1-benzyl-3-(3-pyridyl)-2-thiourea | 60572-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-benzyl-3-(3-pyridyl)-2-thiourea
• 英文别名: 1-benzyl-3-pyridin-3-yl-thiourea；1-Benzyl-3-pyridin-3-ylthiourea
• CAS: 60572-51-2
• 化学式: C₁₃H₁₃N₃S
• mdl: MFCD06139686
• 分子量: 243.332
• InChiKey: ZIERMWDJPNPBBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氨基吡啶 、 异硫氰酸苯甲酯 以 苯 为溶剂， 以78%的产率得到1-benzyl-3-(3-pyridyl)-2-thiourea
  参考文献：
  名称：

  摘要：

  Purpose. To design new antithyroid agents with less side effects, the electrotopological-state (E-state) indexes of thiourylene moiety (S-N&S) was utilized as a guideline to develop five acyclic thiourylene-type compounds with reduced antioxidant property.Methods. These agents were synthesized and screened for antithyroid activity in rats using I-125-thiocyanate discharge technique. In addition, chemiluminescence studies on the activated polymorphonuclear leukocytes (PMNLs) were also conducted to reveal antioxidant properties of the tested compounds.Results. A linear relationship between the in vitro literature value of the formation constants of thiourylene-type compounds with iodine (K-c) and the S-N&S was observed and utilized in designing those agents. At least one of the compounds (abouthiouzine) was found to have a potential value as an antithyroid agent. The relative efficacy of abouthiouzine [1-n-butyl-3(isonicotinamido)-2-thiourea], after equimolar dose, was 102% and 51.5% of that of propylthiouracil with respect to the rate of I-125-discharge and I-125-uptake, respectively. In addition, Chemiluminescence studies on PMNLs revealed that abouthiouzine has slight oxidant property. Such properties may provide advantages in avoiding the iatrogenic hypothyroidism and antithyroid-induced immunological reactions.Conclusions. The E-state approach provides guidelines to economize efforts and cost of designing new antithyroid drugs.

  DOI：

  10.1023/a:1016049921842

文献信息

• ——
  作者：Rafiq R. A. Abou‐Shaaban、Hamad A. Al‐Khamees、Hisham S. Abou‐Auda、Anthony. P. Simonelli

  DOI：10.1023/a:1016049921842

  日期：——

  Purpose. To design new antithyroid agents with less side effects, the electrotopological-state (E-state) indexes of thiourylene moiety (S-N&S) was utilized as a guideline to develop five acyclic thiourylene-type compounds with reduced antioxidant property.Methods. These agents were synthesized and screened for antithyroid activity in rats using I-125-thiocyanate discharge technique. In addition, chemiluminescence studies on the activated polymorphonuclear leukocytes (PMNLs) were also conducted to reveal antioxidant properties of the tested compounds.Results. A linear relationship between the in vitro literature value of the formation constants of thiourylene-type compounds with iodine (K-c) and the S-N&S was observed and utilized in designing those agents. At least one of the compounds (abouthiouzine) was found to have a potential value as an antithyroid agent. The relative efficacy of abouthiouzine [1-n-butyl-3(isonicotinamido)-2-thiourea], after equimolar dose, was 102% and 51.5% of that of propylthiouracil with respect to the rate of I-125-discharge and I-125-uptake, respectively. In addition, Chemiluminescence studies on PMNLs revealed that abouthiouzine has slight oxidant property. Such properties may provide advantages in avoiding the iatrogenic hypothyroidism and antithyroid-induced immunological reactions.Conclusions. The E-state approach provides guidelines to economize efforts and cost of designing new antithyroid drugs.