2-[3-fluoro-4-(methanesulfonamido)phenyl]acetic acid | 708261-17-0

• 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: 2-[3-fluoro-4-(methanesulfonamido)phenyl]acetic acid
• CAS: 708261-17-0
• 化学式: C₉H₁₀FNO₄S
• 分子量: 247.247
• InChiKey: AKCDIQMEDFSWRL-UHFFFAOYSA-N

物化性质

• 沸点：
  404.7±55.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.82
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.47
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-叔-丁基苄胺 、 2-[3-fluoro-4-(methanesulfonamido)phenyl]acetic acid 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 N-(4-tert-Butyl-benzyl)-2-(3-fluoro-4-methanesulfonylamino-phenyl)-acetamide
  参考文献：
  名称：

  Analysis of structure–activity relationships for the ‘B-region’ of N-(4-t-butylbenzyl)-N′-[4-(methylsulfonylamino)benzyl]-thiourea analogues as TRPV1 antagonists

  摘要：

  The structure-activity relationships for the 'B-region' of N-(4-t-butylbenzyl)-N '-[4-(methylsulfonylamino)benzyl]thiourea analogues have been investigated as TRPV1 receptor antagonists. A docking model of potent antagonist 2 with the sensor region of TRPV1 is proposed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.006
• 作为产物：
  描述：

  tert-butyl (4-(bromomethyl)-2-fluorophenyl)carbamate 在 盐酸 、 甲醇 作用下， 生成 2-[3-fluoro-4-(methanesulfonamido)phenyl]acetic acid
  参考文献：
  名称：

  N-（3-酰氧基-2-苄基丙基）-N（'）-[4-（甲基磺酰基氨基）苄基]硫脲类似物作为类香草酸受体拮抗剂的“ B区”的结构活性关系分析：N的发现-羟基硫脲类似物，具有有效的镇痛作用。

  摘要：

  研究了强效和高亲和力类香草醇受体（VR1）铅配体N-（3-酰氧基-2-苄基丙基）-N（'）-[4-（甲基磺酰基氨基）苄基]硫脲在B区的结构修饰。用不同的等排官能团取代硫脲。结构活性分析表明，该系列中的A区是决定激动/拮抗活性的主要因素，而与B区无关。与母体硫脲类似物相比，N（C）-羟基硫脲类似物（12、13）在乙酸扭曲试验中显示出出色的镇痛活性。

  DOI：

  10.1016/j.bmcl.2004.02.002

文献信息

• Non-vanillyl resiniferatoxin analogues as potent and metabolically stable transient receptor potential vanilloid 1 agonists
  作者：Hyun-Kyung Choi、Sun Choi、Yoonji Lee、Dong Wook Kang、HyungChul Ryu、Han-Joo Maeng、Suk-Jae Chung、Vladimir A. Pavlyukovets、Larry V. Pearce、Attila Toth、Richard Tran、Yun Wang、Matthew A. Morgan、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmc.2008.11.085

  日期：2009.1

  A series of non-vanillyl resiniferatoxin analogues, having 4-methylsulfonylaminophenyl and fluorophenyl moieties as vanillyl surrogates, have been investigated as ligands for rat TRPV1 heterologously expressed in Chinese hamster ovary cells. Although lacking the metabolically problematic 4-hydroxy substituent on the A-region phenyl ring, the compounds retained substantial agonist potency. Indeed, the 3-methoxy-4-methylsulfonylaminophenyl analog (1) was modestly (2.5-fold) more potent than RTX, with an EC50 = 0.106 nM. Further, it resembled RTX in its kinetics and pattern of stimulation of the levels of intracellular calcium in individual cells, as revealed by imaging. Compound 1 displayed modestly enhanced in vitro stability in rat liver microsomes and in plasma, suggesting that it might be a pharmacokinetically more favorable surrogate of resiniferatoxin. Molecular modeling analyses with selected analogues provide evidence that the conformational differences could affect their binding affinities, especially for the ester versus amide at the B-region. (C) 2008 Elsevier Ltd. All rights reserved.