pregn-4-ene-3,20-dione 3-thiosemicarbazone | 2479-83-6

• 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: pregn-4-ene-3,20-dione 3-thiosemicarbazone
• 英文别名: [[(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]amino]thiourea
• CAS: 2479-83-6
• 化学式: C₂₂H₃₃N₃OS
• 分子量: 387.59
• InChiKey: UQSPAOWRWUOFLV-VPQCCYDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pregn-4-ene-3,20-dione 3-thiosemicarbazone 、 乙酸酐 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以77%的产率得到(3R)-N-(3'-acetyl-20-oxospiro[pregn-4-ene-3,2'-[1,3,4]thiadiazoline]-5'-yl)acetamide
  参考文献：
  名称：

  新型甾体硫代半脲和噻二唑啉的 合成，表征和体外细胞毒性活性†

  摘要：

  合成，表征和表征了一系列新的甾体单和双（硫代半氨基甲酮）（2a–e和3a–e）以及相应的单和双（1,3,4-噻二唑啉）（4a–e和5a–e）。评估其抗癌活性。详细的NMR分析的单和双（thiosemicarbazones）揭示了在C-3位置的moiety部分中存在两个构型不同的立体异构体（Z和E），其中C（3）N双键上的取代基位于主要异构体采用E构型。噻唑啉4a–e和5a–e中C-3和C-17的构型通过详细的NMR分析以及Dreiding分子模型的检查和3-噻二唑啉4a的X射线分析得出了C的结构和绝对构型，从而确定了C-3的结构和绝对构型。测试了合成的化合物对六种癌细胞系（HeLa，K562，MDA-MB-361，MDA-MB-453，LS174和A549），正常人细胞系MRC-5和从中分离的外周血单核细胞（PBMC）的作用。健康的捐助者。最好的活性表现在3-thiosemicarbazones

  DOI：

  10.1039/c6ra01516f
• 作为产物：
  描述：

  黄体酮 、 氨基硫脲 以 甲醇 为溶剂， 反应 8.0h， 以60%的产率得到pregn-4-ene-3,20-dione 3-thiosemicarbazone
  参考文献：
  名称：

  Hybrid anticancer agents: Isothiocyanate–progesterone conjugates as chemotherapeutic agents and insights into their cytotoxicities

  摘要：

  New hybrid molecules of isothiocyanate and progesterone and their metal complexes were synthesized exhibiting promising anti-proliferative and pro-apoptotic activity against breast and prostate cancer cells. These metal complex compounds exploited an existing cellular transport pathway for delivery of cytotoxic isothiocyanate moiety across cell membrane resulting in the inhibition of cell viability and inducing apoptosis. The highest apoptotic action was shown by the copper complex, which was mediated through the inhibition of Akt signaling similar to the one shown by isothiocyanate compounds. Our results underscore the possible role of metal redox cycling, and thus it is likely will open newer avenues for further optimization for the synthesis of novel active compounds through appropriate isothiocyanate pharmacophores. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.11.128

文献信息

• Hybrid anticancer agents: Isothiocyanate–progesterone conjugates as chemotherapeutic agents and insights into their cytotoxicities
  作者：Shreelekha Adsule、Sanjeev Banerjee、Fakhara Ahmed、Subhash Padhye、Fazlul H. Sarkar

  DOI：10.1016/j.bmcl.2009.11.128

  日期：2010.2

  New hybrid molecules of isothiocyanate and progesterone and their metal complexes were synthesized exhibiting promising anti-proliferative and pro-apoptotic activity against breast and prostate cancer cells. These metal complex compounds exploited an existing cellular transport pathway for delivery of cytotoxic isothiocyanate moiety across cell membrane resulting in the inhibition of cell viability and inducing apoptosis. The highest apoptotic action was shown by the copper complex, which was mediated through the inhibition of Akt signaling similar to the one shown by isothiocyanate compounds. Our results underscore the possible role of metal redox cycling, and thus it is likely will open newer avenues for further optimization for the synthesis of novel active compounds through appropriate isothiocyanate pharmacophores. Published by Elsevier Ltd.
• Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines
  作者：Marijana B. Živković、Ivana Z. Matić、Marko V. Rodić、Irena T. Novaković、Dušan M. Sladić、Natalija M. Krstić

  DOI：10.1039/c6ra01516f

  日期：——

  The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition

  合成，表征和表征了一系列新的甾体单和双（硫代半氨基甲酮）（2a–e和3a–e）以及相应的单和双（1,3,4-噻二唑啉）（4a–e和5a–e）。评估其抗癌活性。详细的NMR分析的单和双（thiosemicarbazones）揭示了在C-3位置的moiety部分中存在两个构型不同的立体异构体（Z和E），其中C（3）N双键上的取代基位于主要异构体采用E构型。噻唑啉4a–e和5a–e中C-3和C-17的构型通过详细的NMR分析以及Dreiding分子模型的检查和3-噻二唑啉4a的X射线分析得出了C的结构和绝对构型，从而确定了C-3的结构和绝对构型。测试了合成的化合物对六种癌细胞系（HeLa，K562，MDA-MB-361，MDA-MB-453，LS174和A549），正常人细胞系MRC-5和从中分离的外周血单核细胞（PBMC）的作用。健康的捐助者。最好的活性表现在3-thiosemicarbazones