3-(2-(dimethylamino)ethoxy)-13-methyl-2-nitro-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol | 1618093-36-9

• 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: 3-(2-(dimethylamino)ethoxy)-13-methyl-2-nitro-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
• 英文别名: (8R,9S,13S,14S,17S)-3-[2-(dimethylamino)ethoxy]-13-methyl-2-nitro-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 1618093-36-9
• 化学式: C₂₂H₃₂N₂O₄
• 分子量: 388.507
• InChiKey: KWNAVKGVTDFJCD-HIFDQRORSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  535.0±50.0 °C(predicted)
• 密度：
  1.188±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  雌二醇 在 potassium carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 2.0h， 生成 3-(2-(dimethylamino)ethoxy)-13-methyl-2-nitro-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Bismuth nitrate-induced novel nitration of estradiol: An entry to new anticancer agents

  摘要：

  Direct nitration of estradiol was carried out using metal nitrates on solid surfaces under mild condition, and a combination of bismuth nitrate pentahydrate impregnated KSF clay was found to be the best reagent to synthesize 2- and 4-nitroestradiol effectively. Furthermore, various basic side chains were introduced, through O-linker at C-3, to these nitroestradiols. The ability of these derivatives to cause cytotoxicity in Estrogen Receptor (ER)-positive and ER-negative breast cancer cell lines, as well as cancer cell lines of other origins, was examined. Qualitative structure activity relationship (SAR) has also been studied. We found that a basic side chain containing either a piperidine or morpholine ring, when conjugated to 2-nitroestradiol, was particularly effective at causing cytotoxicity in each of the cancer cell lines examined. Surprisingly, this effective cytotoxicity was even seen in ER-negative breast cancer cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.06.010

文献信息

• Bismuth nitrate-induced novel nitration of estradiol: An entry to new anticancer agents
  作者：Debasish Bandyopadhyay、Gildardo Rivera、Jorge L. Sanchez、Jesse Rivera、Jose C. Granados、Adrian M. Guerrero、Fang-Mei Chang、Robert K. Dearth、John D. Short、Bimal K. Banik

  DOI：10.1016/j.ejmech.2014.06.010

  日期：2014.7

  Direct nitration of estradiol was carried out using metal nitrates on solid surfaces under mild condition, and a combination of bismuth nitrate pentahydrate impregnated KSF clay was found to be the best reagent to synthesize 2- and 4-nitroestradiol effectively. Furthermore, various basic side chains were introduced, through O-linker at C-3, to these nitroestradiols. The ability of these derivatives to cause cytotoxicity in Estrogen Receptor (ER)-positive and ER-negative breast cancer cell lines, as well as cancer cell lines of other origins, was examined. Qualitative structure activity relationship (SAR) has also been studied. We found that a basic side chain containing either a piperidine or morpholine ring, when conjugated to 2-nitroestradiol, was particularly effective at causing cytotoxicity in each of the cancer cell lines examined. Surprisingly, this effective cytotoxicity was even seen in ER-negative breast cancer cells. (C) 2014 Elsevier Masson SAS. All rights reserved.