3-allyl-5-isopropyl-2-thiohydantoin | 114425-91-1

• 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: 3-allyl-5-isopropyl-2-thiohydantoin
• 英文别名: 5-(1-Methylethyl)-3-(2-propenyl)-2-thioxo-4-imidazolidinone；5-propan-2-yl-3-prop-2-enyl-2-sulfanylideneimidazolidin-4-one
• CAS: 114425-91-1
• 化学式: C₉H₁₄N₂OS
• mdl: MFCD01720980
• 分子量: 198.289
• InChiKey: UAXNBTRDSZOPPX-UHFFFAOYSA-N

物化性质

• 沸点：
  256.9±33.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-缬氨酸 、 天然芥菜籽油 在 disodium hydrogen phosphate - citric acid 作用下， 反应 48.0h， 生成 3-allyl-5-isopropyl-2-thiohydantoin
  参考文献：
  名称：

  Antimutagenic Properties of 3,5-Disubstituted 2-Thiohydantoins

  摘要：

  3,5-Disubstituted 2-thiohydantoins, which were prepared:by the reaction of allyl isothiocyanate (AITC) or 4-(methylthio)-3-butenyl isothiocyanate (MTBI) with various amino acids, were assayed for their inhibitory effects on the mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) on Salmonella typhimurium TA 98. When the 3,5-disubstituted 2-thiohydantoins (125-500 mu g/mL) were simultaneously preincubated with the bacterial strain, IQ (0.5 mu g/mL), and rat microsomal fraction (S9 mix) for 20 min, a dose-dependent inhibition of IQ mutagenicity was observed in the tested compounds except one prepared from MTBI and L-methionine. This inhibition ranged from 23% to 86%. The inhibitory effect either disappeared or was largely reduced to 5-19%, when the 3,5-disubstituted 2-thiohydantoins were added after metabolic activation of IQ with S9 mix. These results suggest that the 3,5-disubstituted 2-thiohydantoins probably acted as an inhibitor of the S9 mix-mediated metabolic activation of the mutagen.

  DOI：

  10.1021/jf980430x

文献信息

• Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives
  作者：Sushil Jha、Jon D. Silversides、Ross W. Boyle、Stephen J. Archibald

  DOI：10.1039/b924683e

  日期：——

  Hydantoins have been known as medicinally active compounds since the 1940s and thiohydantoin derivatives are currently undergoing clinical trials as potent androgen receptor antagonist drugs. Control of solid state properties including the formation of drug polymorphs is important to the pharmaceutical industry, and frequently results from different H-bonded motifs. N–H thiohydantoins show formation of H-bonded arrays in the solid state. Two novel and five known thiohydantoin derivatives were synthesised via reaction of alkyl isothiocyanates with amino acid methyl esters. X-Ray crystallographic data were obtained for all seven compounds showing that four of the structures contain hydrogen bonded dimeric units linked via N–H⋯S interactions and three of the structures have N–H⋯O linked H-bonded chains.

  自20世纪40年代以来，海因妥因（hydantoins）一直被认为具有药物活性，而硫代海因妥因衍生物目前正处于临床试验阶段，作为强效的雄激素受体拮抗剂药物。控制固态性质，包括药物多晶型的形成，对制药行业至关重要，并且通常源于不同的氢键模式。N-H硫代海因妥因在固态中显示出氢键阵列的形成。通过异硫氰酸烷基酯与氨基酸甲酯的反应合成了两种新型及五种已知的硫代海因妥因衍生物。对所有七种化合物获得了X射线晶体学数据，显示其中四种结构含有通过N-H⋯S相互作用链接的氢键二聚体单元，而另外三种结构则具有通过N-H⋯O链接的氢键链。
• Antimutagenic Properties of 3,5-Disubstituted 2-Thiohydantoins
  作者：Asaka Takahashi、Hiroki Matsuoka、Yoshio Ozawa、Yasushi Uda

  DOI：10.1021/jf980430x

  日期：1998.12.1

  3,5-Disubstituted 2-thiohydantoins, which were prepared:by the reaction of allyl isothiocyanate (AITC) or 4-(methylthio)-3-butenyl isothiocyanate (MTBI) with various amino acids, were assayed for their inhibitory effects on the mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) on Salmonella typhimurium TA 98. When the 3,5-disubstituted 2-thiohydantoins (125-500 mu g/mL) were simultaneously preincubated with the bacterial strain, IQ (0.5 mu g/mL), and rat microsomal fraction (S9 mix) for 20 min, a dose-dependent inhibition of IQ mutagenicity was observed in the tested compounds except one prepared from MTBI and L-methionine. This inhibition ranged from 23% to 86%. The inhibitory effect either disappeared or was largely reduced to 5-19%, when the 3,5-disubstituted 2-thiohydantoins were added after metabolic activation of IQ with S9 mix. These results suggest that the 3,5-disubstituted 2-thiohydantoins probably acted as an inhibitor of the S9 mix-mediated metabolic activation of the mutagen.