3-((((4-chlorophenyl)sulfonyl)amino)methyl)phenoxy acetic acid | 138914-17-7

• 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: 3-((((4-chlorophenyl)sulfonyl)amino)methyl)phenoxy acetic acid
• 英文别名: (3-{[(4-Chlorobenzene-1-sulfonyl)amino]methyl}phenoxy)acetic acid；2-[3-[[(4-chlorophenyl)sulfonylamino]methyl]phenoxy]acetic acid
• CAS: 138914-17-7
• 化学式: C₁₅H₁₄ClNO₅S
• 分子量: 355.799
• InChiKey: YBUMMJYHBLTFGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氯苯磺酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 potassium carbonate 作用下， 生成 3-((((4-chlorophenyl)sulfonyl)amino)methyl)phenoxy acetic acid
  参考文献：
  名称：

  Thromboxane A2 receptor antagonists. Synthesis and activities of phenylsulfonamido derivatives

  摘要：

  A number of phenylsulfonamido derivatives have been synthesized and tested for their ability to inhibit: a) thromboxane A2/prostaglandin H-2 (TXA2/PGH2) mimetic (U46619)- induced guinea pig platelet aggregation; b) aortic ring contraction; and c) binding of a radioiodinated TXA2/PGH2 mimetic (I-BOP) to platelets. In platelets, K(d) values ranged from 9 nM to > 50-mu-M. pK(b) values in aortic rings ranged from 7.63 to 3.66 and in platelets from 7.7 to < 5. A high degree of correlation was observed between the K(d) and pK(b) values found in the 3 systems. Antagonist activity at the TXA2/PGH2 receptor was sensitive to both the substitution pattern of the 2 aromatic rings and the presence of heteroatoms. For 2 of the derivatives (4 and 11) molecular mechanics calculations were performed which indicated subtle structural differences that may account for the > 300-fold difference in potency observed for these analogs at the platelet TXA2/PGH2 receptor.

  DOI：

  10.1016/0223-5234(91)90009-c

文献信息

• Thromboxane A2 receptor antagonists. Synthesis and activities of phenylsulfonamido derivatives
  作者：DE Mais、F Mohamadi、GP Dubé、WL Kurtz、KA Brune、BG Utterback、MM Spees、JA Jakubowski

  DOI：10.1016/0223-5234(91)90009-c

  日期：1991.11

  A number of phenylsulfonamido derivatives have been synthesized and tested for their ability to inhibit: a) thromboxane A2/prostaglandin H-2 (TXA2/PGH2) mimetic (U46619)- induced guinea pig platelet aggregation; b) aortic ring contraction; and c) binding of a radioiodinated TXA2/PGH2 mimetic (I-BOP) to platelets. In platelets, K(d) values ranged from 9 nM to > 50-mu-M. pK(b) values in aortic rings ranged from 7.63 to 3.66 and in platelets from 7.7 to < 5. A high degree of correlation was observed between the K(d) and pK(b) values found in the 3 systems. Antagonist activity at the TXA2/PGH2 receptor was sensitive to both the substitution pattern of the 2 aromatic rings and the presence of heteroatoms. For 2 of the derivatives (4 and 11) molecular mechanics calculations were performed which indicated subtle structural differences that may account for the > 300-fold difference in potency observed for these analogs at the platelet TXA2/PGH2 receptor.