(3Ξ,5'Ξ)-dispiro[cholest-4-ene-3,3'-[1,2,4]trithiolane-5',3''-cholest-4''-ene] | 122386-34-9

• 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: (3Ξ,5'Ξ)-dispiro[cholest-4-ene-3,3'-[1,2,4]trithiolane-5',3''-cholest-4''-ene]
• 英文别名: (3Ξ,5'Ξ)-Dispiro[cholest-4-en-3,3'-[1,2,4]trithiolan-5',3''-cholest-4''-en]
• CAS: 122386-34-9
• 化学式: C₅₄H₈₈S₃
• 分子量: 833.491
• InChiKey: JTMPXKFLJAKWPK-UOYBTVPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.59
• 重原子数：
  57.0
• 可旋转键数：
  10.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-胆甾烯-3-酮 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以79%的产率得到(3Ξ,5'Ξ)-dispiro[cholest-4-ene-3,3'-[1,2,4]trithiolane-5',3''-cholest-4''-ene]
  参考文献：
  名称：

  一些 α,β-不饱和甾体酮的硫化

  摘要：

  选定的 α,β-不饱和甾体酮与劳森试剂 (LR) 在 CH2Cl2 和甲苯中在标准反应条件下的反应以及与五硫化二磷与六甲基二硅氧烷 (P4S10/HMDO) 的组合在 1,2-二氯苯 (ODCB) 下的反应研究了微波辐射，为此选择了几种胆甾烷、雄甾烷和孕烷羰基衍生物。根据试剂和溶剂，19 种新的含硫化合物，包括二硫酮 4c 和 4d、α,β-不饱和 3-硫酮 3a-e、二聚体硫化物 2a-e、1,2,4-三硫杂环戊烷 5a-e 和合成了三硫代膦酸酯 6b-e。所有新制备的化合物均通过 IR、1H-和 13C-NMR 光谱和元素分析进行​​表征。

  DOI：

  10.3390/molecules15053462

文献信息

• Bourdon, Bulletin de la Societe Chimique de France, 1958, p. 722,724
  作者：Bourdon

  DOI：——

  日期：——
• Steroid dimers—In vitro cytotoxic and antimicrobial activities
  作者：Natalija M. Krstić、Ivana Z. Matić、Zorica D. Juranić、Irena T. Novaković、Dušan M. Sladić

  DOI：10.1016/j.jsbmb.2014.06.005

  日期：2014.9

  The in vitro cytotoxic activity of previously synthesized steroid dimers with different spacer group (sulfide, trithiolane ring or phosphorotrithioate) and the substituent at C-17 position was tested for their possible effects against following human tumor cell lines: cervical adenocarcinoma (HeLa), chronic myelogenous leukemia (K562) and two human breast cancer cell lines (MDA-MB-361 and MDA-MB-453). These compounds, applied at micromolar concentrations, exhibited cytotoxic activity of different intensity (compared with cisplatin as a control), modality and selectivity in these malignant cell lines. The best activity against all four cell cancer lines was exhibited by dimer-sulfides. All screened compounds exerted concentration-dependent cytotoxic activity against leukemia K562 cells. The compounds which exerted the most pronounced cytotoxic action exhibited notably higher cytotoxic activities against K562, HeLa and MDA-MB-453 cells in comparison to resting and PHA-stimulated PBMC, pointing to a significant selectivity in their antitumor actions. Examination of the mechanisms of cytotoxicity on leukemia K562 cells revealed pro-apoptotic action of each of the investigated compounds applied at concentrations 2IC50. The most prominent pro-apoptotic action was exhibited by dimer-sulfide of cholest-4-en-3-one. Furthermore, almost all of the tested compounds at IC50 concentrations induced G1 phase cell cycle arrest in K562 cells. Antimicrobial activity against Gram-positive, Gram-negative bacteria and fungal cells, and toxicity to brine shrimp Artemia salina, were evaluated. There was no antibacterial activity. The best antifungal activity was exhibited against Saccharomyces cerevisiae by dimers linked with trithiolane ring, indicating a selective activity of investigated compounds.