3β-(p-fluorobenzoyloxy)pregna-4,16-diene-6,20-dione

• 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: 3β-(p-fluorobenzoyloxy)pregna-4,16-diene-6,20-dione
• 英文别名: 3β-p-fluorobenzoyloxpregn-4,16-diene-6,20-dione；3beta-(p-Fluorobenzoyloxy)-4,16-pregnadiene-6,20-dione；[(3S,8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-6-oxo-1,2,3,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-yl] 4-fluorobenzoate
• 化学式: C₂₈H₃₁FO₄
• 分子量: 450.55
• InChiKey: JZGAYHASUNFQDT-BDVCAQFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 吡啶 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium hydroxide 、 氯化亚砜 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 3.08h， 生成 3β-(p-fluorobenzoyloxy)pregna-4,16-diene-6,20-dione
  参考文献：
  名称：

  New 5?-reductase inhibitors: In vitro and in vivo effects

  摘要：

  The enzyme 5 alpha-reductase is responsible for the conversion of testosterone (T) to its more potent androgen dihydrotestosterone (DHT). This steroid had been implicated in androgen-dependent diseases such as: benign prostatic hyperplasia. prostate cancer, acne and androgenic alopecia. The inhibition of 5 alpha-reductase enzyme offers a potentially useful treatment for these diseases.In this study, we report the synthesis and pharmacological evaluation of several new 3-substituted pregna-4, 16-diene-6, 20-dione derivatives. These compounds were prepared from the commercially available 16-dehydropregnenolone acetate. The biological activity of the new steroidal derivatives was determined in vivo as well as in vitro experiments.In vivo experiments, the anti-androgenic effect of the steroids was demonstrated by the decrease of the weight of the prostate gland of gonadectomized hamster treated with T plus finasteride or the new steroids. The IC50 value of these steroids was determined by measuring the conversion of radio labeled T to DHT.The results of this study carried out with 5 alpha-reductase enzyme from hamster and human prostate showed that four of the six steroidal derivatives (5, 7, 9, 10) exhibited much higher 5 alpha-reductase inhibitory activity, as indicated by the IC50 values than the presently used Proscar 3 (finasteride).The comparison of the weight of the hamster's prostate gland indicated that compound 5 had a comparable weight decrease as finasteride. The overall data of this study showed very clearly those compounds 5, 7, 9, 10 are good inhibitors for the 5 alpha-reductase enzyme. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.11.008

文献信息

• New 5?-reductase inhibitors: In vitro and in vivo effects
  作者：V PEREZORNELAS、M CABEZA、E BRATOEFF、I HEUZE、M SANCHEZ、E RAMIREZ、E NARANJORODRIGUEZ

  DOI：10.1016/j.steroids.2004.11.008

  日期：2005.3

  The enzyme 5 alpha-reductase is responsible for the conversion of testosterone (T) to its more potent androgen dihydrotestosterone (DHT). This steroid had been implicated in androgen-dependent diseases such as: benign prostatic hyperplasia. prostate cancer, acne and androgenic alopecia. The inhibition of 5 alpha-reductase enzyme offers a potentially useful treatment for these diseases.In this study, we report the synthesis and pharmacological evaluation of several new 3-substituted pregna-4, 16-diene-6, 20-dione derivatives. These compounds were prepared from the commercially available 16-dehydropregnenolone acetate. The biological activity of the new steroidal derivatives was determined in vivo as well as in vitro experiments.In vivo experiments, the anti-androgenic effect of the steroids was demonstrated by the decrease of the weight of the prostate gland of gonadectomized hamster treated with T plus finasteride or the new steroids. The IC50 value of these steroids was determined by measuring the conversion of radio labeled T to DHT.The results of this study carried out with 5 alpha-reductase enzyme from hamster and human prostate showed that four of the six steroidal derivatives (5, 7, 9, 10) exhibited much higher 5 alpha-reductase inhibitory activity, as indicated by the IC50 values than the presently used Proscar 3 (finasteride).The comparison of the weight of the hamster's prostate gland indicated that compound 5 had a comparable weight decrease as finasteride. The overall data of this study showed very clearly those compounds 5, 7, 9, 10 are good inhibitors for the 5 alpha-reductase enzyme. (c) 2005 Elsevier Inc. All rights reserved.
• Synthesis and cytotoxic effect on cancer cell lines and macrophages of novel progesterone derivatives having an ester or a carbamate function at C-3 and C-17
  作者：Alejandra Chávez-Riveros、Mariana Garrido、María Teresa Ramírez Apan、Armando Zambrano、Mario Díaz、Eugene Bratoeff

  DOI：10.1016/j.ejmech.2014.06.008

  日期：2014.7

  In this study we report the cytotoxic effect on human cancer cells of two series of novel progesterone derivatives; the first containing an aromatic ester (8a-e) or a carbamate functions both linked to C-3 (9a -e) on the pregn-4,16-diene-6,20-dione skeleton. In the second series, both functional groups (ester and carbamate) are bound to C-17 on the pregn-4,6-diene-3,20-dione scaffold (13a-e and 14a-e). The panel cancer cell lines used in this study were the following: PC-3 (human prostate cancer cell line), MCF-7 (human breast cancer cell line), HCT-15 (human colon cancer cell line) and J774 (noncancerous murine macrophages) for comparison.The results from this study showed that steroid 14a, having a carbamate function at C-17, was the most potent against PC-3 cell line (96.6%) while 8c and 8e showed much higher cytotoxic activity (100%) for MCF-7 cell line. Finally, compounds 8c and 14a displayed selective properties towards tumor cell lines than noncancerous murine macrophages. (C) 2014 Elsevier Masson SAS. All rights reserved.