17β-methyl-16β-phenyl-17α-phenylacetoxy-D-homoandrost-4,6-diene-3,17a-dione | 918331-44-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 17β-methyl-16β-phenyl-17α-phenylacetoxy-D-homoandrost-4,6-diene-3,17a-dione
• 英文别名: [(2R,3R,4aS,4bR,10aR,10bS,12aS)-2,10a,12a-trimethyl-1,8-dioxo-3-phenyl-4,4a,4b,9,10,10b,11,12-octahydro-3H-chrysen-2-yl] 2-phenylacetate
• CAS: 918331-44-9
• 化学式: C₃₅H₃₈O₄
• 分子量: 522.684
• InChiKey: XMZXCWSHODLWRR-FQZQGJCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phenylacetic trifluoroacetic anhydride 、 17α-hydroxy-17β-methyl-16β-phenyl-D-homopregna-4,6-diene-3,17a-dione 在 对甲苯磺酸 作用下， 反应 2.0h， 以0.12 g的产率得到17β-methyl-16β-phenyl-17α-phenylacetoxy-D-homoandrost-4,6-diene-3,17a-dione
  参考文献：
  名称：

  New-D-homoandrost-4,6-diene derivatives as potent progesterone receptor antagonist

  摘要：

  The aim of this study was to synthesize three different D-homoandrostadiene derivatives (2-4) and study their biological activity. We carried out in vivo and in vitro experiments using female cycling mice, which were synchronized for estrus with luteinizing hormone-releasing hormone (LHRH) and injected with the steroidal compounds. It was also determined the binding of these compounds to the progesterone receptors (PR). Since these steroids have a new D-homoandrostandienone skeleton in their molecular structure, it was of interest also to study their binding to the androgen receptors (AR).After LHRH treatment, the mice of the control group showed the presence of 14 +/- 4 corpus lutea in the ovary whereas the animals treated with steroids 2-4, with RBAs of 100%, exhibited 11 +/- 7, 12 +/- 2, and 10 +/- 4 respectively. As a result of this study, it is evident that these steroids did not inhibit the ovulation in these animals.The uterus of the control group, showed the typical progestational activity with an enlarged endometrial thickness with a secretory activity. However, the endometrium of the mice treated with steroids 2-4 did not show an enlargement of the endometrium and no secretory activity could be detected. This fact indicates that compounds 2-4 had antagonistic activity in this tissue.The overall data show that steroids 2-4 are antagonists of the PR. However, they do not bind to the AR. These results also demonstrate that 2-4 have an anti progestational activity in vivo, but do not decrease the number of corpus lutea in the ovary of mice treated with LHRH. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.11.001

文献信息

• New-D-homoandrost-4,6-diene derivatives as potent progesterone receptor antagonist
  作者：Marisa Cabeza、Mario García-Lorenzana、Montserrat Garcés、Ivonne Heuze、Nayeli Teran、Eugene Bratoeff

  DOI：10.1016/j.steroids.2009.11.001

  日期：2010.1

  The aim of this study was to synthesize three different D-homoandrostadiene derivatives (2-4) and study their biological activity. We carried out in vivo and in vitro experiments using female cycling mice, which were synchronized for estrus with luteinizing hormone-releasing hormone (LHRH) and injected with the steroidal compounds. It was also determined the binding of these compounds to the progesterone receptors (PR). Since these steroids have a new D-homoandrostandienone skeleton in their molecular structure, it was of interest also to study their binding to the androgen receptors (AR).After LHRH treatment, the mice of the control group showed the presence of 14 +/- 4 corpus lutea in the ovary whereas the animals treated with steroids 2-4, with RBAs of 100%, exhibited 11 +/- 7, 12 +/- 2, and 10 +/- 4 respectively. As a result of this study, it is evident that these steroids did not inhibit the ovulation in these animals.The uterus of the control group, showed the typical progestational activity with an enlarged endometrial thickness with a secretory activity. However, the endometrium of the mice treated with steroids 2-4 did not show an enlargement of the endometrium and no secretory activity could be detected. This fact indicates that compounds 2-4 had antagonistic activity in this tissue.The overall data show that steroids 2-4 are antagonists of the PR. However, they do not bind to the AR. These results also demonstrate that 2-4 have an anti progestational activity in vivo, but do not decrease the number of corpus lutea in the ovary of mice treated with LHRH. (C) 2009 Elsevier Inc. All rights reserved.