N-butyl-N-methyl-7-(3-benzyloxy-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide | 925673-27-4

• 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-butyl-N-methyl-7-(3-benzyloxy-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide
• CAS: 925673-27-4
• 化学式: C₃₇H₅₁NO₃
• 分子量: 557.817
• InChiKey: WZVGPLFYLAASMX-XINKKOELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-butyl-N-methyl-7-(3-benzyloxy-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide 在 sodium tetrahydroborate 、 copper(l) iodide 、 15-冠醚-5 、 碘 、 silver trifluoroacetate 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 N-butyl-N-methyl-7-(3-benzyloxy-17β-hydroxy-2-methoxyestra-1,3,5(10)-trien-6β-yl)heptanamide
  参考文献：
  名称：

  C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation

  摘要：

  A series of estrone and estradiol derivatives having an N-butyl,methyl heptanamide side chain at C6-position were synthesized, tested as inhibitors of type 1 17 beta-HSD and assessed for their possible estrogenic activity. A better type I 17 beta-HSD inhibition was obtained for the 6 beta-side chain orientation over 6 alpha; the C17-alcohols are more potent inhibitors than the corresponding ketones; introducing a 2-methoxy group decreased the inhibitory potency; and the replacement of a C-S bond by a C-C bond in the C6 beta-side chain is not detrimental to inhibition. Interestingly, the new inhibitors were also found less estrogenic than the lead compound in two breast cancer cell lines, T-47D and MCF-7. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.055
• 作为产物：
  描述：

  甲基丁胺 在 三正丁胺 、 potassium carbonate 、 caesium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 9.17h， 生成 N-butyl-N-methyl-7-(3-benzyloxy-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide
  参考文献：
  名称：

  C6-(N,N-butyl-methyl-heptanamide) derivatives of estrone and estradiol as inhibitors of type 1 17β-hydroxysteroid dehydrogenase: Chemical synthesis and biological evaluation

  摘要：

  A series of estrone and estradiol derivatives having an N-butyl,methyl heptanamide side chain at C6-position were synthesized, tested as inhibitors of type 1 17 beta-HSD and assessed for their possible estrogenic activity. A better type I 17 beta-HSD inhibition was obtained for the 6 beta-side chain orientation over 6 alpha; the C17-alcohols are more potent inhibitors than the corresponding ketones; introducing a 2-methoxy group decreased the inhibitory potency; and the replacement of a C-S bond by a C-C bond in the C6 beta-side chain is not detrimental to inhibition. Interestingly, the new inhibitors were also found less estrogenic than the lead compound in two breast cancer cell lines, T-47D and MCF-7. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.055