5-pyridin-2-ylmethylene-2-thioxo-imidazolidin-4-one | 32080-65-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-pyridin-2-ylmethylene-2-thioxo-imidazolidin-4-one
• 英文别名: 5-[(Pyridin-2-yl)methylidene]-2-sulfanylideneimidazolidin-4-one；5-(pyridin-2-ylmethylidene)-2-sulfanylideneimidazolidin-4-one
• CAS: 32080-65-2
• 化学式: C₉H₇N₃OS
• mdl: MFCD00297111
• 分子量: 205.24
• InChiKey: DRMFCOHNVXPTHL-UHFFFAOYSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-pyridin-2-ylmethylene-2-thioxo-imidazolidin-4-one 在 甲醇 、 氨 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 36.0h， 生成 5-[1-Pyridin-2-yl-meth-(Z)-ylidene]-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-imidazolidine-2,4-dione
  参考文献：
  名称：

  A CONVENIENT SYNTHESIS OF GLYCOSYLATED HYDANTOINS AS POTENTIAL ANTIVIRAL AGENTS

  摘要：

  Reaction of 5-arylidene-2-thiohydantoins 3a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. Deacetylation with ammonia in methanol caused a change of the S-glycosyl residue and gave the N-3 glycosylated analogues 7a-h. S-Glycosylation also occured when N-3 substituted hydantoins 9a-h were reacted.

  DOI：

  10.1080/10426509708043491
• 作为产物：
  描述：

  吡啶-2-甲醛 、 2-硫代乙内酰脲 在 sodium acetate 、 溶剂黄146 作用下， 反应 2.0h， 以82%的产率得到5-pyridin-2-ylmethylene-2-thioxo-imidazolidin-4-one
  参考文献：
  名称：

  A CONVENIENT SYNTHESIS OF GLYCOSYLATED HYDANTOINS AS POTENTIAL ANTIVIRAL AGENTS

  摘要：

  Reaction of 5-arylidene-2-thiohydantoins 3a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. Deacetylation with ammonia in methanol caused a change of the S-glycosyl residue and gave the N-3 glycosylated analogues 7a-h. S-Glycosylation also occured when N-3 substituted hydantoins 9a-h were reacted.

  DOI：

  10.1080/10426509708043491

文献信息

• Étude de dérivés 5-arylidène-2-thiohydantoïnes à potentialité immunomodulatrice et anticancéreuse
  作者：V Chazeau、M Cussac、A Boucherle

  DOI：10.1016/0223-5234(92)90140-v

  日期：1992.9

  Various 5-arylidene-2-thiohydantoins, N3-substituted and/or S-substituted or not, were synthesized by aldolisation-crotonisation reaction from aromatic aldehydes or cyclic ketones and 2-thiohydantoins. These products, largely original, prepared as potentially active on chronic inflammatory diseases involving cellular-mediated immunity, display immunosuppressive activity which, however, remains clearly lower than ciclosporine's one. Searched in a few cases, anticancer activity is not obviously detected for any of tested products.