N-butyl-N-methyl-7-(3-isobutyloxycarbonyloxy-17-oxoestra-1,3,5(10)-trien-6α-yl)heptanamide | 925673-21-8

• 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-isobutyloxycarbonyloxy-17-oxoestra-1,3,5(10)-trien-6α-yl)heptanamide
• CAS: 925673-21-8
• 化学式: C₃₅H₅₃NO₅
• 分子量: 567.81
• InChiKey: KDXQFEKUWLVZCQ-GSBCMJOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-butyl-N-methyl-7-(3-isobutyloxycarbonyloxy-17-oxoestra-1,3,5(10)-trien-6α-yl)heptanamide 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 生成 N-butyl-7-[(6S,8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-6-yl]-N-methylheptanamide
  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：

  (17beta)-3,17-二[(四氢-2H-吡喃-2-基)氧基]-雌甾-1,3,5(10)-三烯-6-醇 在 三乙基硅烷 、 jones' reagent 、 三正丁胺 、 三氟化硼乙醚 、 sodium acetate 、 magnesium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 13.0h， 生成 N-butyl-N-methyl-7-(3-isobutyloxycarbonyloxy-17-oxoestra-1,3,5(10)-trien-6α-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