N-[4-hydroxy-3-(3-methoxyphenyl)-2-thiazolidinylidene]-4-methylphenylsulfonamide | 247031-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[4-hydroxy-3-(3-methoxyphenyl)-2-thiazolidinylidene]-4-methylphenylsulfonamide
• 英文别名: N-[4-hydroxy-3-(3-methoxyphenyl)-1,3-thiazolidin-2-ylidene]-4-methylbenzenesulfonamide
• CAS: 247031-67-0
• 化学式: C₁₇H₁₈N₂O₄S₂
• 分子量: 378.473
• InChiKey: PZWNCIVJYBGSNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.2
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[4-hydroxy-3-(3-methoxyphenyl)-2-thiazolidinylidene]-4-methylphenylsulfonamide 在 盐酸 、 三溴化硼 、 碳酸氢钠 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 3-[2,3-dihydro-2-[[(4-methylphenyl)sulfonyl]imino]thiazol-3-yl]phenoxyacetic acid
  参考文献：
  名称：

  Synthesis, structural characterization and thromboxane A2 receptor antagonistic activity of 3-substituted 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives

  摘要：

  A series of new 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives substituted on the heterocyclic N by a phenoxyacetic moiety was prepared according to a Hantzsch's synthesis between N, N'-disubstituted thioureas and chloroacetaldehyde. The regiochemistry of the cyclocondensation reaction was established by high resolution NMR methods. Potential thromboxane A(2)/prostaglandin H-2 (TxA(2)/PGH(2)) receptor antagonism was evaluated using human platelet aggregation assays and radioligand binding studies. The results showed that the affinity for the TxA(2)/PGH(2) receptor was strongly dependent on the position of the oxyacetic acid side chain. On the basis of the X-ray crystal analysis of compound 9f, a molecular modelling was undertaken on compounds 3d, 3e, and 3f. Comparison with the 3D structure of sulotroban was discussed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80082-8
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.5h， 生成 N-[4-hydroxy-3-(3-methoxyphenyl)-2-thiazolidinylidene]-4-methylphenylsulfonamide
  参考文献：
  名称：

  Synthesis, structural characterization and thromboxane A2 receptor antagonistic activity of 3-substituted 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives

  摘要：

  A series of new 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives substituted on the heterocyclic N by a phenoxyacetic moiety was prepared according to a Hantzsch's synthesis between N, N'-disubstituted thioureas and chloroacetaldehyde. The regiochemistry of the cyclocondensation reaction was established by high resolution NMR methods. Potential thromboxane A(2)/prostaglandin H-2 (TxA(2)/PGH(2)) receptor antagonism was evaluated using human platelet aggregation assays and radioligand binding studies. The results showed that the affinity for the TxA(2)/PGH(2) receptor was strongly dependent on the position of the oxyacetic acid side chain. On the basis of the X-ray crystal analysis of compound 9f, a molecular modelling was undertaken on compounds 3d, 3e, and 3f. Comparison with the 3D structure of sulotroban was discussed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80082-8