3-benxyloxy-11β-butoxyestra-1,3,5(10)-trien-17-one | 849241-52-7

• 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: 3-benxyloxy-11β-butoxyestra-1,3,5(10)-trien-17-one
• 英文别名: (8S,9S,11S,13S,14S)-11-butoxy-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 849241-52-7
• 化学式: C₂₉H₃₆O₃
• 分子量: 432.603
• InChiKey: FSVNGYWVDZNDSE-GVQQRXEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benxyloxy-11β-butoxyestra-1,3,5(10)-trien-17-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以31 mg的产率得到3-benxyloxy-11β-butoxyestra-1,3,5(10)-trien-17β-ol
  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：

  3-benxyloxy-11β-butoxy-17,17-ethylenedioxyestra-1,3,5(10)-triene 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 3-benxyloxy-11β-butoxyestra-1,3,5(10)-trien-17-one
  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

• Nonpolar and Short Side Chain Groups at C-11β of Estradiol Result in Antiestrogens
  作者：Jing-xin Zhang、David C. Labaree、Richard B. Hochberg

  DOI：10.1021/jm049352x

  日期：2005.3.1

  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.