1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-(3-nitrophenyl)prop-2-en-1-one | 1352081-24-3

• 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: 1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-(3-nitrophenyl)prop-2-en-1-one
• CAS: 1352081-24-3
• 化学式: C₂₈H₃₅NO₄
• 分子量: 449.59
• InChiKey: LGPPNAZRDMHWSN-XMLICAENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  80.44
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-(3-nitrophenyl)prop-2-en-1-one 在 吡啶 、 盐酸羟胺 作用下， 反应 22.0h， 生成 1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-(3-nitrophenyl)prop-2-en-1-one oxime
  参考文献：
  名称：

  Pregnenolone derivatives as potential anticancer agents

  摘要：

  Pregnenolone (1) was used as a template to develop new anticancer compounds. Ring-D modification of 1 resulted in the synthesis of benzylidenes 2-17, pyrazolines 18-76, pyrazoles 85-91, hydrazones 77-84, and oximes 92-107 derivatives. The structure of compound 107 was also deduced through single crystal X-ray diffraction studies. The inclusion of furanyl and pyridyl rings to pregnenolone skeleton increases the cytotoxicity of all compounds significantly. Among benzylidene derivatives, only heterocyclic enone 8 (IC50 = 0.74 mu M/mL against HepG2), and 17 (IC50 = 4.49 mu M/mL against HepG2, IC50 = 5.01 mu M/mL against MDA-MB-230 cancer cell line) exhibited a significant activity. The cytotoxicity data of pyrazoline derivatives 18-76 revealed that only furanyl bearing pyrazolines 40,42-44,48, and 49 exhibited significant activities. While all (O-carboxymethyl) oximes, hydazones, and pyrazoles derivatives of pregnenolone did not show any significant activity against both the cell lines. Thus the furanyl bearing enone 8 (IC50 = 0.74 mu M/mL against HepG2), and its pyrazoline derivative 48 (IC50 = 0.91 mu M/mL against MDA-MB-230 cancer cell lines) were identified as the most active compounds in all derivatives of pregnenolone. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.09.006
• 作为产物：
  描述：

  孕烯醇酮 、 间硝基苯甲醛 在 aluminum oxide 、 potassium fluoride 作用下， 以 乙醇 为溶剂， 生成 1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-3-(3-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  新的甾体吡啶类化合物作为潜在的抗前列腺癌药物的合成及生物学评价

  摘要：

  通过基于基础的三组分反应合成了一系列新的甾族吡啶，并初步评估了它们对不同类型癌细胞系的抗增殖活性。SARs研究表明，与吡啶环相比，连接吡啶环4位的杂环具有更好的活性。在这些化合物中，最有效的化合物对所有测试的癌细胞均表现出良好的生长抑制作用，尤其是对于具有IC 50的PC-3细胞值为1.55μM。进一步的机理研究表明，最有效的化合物可能以浓度依赖的方式抑制PC-3细胞的集落形成，迁移和逃逸，并可能通过线粒体相关的凋亡途径诱导PC-3细胞凋亡。Caspase-3 / -9和PARP被激活，最终导致PC-3细胞凋亡。对于雄激素敏感（AR +）前列腺癌细胞系LNCaP，使用IC 50时，最有效的化合物的效力低于阿比特龙值分别为8.48和3.29μM。最有效的化合物可以用作开发具有改进的抗癌效力和选择性的新型甾族杂环的起点。合成的类固醇吡啶含有功能性-OEt和CN基团，可用于进一步修饰以构建类固醇文库。

  DOI：

  10.1016/j.ejmech.2017.12.094