2-(3,17β-dibenzyloxyestra-1,3,5(10)-trien-11β-yl)ethyl toluenesulfonate | 849241-44-7

• 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: 2-(3,17β-dibenzyloxyestra-1,3,5(10)-trien-11β-yl)ethyl toluenesulfonate
• CAS: 849241-44-7
• 化学式: C₄₁H₄₆O₅S
• 分子量: 650.879
• InChiKey: IXRHNVZOFQXUJK-ZLFFSVFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.04
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(3,17β-dibenzyloxyestra-1,3,5(10)-trien-11β-yl)ethyl toluenesulfonate 在 palladium on activated charcoal 18-冠醚-6 、 氢气 、 potassium hydride 作用下， 以 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 26.17h， 生成 11β-(2-(2-fluoroethoxy)ethyl)estra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  Nonpolar and Short Side Chain Groups at C-11β of Estradiol Result in Antiestrogens

  摘要：

  We have previously found that esters of 11beta-estradiol carboxylates are transformed from an estrogen into an antiestrogen when the 11beta-side chain is increased in length from four to five non-hydrogen atoms (n greater than or equal to 5). To understand the structural requirements for this transformation and obtain metabolically stable analogues that are not susceptible to esterase cleavage, we have synthesized other compounds having an 11beta-side chain composed of other functional groups: ketones, amides, ethers, and thiono esters. With the exception of amides, which bind poorly to the estrogen receptor (ER), all of these compounds exhibit antiestrogenic action when the side chain length is n greater than or equal to 5. Ethers (n greater than or equal to 5), studied in more detail, inhibit the action of estradiol with either ERalpha or ERbeta. In rat uteri they are estrogen antagonists/weak agonists and decrease the concentration of cholesterol in blood (an hepatic estrogenic action). Thus, these short chain and nonpolar 11beta-analogues of estradiol have tissue specific antiestrogenic/estrogenic actions, characteristics of selective estrogen receptor modulators.

  DOI：

  10.1021/jm049352x
• 作为产物：
  描述：

  11β-(1-ethenyl)estra-1,3,5(10)-triene-3,17β-diol 3,17-bis(benzyl ether) 在 吡啶 、 锂硼氢 、 儿萘酚硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 171.0h， 生成 2-(3,17β-dibenzyloxyestra-1,3,5(10)-trien-11β-yl)ethyl toluenesulfonate
  参考文献：
  名称：

  Nonpolar and Short Side Chain Groups at C-11β of Estradiol Result in Antiestrogens

  摘要：

  We have previously found that esters of 11beta-estradiol carboxylates are transformed from an estrogen into an antiestrogen when the 11beta-side chain is increased in length from four to five non-hydrogen atoms (n greater than or equal to 5). To understand the structural requirements for this transformation and obtain metabolically stable analogues that are not susceptible to esterase cleavage, we have synthesized other compounds having an 11beta-side chain composed of other functional groups: ketones, amides, ethers, and thiono esters. With the exception of amides, which bind poorly to the estrogen receptor (ER), all of these compounds exhibit antiestrogenic action when the side chain length is n greater than or equal to 5. Ethers (n greater than or equal to 5), studied in more detail, inhibit the action of estradiol with either ERalpha or ERbeta. In rat uteri they are estrogen antagonists/weak agonists and decrease the concentration of cholesterol in blood (an hepatic estrogenic action). Thus, these short chain and nonpolar 11beta-analogues of estradiol have tissue specific antiestrogenic/estrogenic actions, characteristics of selective estrogen receptor modulators.

  DOI：

  10.1021/jm049352x

文献信息

• 11beta-short chain substituted estradiol analogs and their use in the treatment of menopausal symptoms and estrogen sensitive cancer
  申请人：YALE UNIVERSITY

  公开号：US20040142915A1

  公开（公告）日：2004-07-22

  The present invention relates to novel 11-&bgr; estradiol ester compounds and their use as locally active estrogens in the treatment of the symptomology of menopause and to treat estrogen sensitive cancers, including breast cancer.

  本发明涉及新型11-β雌二醇酯化合物及其作为局部活性雌激素在治疗更年期症状和治疗雌激素敏感性癌症，包括乳腺癌中的用途。