17α-p-chlorobenzoyloxy-4,6-pregnadiene-3,20-dione | 1190878-47-7

• 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: 17α-p-chlorobenzoyloxy-4,6-pregnadiene-3,20-dione
• 英文别名: 17α-p-chlorobenzoiloxypregn-4,6-dien-3,20-dione；[(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] 4-chlorobenzoate
• CAS: 1190878-47-7
• 化学式: C₂₈H₃₁ClO₄
• 分子量: 467.005
• InChiKey: OMSJHHKCUFMFCN-BDPSOKNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 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：
  4

反应信息

• 作为产物：
  描述：

  醋羟孕酮 在 四氯苯醌 、 对甲苯磺酸 、 三氟乙酸酐 、 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 溶剂黄146 、 甲苯 为溶剂， 反应 9.0h， 生成 17α-p-chlorobenzoyloxy-4,6-pregnadiene-3,20-dione
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.06.008

文献信息

• Novel C-6 substituted and unsubstituted pregnane derivatives as 5α-reductase inhibitors and their effect on hamster flank organs diameter size
  作者：Marisa Cabeza、Armando Zambrano、Ivonne Heuze、Erick Carrizales、Anay Palacios、Tania Segura、Norma Valencia、Eugene Bratoeff

  DOI：10.1016/j.steroids.2009.04.009

  日期：2009.10

  C-6 all having an ester side chain at C-17 (benzoate ester bearing a Cl, F and a Br atom at C-4 position of the phenyl ring) on the 5alpha-reductase enzyme activity present in human prostate. In addition, it was also of interest to investigate the pharmacological effect on hamster flank organs diameter size. In order to study the structure-activity relationships of steroids 12a-12d, 14a-14d and 15

  本研究旨在确定在 C-6 (12a-12d) 处具有氯取代基、在 C-6 和 14a-14d 处具有溴取代基的 15、C-6 处没有任何卤素原子的几种孕酮衍生物的抑制作用所有在人前列腺中存在的 5α-还原酶活性的 C-17（苯甲酸酯在苯环的 C-4 位置带有一个 Cl、F 和一个 Br 原子）具有酯侧链。此外，研究对仓鼠胁腹器官直径大小的药理作用也很有趣。为了研究类固醇 12a-12d、14a-14d 和 15 的构效关系，我们确定了这些类固醇抑制人前列腺 5α-还原酶 (IC(50)) 50% 活性的浓度，以及由于这些化合物对仓鼠胁腹器官直径大小的体内​​作用。我们还使用标记的米勃龙 (MIB) 监测与雄激素受体的结合，确定了这些类固醇与大鼠前列腺细胞质中存在的雄激素受体结合的能力。该研究的结果表明，化合物 12a-12d（在 C-6 处具有氯取代基）、14a-14d（在 C-6 处缺少卤素原子）、13
• 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.