N-[4-methanesulfonylphenyl]acrylamide | 852146-99-7

• 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: N-[4-methanesulfonylphenyl]acrylamide
• 英文别名: N-(4-(methylsulfonyl)phenyl)acrylamide；N-(4-methylsulfonylphenyl)prop-2-enamide
• CAS: 852146-99-7
• 化学式: C₁₀H₁₁NO₃S
• 分子量: 225.268
• InChiKey: GCOCQIBISUCPRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(甲磺酰基)-4-硝基苯 在 铁粉 、 氯化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 20.0h， 生成 N-[4-methanesulfonylphenyl]acrylamide
  参考文献：
  名称：

  Discovery and Structure–Activity Relationship of Potent and Selective Covalent Inhibitors of Transglutaminase 2 for Huntington’s Disease

  摘要：

  Tissue transglutaminase 2 (TG2) is a multifunctional protein primarily known for its calcium-dependent enzymatic protein cross-linking activity via isopeptide bond formation between glutamine and lysine residues. TG2 overexpression and activity have been found to be associated with Huntington's disease (HD); specifically, TG2 is up-regulated in the brains of HD patients and in animal models of the disease. Interestingly, genetic deletion of TG2 in two different HD mouse models, R6/1 and R6/2, results in improved phenotypes including a reduction in neuronal death and prolonged survival. Starting with phenylacrylamide screening hit 7d, we describe the SAR of this series leading to potent and selective TG2 inhibitors. The suitability of the compounds as in vitro tools to elucidate the biology of TG2 was demonstrated through mode of inhibition studies, characterization of druglike properties, and inhibition profiles in a cell lysate assay.

  DOI：

  10.1021/jm201310y

文献信息

• Antihypertensive N-piperazinylalkanoylanilides
  申请人：RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY

  公开号：EP0120558A1

  公开（公告）日：1984-10-03

  N-piperazinylalkanoylanilides of formula wherein is O, 1 or2, each of Rand R, is H or alkyl, and each of R2, R3 and R4 is H, halogen, alkyl, hydroxy-alkyl, alkoxy, aralkoxy, alkylthio, aralkylthio, alkylsulphonyl, alkylsulphenyl, NO2, NH2, alkylamino, acylamino, ureido, alkylureido, alkylsulphonylamino, CF3, acyl, CN, COOH, alkoxycarbonyl, NH2CO, SO3H, guanidinosulphonyl, NH2COO, OH, acyloxy, alkylsulphonyloxy, alkylenedioxy or SO2NR5R6 wherein each of R5 and R6 is H, alkyl, aryl or acyl, and their pharmaceutically acceptable acid addition salts, are antihypertensive agents. They may be prepared by condensing 1-(2-methoxyphenyl)- -piperazine with an alkanoylanilide of formula

  式中的 N-哌嗪基烷酰基苯胺 其中 O、1 或 2，Rand R、中的每一个是 H 或烷基，R2、R3 和 R4 中的每一个是 H、卤素、烷基、羟基烷基、烷氧基、芳基氧基、烷硫基、芳基硫基、烷基磺酰基、烷基磺酰基、NO2、NH2、烷基氨基、酰氨基、脲基、烷基脲基、烷基磺酰基氨基、CF3、酰基、CN、COOH、烷氧羰基、NH2CO、SO3H、胍基磺酰基、NH2COO、OH、酰氧基、烷基磺酰氧基、烷二氧基或 SO2NR5R6（其中 R5 和 R6 各为 H、烷基、芳基或酰基）及其药学上可接受的酸加成盐是降压药。 它们可通过将 1-(2-甲氧基苯基)-哌嗪与式中的烷酰苯胺缩合而制备。
• DECARBOXYLATING BLOCK COPOLYMERS
  申请人：Dogra Kalindi

  公开号：US20100273931A1

  公开（公告）日：2010-10-28

  Linear block copolymers that have at least one hydrophilic block and at least one hydrophobic block, wherein the hydrophilic block of the copolymer has at least one carboxylic acid functionality (or salt thereof) that can readily decarboxylate. These copolymers are useful as binders and/or dispersants in inkjet inks.
• US4940711A
  申请人：——

  公开号：US4940711A

  公开（公告）日：1990-07-10
• Discovery and Structure–Activity Relationship of Potent and Selective Covalent Inhibitors of Transglutaminase 2 for Huntington’s Disease
  作者：Michael E. Prime、Ole A. Andersen、John J. Barker、Mark A. Brooks、Robert K. Y. Cheng、Ian Toogood-Johnson、Stephen M. Courtney、Frederick A. Brookfield、Christopher J. Yarnold、Richard W. Marston、Peter D. Johnson、Siw F. Johnsen、Jordan J. Palfrey、Darshan Vaidya、Sayeh Erfan、Osamu Ichihara、Brunella Felicetti、Shilpa Palan、Anna Pedret-Dunn、Sabine Schaertl、Ina Sternberger、Andreas Ebneth、Andreas Scheel、Dirk Winkler、Leticia Toledo-Sherman、Maria Beconi、Douglas Macdonald、Ignacio Muñoz-Sanjuan、Celia Dominguez、John Wityak

  DOI：10.1021/jm201310y

  日期：2012.2.9

  Tissue transglutaminase 2 (TG2) is a multifunctional protein primarily known for its calcium-dependent enzymatic protein cross-linking activity via isopeptide bond formation between glutamine and lysine residues. TG2 overexpression and activity have been found to be associated with Huntington's disease (HD); specifically, TG2 is up-regulated in the brains of HD patients and in animal models of the disease. Interestingly, genetic deletion of TG2 in two different HD mouse models, R6/1 and R6/2, results in improved phenotypes including a reduction in neuronal death and prolonged survival. Starting with phenylacrylamide screening hit 7d, we describe the SAR of this series leading to potent and selective TG2 inhibitors. The suitability of the compounds as in vitro tools to elucidate the biology of TG2 was demonstrated through mode of inhibition studies, characterization of druglike properties, and inhibition profiles in a cell lysate assay.