N-(4-carboxyphenyl)trifluoromethanesulfonamide | 5433-54-5

• 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-carboxyphenyl)trifluoromethanesulfonamide
• 英文别名: 4-(trifluoromethylsulfonylamido)benzoic acid；4-[(trifluoromethylsulfonyl)amino]benzoic acid；4-{[(Trifluoromethyl)sulfonyl]amino}benzoic acid；4-(trifluoromethylsulfonylamino)benzoic acid
• CAS: 5433-54-5
• 化学式: C₈H₆F₃NO₄S
• mdl: MFCD11649632
• 分子量: 269.201
• InChiKey: KSDPKHIFHRHXGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N-(4-carboxyphenyl)trifluoromethanesulfonamide 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-(trifluoromethanesulfonamido)benzoyl chloride
  参考文献：
  名称：

  动态底物增强，用于鉴定针对一组蛋白质酪氨酸磷酸酶的特定的第二位结合片段

  摘要：

  研究第二个位点： 对磷酸甲酰苯酯被确定为蛋白质酪氨酸磷酸酶（PTP）的通用底物，并用于检查蛋白质的次级结合位点以特异性结合片段。通过在动态连接反应中扩增底物的周转来检测结合片段，并将其发展为高度特异性的PTP抑制剂。

  DOI：

  10.1002/cbic.201100414
• 作为产物：
  描述：

  4-(三氟甲基磺酰氨基)苯甲酸甲酯 在 lithium hydroxide 作用下， 反应 1.0h， 以1.71 g的产率得到N-(4-carboxyphenyl)trifluoromethanesulfonamide
  参考文献：
  名称：

  动态底物增强，用于鉴定针对一组蛋白质酪氨酸磷酸酶的特定的第二位结合片段

  摘要：

  研究第二个位点： 对磷酸甲酰苯酯被确定为蛋白质酪氨酸磷酸酶（PTP）的通用底物，并用于检查蛋白质的次级结合位点以特异性结合片段。通过在动态连接反应中扩增底物的周转来检测结合片段，并将其发展为高度特异性的PTP抑制剂。

  DOI：

  10.1002/cbic.201100414

文献信息

• Convenient synthesis of primary sulfonamides
  作者：Alexander Greenfield、Cristina Grosanu

  DOI：10.1016/j.tetlet.2008.08.054

  日期：2008.10

  An efficient protocol for a one-pot synthesis of mono-sulfonamides has been developed. It features utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide.

  已经开发出一种有效的方案，用于一锅合成单磺酰胺。其特征在于利用过量的磺酰化剂，然后通过碱介导回收伯磺酰胺。
• Substituted peptide derivatives
  申请人：ICI AMERICAS INC.

  公开号：EP0276101A2

  公开（公告）日：1988-07-27

  The invention provides a series of novel substituted peptide derivatives of the formulae la, Ib and Ic (set out hereinafter) and pharmaceutically acceptable salts thereof, in which the radicals A, R1, R2 and R4-R9 have the meanings defined in the following specification. The compounds of formulae la, Ib, and Ic are inhbitors of human leukocytic elastase. The invention also provides pharmaceutical compositions containing a compound of formula la, Ib or Ic, or a pharmaceutically acceptable salt thereof and processes and intermediates for the manufacture of compounds of formulae la, Ib, and Ic.

  本发明提供了一系列新颖的式la、Ib和Ic（如下所述）取代肽衍生物及其药学上可接受的盐，其中自由基A、R1、R2和R4-R9具有以下说明书中定义的含义。 式la、Ib和Ic化合物是人白细胞弹性蛋白酶的抑制剂。 本发明还提供了含有式la、Ib或Ic化合物或其药学上可接受的盐的药物组合物，以及用于制造式la、Ib和Ic化合物的工艺和中间体。
• Peptidic human leukocyte elastase (HLE) inhibitors
  申请人：ZENECA INC.

  公开号：EP0291234A2

  公开（公告）日：1988-11-17

  The invention provides a series of novel heterocyclic ketones of formula I (set out hereinafter) and pharmaceutically acceptable base-addition salts thereof, in which the values of R4, L, A, X and Q have the meanings defined in the following specification. The compounds of formula I are inhibitors of human leukocytic elastase. The invention also provides pharmaceutical compositions containing a compound of formula I, or a pharmaceutically acceptable base-addition salt thereof, and processes and intermediates for the manufacture of compounds of formula I.

  本发明提供了一系列新颖的式 I 杂环酮类化合物（如下所述）及其药学上可接受的碱加成盐，其中 R4、L、A、X 和 Q 的值具有以下说明书中定义的含义。式 I 的化合物是人白细胞弹性蛋白酶的抑制剂。本发明还提供了含有式 I 化合物或其药学上可接受的碱加成盐的药物组合物，以及制造式 I 化合物的工艺和中间体。
• Peptidyl .alpha.-ketoheterocyclic inhibitors of human neutrophil elastase. 3. In vitro and in vivo potency of a series of peptidyl .alpha.-ketobenzoxazoles
  作者：Philip D. Edwards、Mark A. Zottola、Matthew Davis、Joseph Williams、Paul A. Tuthill

  DOI：10.1021/jm00020a011

  日期：1995.9

  A series of peptidyl alpha-ketobenzoxazoles were synthesized and evaluated for their in vitro and in vivo inhibition of human neutrophil elastase (HNE). These compounds inhibit HNE by forming both a covalent bond between the ketone carbonyl carbon atom and the hydroxyl group of Ser-195 and a hydrogen bond between the benzoxazole nitrogen atom and His-57. Appending to the parent benzoxazole ring a variety of substituents which spanned a range of physicochemical properties had only a modest effect on in, vitro potency (K-i = 3-0.4 nM). This apparent lack of a significant effect is believed to result from the fact that any increased ketone carbonyl activation by the ring substituent is counter balanced by a corresponding decrease in the hydrogen-bonding ability of the benzoxazole nitrogen atom. In contrast to the results in vitro, maximizing in vive activity was critically dependent upon the choice of the benzoxazole ring substituent. Several substituted peptidyl alpha-ketobenzoxazoles effectively inhibited HNE-induced lung injury when administered intratracheally 24 h prior to the enzyme.
• Discovery of novel nonpeptide tricyclic inhibitors of ras farnesyl protein transferase
  作者：F. George Njoroge、Ronald J. Doll、Bancha Vibulbhan、Carmen S. Alvarez、W. Robert Bishop、Joanne Petrin、Paul Kirschmeier、Nicholas I. Carruthers、Jesse K. Wong、Margaret M. Albanese、John J. Piwinski、Joseph Catino、V. Girijavallabhan、Ashit K. Ganguly

  DOI：10.1016/s0968-0896(96)00206-4

  日期：1997.1

  A comprehensive structure-activity relationship (SAR) study of novel tricyclic amides has been undertaken. The discovery of compounds that are potent FPT inhibitors in the nanomolar range has been achieved. These compounds are nonpeptidic and do not contain sulfhydryl groups. They selectively inhibit farnesyl protein transferase (FPT) and not geranylgeranyl protein transferase-1 (GGPT-1). They also inhibit H-Ras processing in Cos monkey kidney cells. Copyright (C) 1997 Elsevier Science Ltd.