(25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate

• 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: (25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate
• 英文别名: [(3S,10R,13S,16S,17R)-16-acetyloxy-17-[(2S,6R)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• 化学式: C₃₁H₄₈O₆
• 分子量: 516.719
• InChiKey: INUVWOFKWFJJFJ-GYJPOGSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate 在 4-二甲氨基吡啶 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 (25R)-22-oxo-26-selenocyanocholest-5-en-3β,16β-diyl diacetate
  参考文献：
  名称：

  Probing the selective antitumor activity of 22-oxo-26-selenocyanocholestane derivatives

  摘要：

  Diverse steroidal compounds have shown antiproliferative activity on certain tumor cell lines; however, their complete role on cancer cells has not been extensively established since the research is quite recent. Hence, deeper study in this field is required. Due to the importance of selenium in animal and human health; herein, we report the synthesis, characterization, and biological evaluation of two novel 22-oxo-26-selenocyanocholestanic steroids on cervicouterine cancer cells and non-tumor cells. The title compounds were straightforward prepared from diosgenin and hecogenin in excellent overall yields. We determined their effect on cell proliferation on HeLa, CaSki, and ViBo cell cultures. Their cytotoxic effect on tumor cells, as well as on peripheral blood lymphocytes was also evaluated. The increase in the expression of active caspase-3 along with the fragmentation of DNA confirm that the new 22-oxo-26selenocyanocholestane frameworks potentiate apoptosis in tumor cells. The antiproliferative activity on tumor cells affects to some extent the proliferative potential of peripheral blood lymphocytes, so an immunosuppressive effect has also been established. The novel 22-oxo-26-selenocyanocholestane compounds show selective antitumor activity and therefore are promising lead candidates for further in vivo evaluation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.059
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 (25R)-26-hydroxy-22-oxocholest-5-en-3β,16β-diyl diacetate
  参考文献：
  名称：

  Fused Pyrroles in Cholestane and Norcholestane Side Chains: Acaricidal and Plant Growth-Promoting Effects

  摘要：

  在本文中，我们介绍了分别从色原甙元和薯蓣皂苷提取的胆甾烷和去甲胆甾烷侧链融合吡咯的合成和表征。我们采用传统和微波加热技术从伯胺中合成了甾体吡咯，其中微波法的产率最高。特别是，在实验室条件下，这些去甲胆甾烷吡咯类化合物作为杀螨剂对抗二斑蜘蛛螨（Tetranychus urticae Koch）；在温室条件下，这些吡咯类化合物作为植物生长促进剂促进哈瓦那辣椒（Capsicum chinense Jacq）的生长。

  DOI：

  10.3390/molecules27238466

文献信息

• Probing the selective antitumor activity of 22-oxo-26-selenocyanocholestane derivatives
  作者：María A. Fernández-Herrera、Jesús Sandoval-Ramírez、Luis Sánchez-Sánchez、Hugo López-Muñoz、María L. Escobar-Sánchez

  DOI：10.1016/j.ejmech.2013.12.059

  日期：2014.3

  Diverse steroidal compounds have shown antiproliferative activity on certain tumor cell lines; however, their complete role on cancer cells has not been extensively established since the research is quite recent. Hence, deeper study in this field is required. Due to the importance of selenium in animal and human health; herein, we report the synthesis, characterization, and biological evaluation of two novel 22-oxo-26-selenocyanocholestanic steroids on cervicouterine cancer cells and non-tumor cells. The title compounds were straightforward prepared from diosgenin and hecogenin in excellent overall yields. We determined their effect on cell proliferation on HeLa, CaSki, and ViBo cell cultures. Their cytotoxic effect on tumor cells, as well as on peripheral blood lymphocytes was also evaluated. The increase in the expression of active caspase-3 along with the fragmentation of DNA confirm that the new 22-oxo-26selenocyanocholestane frameworks potentiate apoptosis in tumor cells. The antiproliferative activity on tumor cells affects to some extent the proliferative potential of peripheral blood lymphocytes, so an immunosuppressive effect has also been established. The novel 22-oxo-26-selenocyanocholestane compounds show selective antitumor activity and therefore are promising lead candidates for further in vivo evaluation. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Fused Pyrroles in Cholestane and Norcholestane Side Chains: Acaricidal and Plant Growth-Promoting Effects
  作者：María G. De los Santos、Marcos Cua-Basulto、Anallely Huepalcalco、Wendy Delit、Jesús Sandoval-Ramírez、Adolfo López-Torres、Esaú Ruiz-Sánchez、María A. Fernández-Herrera

  DOI：10.3390/molecules27238466

  日期：——

  Herein, we describe the synthesis and characterization of fused pyrroles in cholestane and norcholestane side chains derived from kryptogenin and diosgenin, respectively. Both conventional and microwave heating techniques were used to synthesize the steroidal pyrroles from primary amines, with the microwave method producing the highest yields. In particular, the norcholestane pyrroles were tested as acaricides against the two-spotted spider mite (Tetranychus urticae Koch) under laboratory conditions and as plant growth promoters on habanero pepper (Capsicum chinense Jacq) under greenhouse conditions.

  在本文中，我们介绍了分别从色原甙元和薯蓣皂苷提取的胆甾烷和去甲胆甾烷侧链融合吡咯的合成和表征。我们采用传统和微波加热技术从伯胺中合成了甾体吡咯，其中微波法的产率最高。特别是，在实验室条件下，这些去甲胆甾烷吡咯类化合物作为杀螨剂对抗二斑蜘蛛螨（Tetranychus urticae Koch）；在温室条件下，这些吡咯类化合物作为植物生长促进剂促进哈瓦那辣椒（Capsicum chinense Jacq）的生长。