4-nitro-17β-(4'-t-butylbenzenesulfonamido)-1,3,5(10)-estratrien-3-ol

• 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: 4-nitro-17β-(4'-t-butylbenzenesulfonamido)-1,3,5(10)-estratrien-3-ol
• 英文别名: 4-tert-butyl-N-[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-4-nitro-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]benzenesulfonamide
• 化学式: C₂₈H₃₆N₂O₅S
• 分子量: 512.67
• InChiKey: LWAKNLNPYJBOBG-RNRUCVIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(N-乙基-3-甲基-4-亚硝基苯胺基)乙醇 在 吡啶 、 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.2h， 生成 4-nitro-17β-(4'-t-butylbenzenesulfonamido)-1,3,5(10)-estratrien-3-ol
  参考文献：
  名称：

  A-ring substituted 17β-arylsulfonamides of 17β-aminoestra-1,3,5(10)-trien-3-ol as highly potent reversible inhibitors of steroid sulfatase

  摘要：

  Steroid sulfatase (STS) catalyzes the hydrolysis of the sulfate ester group in biologically inactive sulfated steroids to give biologically active steroids. Inhibitors of STS are considered to be potential therapeutics for treating hormone-dependent cancers such as ER+ breast cancer. A series of 4-substituted 17 beta-arylsulfonamides of 17 beta-aminoestra-1,3,5(10)-trien-3-ol were prepared and examined as STS inhibitors. The presence of a NO2 or Br at the 2-position of the A-ring resulted in a decrease in potency compared to their A-ring-unsubstituted counterparts. However the presence of a nitro group or fluorine atom at the 4-position of the A-ring resulted in an increase in potency and one of these compounds exhibited a K-i(app) value of 1 nM. Modeling studies provided insight into how these compounds interact with active site residues. The anti-proliferative activity of the 3'-Br, 3'-CF3, 4-NO2-3'-Br and 4-NO2-3'-CF3 derivatives were examined using the NCI 60-cell-line panel and found to have mean graph midpoint values of 1.9-3.4 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.019