20-benzyl-20α-hydroxy-4-pregnen-3-one | 395652-72-9

• 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: 20-benzyl-20α-hydroxy-4-pregnen-3-one
• 英文别名: (8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-1-phenylpropan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 395652-72-9
• 化学式: C₂₈H₃₈O₂
• 分子量: 406.609
• InChiKey: JSRLAEPRLUOPMM-RMIXPHLWSA-N

物化性质

• 沸点：
  546.9±19.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  20-benzyl-20α-hydroxy-4-pregnen-3-one 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 以53%的产率得到20-benzyl-4β,5β-epoxy-20α-hydroxy-pregnan-3-one
  参考文献：
  名称：

  Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group

  摘要：

  Two series of compounds, benzyl alkylated at position 17 alpha and 20 of androstane and pregnane, respectively, were synthesised and tested for steroid sulphatase inhibition. We compared the ability of the compounds to inhibit steroid sulphatase obtained from two different sources (homogenates of transfected HEK-293 cells and Jeg-3 cells) and with two types of substrate (DHEAS or E1S). The inhibitory activity of 17 alpha -benzyl-5 alpha -androstane-3 beta ,17 beta -diol (7), 17 alpha -benzyl-5-androstene-3 beta ,17 beta -diol (9), 17 alpha -benzyl-4,17 beta -dihydroxy-4-androsten-3-one (15) and 20-benzyl-5-pregnene-3 beta ,20 alpha -diol (16) has proven to be superior to that of danazol, the first steroid sulphatase inhibitor to be reported, but still lower than that of the potent inhibitor estrone-3-O-sulphamate. The inhibitory activity of compound 7 was as potent as that of its previously reported estrane analogue, 17 alpha -benzyl estradiol. Benzyl alkylated compounds with no OH group on the A-ring (with a 4-OCH3, 4-Cl, or 4-H and their precursor epoxides), as well as a series of basic steroids without a benzyl group (ADT, epi-ADT, 3 alpha -diol, 3 beta -diol, DHEA, Delta (5)-diol, DHT, T, Preg and Prog), did not show steroid sulphatase inhibition. We have thus demonstrated that the steroid sulphatase inhibitory effect of a benzyl group, previously observed for an estrane nucleus, can be extended to certain androstane and pregnane nuclei bearing a 3 beta -OH or a 4-OH group. Inhibitors 7, 9, 15 and 16 did not induce any proliferative effect on androgen-sensitive Shionogi cells. However, when tested on oestrogen-sensitive ZR-75-1 cells, a proliferative effect was observed for 7 and 9, but not for 15 and 16. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01262-4
• 作为产物：
  描述：

  孕烯醇酮 在 cerium(III) chloride 环己酮 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.5h， 生成 20-benzyl-20α-hydroxy-4-pregnen-3-one
  参考文献：
  名称：

  Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group

  摘要：

  Two series of compounds, benzyl alkylated at position 17 alpha and 20 of androstane and pregnane, respectively, were synthesised and tested for steroid sulphatase inhibition. We compared the ability of the compounds to inhibit steroid sulphatase obtained from two different sources (homogenates of transfected HEK-293 cells and Jeg-3 cells) and with two types of substrate (DHEAS or E1S). The inhibitory activity of 17 alpha -benzyl-5 alpha -androstane-3 beta ,17 beta -diol (7), 17 alpha -benzyl-5-androstene-3 beta ,17 beta -diol (9), 17 alpha -benzyl-4,17 beta -dihydroxy-4-androsten-3-one (15) and 20-benzyl-5-pregnene-3 beta ,20 alpha -diol (16) has proven to be superior to that of danazol, the first steroid sulphatase inhibitor to be reported, but still lower than that of the potent inhibitor estrone-3-O-sulphamate. The inhibitory activity of compound 7 was as potent as that of its previously reported estrane analogue, 17 alpha -benzyl estradiol. Benzyl alkylated compounds with no OH group on the A-ring (with a 4-OCH3, 4-Cl, or 4-H and their precursor epoxides), as well as a series of basic steroids without a benzyl group (ADT, epi-ADT, 3 alpha -diol, 3 beta -diol, DHEA, Delta (5)-diol, DHT, T, Preg and Prog), did not show steroid sulphatase inhibition. We have thus demonstrated that the steroid sulphatase inhibitory effect of a benzyl group, previously observed for an estrane nucleus, can be extended to certain androstane and pregnane nuclei bearing a 3 beta -OH or a 4-OH group. Inhibitors 7, 9, 15 and 16 did not induce any proliferative effect on androgen-sensitive Shionogi cells. However, when tested on oestrogen-sensitive ZR-75-1 cells, a proliferative effect was observed for 7 and 9, but not for 15 and 16. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01262-4

文献信息

• Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group
  作者：Liviu C Ciobanu、Roch P Boivin、Van Luu-The、Donald Poirier

  DOI：10.1016/s0223-5234(01)01262-4

  日期：2001.8

  Two series of compounds, benzyl alkylated at position 17 alpha and 20 of androstane and pregnane, respectively, were synthesised and tested for steroid sulphatase inhibition. We compared the ability of the compounds to inhibit steroid sulphatase obtained from two different sources (homogenates of transfected HEK-293 cells and Jeg-3 cells) and with two types of substrate (DHEAS or E1S). The inhibitory activity of 17 alpha -benzyl-5 alpha -androstane-3 beta ,17 beta -diol (7), 17 alpha -benzyl-5-androstene-3 beta ,17 beta -diol (9), 17 alpha -benzyl-4,17 beta -dihydroxy-4-androsten-3-one (15) and 20-benzyl-5-pregnene-3 beta ,20 alpha -diol (16) has proven to be superior to that of danazol, the first steroid sulphatase inhibitor to be reported, but still lower than that of the potent inhibitor estrone-3-O-sulphamate. The inhibitory activity of compound 7 was as potent as that of its previously reported estrane analogue, 17 alpha -benzyl estradiol. Benzyl alkylated compounds with no OH group on the A-ring (with a 4-OCH3, 4-Cl, or 4-H and their precursor epoxides), as well as a series of basic steroids without a benzyl group (ADT, epi-ADT, 3 alpha -diol, 3 beta -diol, DHEA, Delta (5)-diol, DHT, T, Preg and Prog), did not show steroid sulphatase inhibition. We have thus demonstrated that the steroid sulphatase inhibitory effect of a benzyl group, previously observed for an estrane nucleus, can be extended to certain androstane and pregnane nuclei bearing a 3 beta -OH or a 4-OH group. Inhibitors 7, 9, 15 and 16 did not induce any proliferative effect on androgen-sensitive Shionogi cells. However, when tested on oestrogen-sensitive ZR-75-1 cells, a proliferative effect was observed for 7 and 9, but not for 15 and 16. (C) 2001 Editions scientifiques et medicales Elsevier SAS.