3β-hydroxy-23t(?)-[2]pyridyl-21,24-dinor-chola-5,22-dien-20-one | 122339-04-2

• 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-hydroxy-23t(?)-[2]pyridyl-21,24-dinor-chola-5,22-dien-20-one
• 英文别名: 3β-hydroxy-23t-[2]pyridyl-21,24-dinor-chola-5,22-dien-20-one；3β-Hydroxy-23t-[2]pyridyl-21,24-dinor-chola-5,22-dien-20-on
• CAS: 122339-04-2
• 化学式: C₂₇H₃₅NO₂
• 分子量: 405.58
• InChiKey: LYRLKCOSYRYHQM-SVGKEPBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  50.19
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-23t(?)-[2]pyridyl-21,24-dinor-chola-5,22-dien-20-one 在 环己酮 、 aluminum isopropoxide 、 甲苯 作用下， 生成 23t(?)-[2]pyridyl-21,24-dinor-chola-4,22-diene-3,20-dione
  参考文献：
  名称：

  17-(pyridineacrylyl)-4-androsten-3-ones

  摘要：

  公开号：

  US02862923A1
• 作为产物：
  描述：

  吡啶-2-甲醛 、 孕烯醇酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以79%的产率得到3β-hydroxy-23t(?)-[2]pyridyl-21,24-dinor-chola-5,22-dien-20-one
  参考文献：
  名称：

  孕烯醇酮作为新型抗骨质疏松剂的杂环类似物的合成和生物学评估。

  摘要：

  孕烯醇酮的结构修饰已通过限制酰基在C-17位上引入杂环部分进行了描述。通过使用Friedlander和Claisen-Schmidt反应合成了孕烯醇酮的新型杂环类似物，并对合成的化合物的成骨活性进行了评估。在合成的衍生物中，四种化合物显示出显着提高的ALP活性。在所有四种活性化合物中，新型化合物3a在1pM浓度下均显示出显着的骨基质矿化和成骨标记基因BMP2，RUNX-2和OCN的mRNA表达。

  DOI：

  10.1016/j.bmcl.2017.02.004

文献信息

• Pregnenolone derivatives as potential anticancer agents
  作者：M. Iqbal Choudhary、M. Shahab Alam、Atta-ur-Rahman、Sammer Yousuf、Yang-Chang Wu、An-Shen Lin、F. Shaheen

  DOI：10.1016/j.steroids.2011.09.006

  日期：2011.12

  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.
• 17-pyridineacrylyl-5-androsten-3-ols and their esters
  申请人：SEARLE &

  公开号：US02753341A1

  公开（公告）日：1956-07-03