estrone-3-((+)-10-camphor)sulfonate

• 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: estrone-3-((+)-10-camphor)sulfonate
• 英文别名: [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] [(1R,4S)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonate
• 化学式: C₂₈H₃₆O₅S
• 分子量: 484.657
• InChiKey: QXJUIAKSGWIQHX-FIPQVFAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  雌酚酮 、 左旋樟脑-10-磺酰氯 在 吡啶 作用下， 以100%的产率得到estrone-3-((+)-10-camphor)sulfonate
  参考文献：
  名称：

  Estrone sulfonates as inhibitors of estrone sulfatase

  摘要：

  In our continuing quest to design efficient inhibitors of estrone sulfatase activity and to assess the recognition of estrone sulfate surrogates by estrone sulfatase, we synthesized and evaluated several sulfonate derivatives of 5,6,7,8-tetrahydronaphth-2-ol and estrone. 5,6,7, 8-Tetrahydronaphth-2-methanesulfonate (II), and 5,6,7, 8-tetra-hydronaphth-2-(p-toluene)sulfonate (12) were found not to inhibit estrone sulfatase activity; estrone-3-methane-sulfonate (5), estrone-3-ethanesulfonate (6), estrone-3-butanesulfonate (7), and estrone-3-[(+)10-camphor]sulfonate (8) all weakly inhibited estrone sulfatase, and the best inhibitor from this class of compounds, was estrone-3-(p-toluene)sulfonate (9). At 10 mu M, it inhibited estrone sulfatase activity by 91%. These results emphasize some of the requirements needed for high-affinity binding to the enzyme. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00243-7

文献信息

• Estrone sulfonates as inhibitors of estrone sulfatase
  作者：Nicola M. Howarth、Atul Purohit、Michael J. Reed、Barry V.L. Potter

  DOI：10.1016/s0039-128x(96)00243-7

  日期：1997.4

  In our continuing quest to design efficient inhibitors of estrone sulfatase activity and to assess the recognition of estrone sulfate surrogates by estrone sulfatase, we synthesized and evaluated several sulfonate derivatives of 5,6,7,8-tetrahydronaphth-2-ol and estrone. 5,6,7, 8-Tetrahydronaphth-2-methanesulfonate (II), and 5,6,7, 8-tetra-hydronaphth-2-(p-toluene)sulfonate (12) were found not to inhibit estrone sulfatase activity; estrone-3-methane-sulfonate (5), estrone-3-ethanesulfonate (6), estrone-3-butanesulfonate (7), and estrone-3-[(+)10-camphor]sulfonate (8) all weakly inhibited estrone sulfatase, and the best inhibitor from this class of compounds, was estrone-3-(p-toluene)sulfonate (9). At 10 mu M, it inhibited estrone sulfatase activity by 91%. These results emphasize some of the requirements needed for high-affinity binding to the enzyme. (C) 1997 by Elsevier Science Inc.