nonyl 4-[(aminosulphonyl)oxy]benzoate

• 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: nonyl 4-[(aminosulphonyl)oxy]benzoate
• 英文别名: 4-Sulfamoyloxy-benzoic acid nonyl ester；nonyl 4-sulfamoyloxybenzoate
• 化学式: C₁₆H₂₅NO₅S
• 分子量: 343.444
• InChiKey: MIEAOZZHVJFVJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-壬醇 在 硫酸 、 氨基磺酰氯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.0h， 生成 nonyl 4-[(aminosulphonyl)oxy]benzoate
  参考文献：
  名称：

  Synthesis and biochemical evaluation of some novel benzoic acid based esters as potential inhibitors of oestrone sulphatase

  摘要：

  醇酮硫酸酶是对抗激素依赖性乳腺癌的重要靶点。为了研究已报道的醇酮硫酸酶的明确药效团并继续寻找这种酶的有效抑制剂，我们进行了大量的苯甲酸酯类化合物的合成、生化评价和理化性质测定。在这里，我们报告了我们对一系列直链烷基苯磺酸酯的研究初步结果。使用这些化合物，我们研究了两种理化性质，即logP和pKa的参与。这项研究结果显示，抑制活性与母体化合物的logP之间存在强烈相关性。在研究的化合物系列中，疏水性似乎比pKa更重要，决定了整体的抑制活性。在先前的报告中，我们表明pKa在稳定由磺酸酯基水解产生的苯酚根离子中起重要作用。在这里，我们提出，尽管pKa在考虑广泛的化合物时在确定整体抑制活性中起重要作用，但在设计潜在的醇酮硫酸酶抑制剂时，需要同时考虑疏水性和pKa。

  DOI：

  10.1211/002235702568

文献信息

• Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid
  作者：Chirag K. Patel、Caroline P. Owen、Sabbir Ahmed

  DOI：10.1016/j.bmcl.2003.11.067

  日期：2004.2

  In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess potent inhibitory activity, indeed the cyclooctyl derivative was found to be more potent than 667-COUMATE, which is currently undergoing

  在寻找有效的雌酮硫酸酯酶（ES）抑制剂的过程中，我们进行了一系列4-[（（氨基磺酰基）氧基]苯甲酸的酯的合成和生化评估。研究结果表明，合成的化合物具有有效的抑制活性，实际上环辛基衍生物比目前正在接受临床试验的667-COUMATE更有效。
• Inhibition of estrone sulfatase (ES) by derivatives of 4-[(aminosulfonyl)oxy] benzoic acid
  作者：Sabbir Ahmed、Karen James、Caroline P Owen

  DOI：10.1016/s0960-894x(02)00383-9

  日期：2002.9

  In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of straight chain alkyl esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess greater inhibitory activity when compared to COUMATE, although they were all found to possess lower inhibitory activity with respect to EMATE. Furthermore, the data suggest a strong correlation between logP and IC50 and therefore adds further support to our previous report where we suggested a link between inhibitory activity and hydrophobicity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and biochemical evaluation of some novel benzoic acid based esters as potential inhibitors of oestrone sulphatase
  作者：Caroline Owen、Karen James、Luther Sampson、Sabbir Ahmed

  DOI：10.1211/002235702568

  日期：2010.2.18

  Oestrone sulphatase is an important target in the fight against hormone-dependent breast cancer. In an effort to investigate the reported definitive pharmacophore for oestrone sulphatase and continue our search for potent inhibitors of this enzyme, we have undertaken extensive synthesis, biochemical evaluation and physicochemical property determination of a range of benzoic acid based esters. Here, we report the initial results of our study into a series of straight chain alkyl esters of 4-sulphonylbenzoic acid. Using these compounds, we have investigated the involvement of two physicochemical properties, namely logP and pKa. The results of this study show that there was a strong correlation between the inhibitory activity and the logP of the parent compound. Within the series of compounds studied, hydrophobicity appears to be a more important factor than pKa in determining the overall inhibitory activity. In a previous report, we showed that pKa plays an important role in stabilizing the phenoxide ion resulting from the hydrolysis of the sulphamate group. Here, we propose that although pKa is an important factor in determining the overall inhibitory activity when a wide range of compounds are considered, both hydrophobicity and pKa need to be considered in the design of potential inhibitors of oestrone sulphatase.

  醇酮硫酸酶是对抗激素依赖性乳腺癌的重要靶点。为了研究已报道的醇酮硫酸酶的明确药效团并继续寻找这种酶的有效抑制剂，我们进行了大量的苯甲酸酯类化合物的合成、生化评价和理化性质测定。在这里，我们报告了我们对一系列直链烷基苯磺酸酯的研究初步结果。使用这些化合物，我们研究了两种理化性质，即logP和pKa的参与。这项研究结果显示，抑制活性与母体化合物的logP之间存在强烈相关性。在研究的化合物系列中，疏水性似乎比pKa更重要，决定了整体的抑制活性。在先前的报告中，我们表明pKa在稳定由磺酸酯基水解产生的苯酚根离子中起重要作用。在这里，我们提出，尽管pKa在考虑广泛的化合物时在确定整体抑制活性中起重要作用，但在设计潜在的醇酮硫酸酶抑制剂时，需要同时考虑疏水性和pKa。