2-[2,3-dihydro-2-[(phenylsulfonyl)imino]thiazol-3-yl]phenoxyacetic acid ethyl ester | 247031-76-1

• 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: 2-[2,3-dihydro-2-[(phenylsulfonyl)imino]thiazol-3-yl]phenoxyacetic acid ethyl ester
• 英文别名: ethyl 2-[2-[2-(benzenesulfonylimino)-1,3-thiazol-3-yl]phenoxy]acetate
• CAS: 247031-76-1
• 化学式: C₁₉H₁₈N₂O₅S₂
• 分子量: 418.494
• InChiKey: UPMIQWSKNMRMGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  86.96
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[2,3-dihydro-2-[(phenylsulfonyl)imino]thiazol-3-yl]phenoxyacetic acid ethyl ester 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.5h， 以64%的产率得到2-[2,3-dihydro-2-[(phenylsulfonyl)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：

  N-[4-hydroxy-3-(2-methoxyphenyl)-2-thiazolidinylidene]phenylsulfonamide 在 盐酸 、 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2-[2,3-dihydro-2-[(phenylsulfonyl)imino]thiazol-3-yl]phenoxyacetic acid ethyl ester
  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