 413.514
• InChiKey: DUNODYSBFDWTJU-NYFVWMHYSA-N

物化性质

• 沸点：
  551.9±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  80.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  9-(4-aminobutyl)-9H-purin-6-amine 、 N-hydroxysuccinimide ester of 4-androsten-3-one-17β-carboxylic acid 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到17β-[(4-(6-aminopurin-9-yl)butyl)carbamoyl]androst-4-en-3-one
  参考文献：
  名称：

  Design, synthesis and evaluation of progesterone–adenine hybrids as bivalent inhibitors of P-glycoprotein-mediated multidrug efflux

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.03.085
• 作为产物：
  描述：

  黄体酮 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 N-hydroxysuccinimide ester of 4-androsten-3-one-17β-carboxylic acid
  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

• Synthesis and evaluation of potential radioligands for the progesterone receptor
  作者：R. M. Hoyte、W. Rosner、I. S. Johnson、J. Zielinski、R. B. Hochberg

  DOI：10.1021/jm00149a027

  日期：1985.11

  Several steroidal analogues were synthesized as potential gamma-emitting radioligands for the progesterone receptor. Each of these compounds was tested as an inhibitor of the specific binding of [3H]-17 alpha,21-dimethyl-19-nor-4,9-pregnadiene-3,20-dione (R5020) to the progesterone receptor in rabbit uterine cytosol. R5020 is a well-known progestin with high affinity for the receptor. Of the compounds synthesized, aromatic N-substituted C-17 steroidal carboxamides inhibited the binding only poorly. Three compounds, 16 alpha-iodo-4-estren-17 beta-ol-3-one, 17 alpha-[2(E)-iodovinyl]-4-estren-17 beta-ol-3-one, and 17 alpha-[2(Z)-iodovinyl]-4-estren-17 beta-ol-3-one were excellent competitors, each having a Ki less than or equal to that of the natural progestin, progesterone. Since similar iodinated analogues of estrogens have been shown to be extremely stable both in vivo and in vitro, these compounds are potentially useful ligands for the progesterone receptor.