3β-hydroxy-5α-androstan-16-ylidene-[(sulfanyl)methyl-(2'-oxo-2'-phenylimino-N-(p-methylphenyl)ethanhydrazonothioate)]-17one | 1241792-28-8

• 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-5α-androstan-16-ylidene-[(sulfanyl)methyl-(2'-oxo-2'-phenylimino-N-(p-methylphenyl)ethanhydrazonothioate)]-17one
• CAS: 1241792-28-8
• 化学式: C₃₅H₄₃N₃O₃S₂
• 分子量: 617.877
• InChiKey: LVCDRTNZUBSZPY-VMYYXNJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  43.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  90.79
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  二硫化碳 、 表雄酮 、 2-anilino-N-(4-methylphenyl)-2-oxoethanehydrazonoyl chloride 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 3.0h， 以84%的产率得到3β-hydroxy-5α-androstan-16-ylidene-[(sulfanyl)methyl-(2'-oxo-2'-phenylimino-N-(p-methylphenyl)ethanhydrazonothioate)]-17one
  参考文献：
  名称：

  Facile Synthesis and in Vitro Cytotoxic Evaluation of Novel Thiadiazole, Pyrazole, and Dithiole-Androstane Derivatives

  摘要：

  In the aim of identifying new steroidal cytotoxic agents with potential antiproliferative activity against hepatoma cell lines (Hep-G2), we synthesized modified steroids containing the thiadiazole, pyrazole, or dithiole moiety. Epiandrosterone 1 reacted with carbon disulfide and sodium hydride to furnish -oxoketene dithio-disodium salt 2. Treatment of 2 with the hydrazonoyl halides 5a-d produced the thiadiazole anellated androstanone 7a-d, respectively. The reaction of 1 with hydrazine hydrate produced the hydrazide adduct 8, which cyclized upon reflux in acetic acid to form the condensed pyrazoloandrostanone derivative 9. Interaction of 8 with carbon disulfide and sodium hydride formed the disodium salt 10, which reacted with ethylchloroacetate to furnish the final adduct, dithioloandrostane derivative, 13. Compounds 7a, 7d, 9, and 13 were examined for their cytotoxicity against a panel of hepatoma cell lines (Hep-G2) using MTT assay. The results provide that, at incubation time 72 h, in DMSO, compound 7d (50 mol/mL) showed the most significant cytotoxic effect at P 0.05. The higher dose (100 mol/mL) of compound 7d, at 48 h incubation, reversed the effect causing resistance and the growth rate return to the control level. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903008914