N-[2-(4-nitrophenyl)ethyl]-4-methylbenzenesulfonamide | 111437-16-2

• 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-[2-(4-nitrophenyl)ethyl]-4-methylbenzenesulfonamide
• 英文别名: N-(4-nitro-phenethyl)-toluene-4-sulfonamide；N-(4-Nitro-phenaethyl)-toluol-4-sulfonamid；4-methyl-N-[2-(4-nitro-phenyl)-ethyl]-benzenesulfonamide；4-Methyl-N-[2-(4-nitro-phenyl)-ethyl]benzenesulfonamide；4-methyl-N-[2-(4-nitrophenyl)ethyl]benzenesulfonamide
• CAS: 111437-16-2
• 化学式: C₁₅H₁₆N₂O₄S
• 分子量: 320.369
• InChiKey: XUUNFYIVSCXXRE-UHFFFAOYSA-N

物化性质

• 沸点：
  513.8±60.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-(4-nitrophenyl)ethyl]-4-methylbenzenesulfonamide 在 钯 作用下， 以 甲醇乙酸乙酯 为溶剂， 以to afford 0.368 g of the desired product的产率得到N-(4-aminophenethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Phenethylamino sulfamic acids

  摘要：

  化合物I的公式：1在治疗蛋白酪氨酸磷酸酶（PTPase）介导的疾病，如糖尿病方面是有效的。

  公开号：

  US20040167183A1
• 作为产物：
  描述：

  对硝基苯乙腈 在 sodium tetrahydroborate 、 三氟化硼 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-[2-(4-nitrophenyl)ethyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Chemistry of synthetic receptors and functional group arrays. 7. Molecular armatures. Synthesis and structure of Troeger's base analogs derived from 4-, 2,4-, 3,4-, and 2,4,5-substituted aniline derivatives

  摘要：

  DOI：

  10.1021/jo00236a020

文献信息

• Phenethylamino sulfamic acids
  申请人：The Procter & Gamble Company

  公开号：US20040167183A1

  公开（公告）日：2004-08-26

  Compounds of formula (I): 1 are effective in the treatment of protein tyrosine phosphatase (PTPase) mediated disorders such as diabetes.

  公式（I）的化合物在治疗蛋白酪氨酸磷酸酶（PTPase）介导的疾病，如糖尿病方面具有有效性。
• [EN] PHENETHYLAMINO SULFAMIC ACIDS<br/>[FR] ACIDES SULFAMIQUES DE PHENETHYLAMINO
  申请人：PROCTER & GAMBLE

  公开号：WO2004074238A1

  公开（公告）日：2004-09-02

  Compounds of formula (I): (I)are effective in the treatment of protein tyrosine phosphatase (PTPase) mediated disorders such as diabetes.
• Synthesis and Evaluation of Potent and Selective β₃ Adrenergic Receptor Agonists Containing Acylsulfonamide, Sulfonylsulfonamide, and Sulfonylurea Carboxylic Acid Isosteres
  作者：David E. Uehling、Kelly H. Donaldson、David N. Deaton、Clifton E. Hyman、Elizabeth E. Sugg、David G. Barrett、Robert G. Hughes、Barbara Reitter、Kim K. Adkison、Mary E. Lancaster、Frank Lee、Robert Hart、Mark A. Paulik、Bryan W. Sherman、Timothy True、Conrad Cowan

  DOI：10.1021/jm0101500

  日期：2002.1.1

  Starting from phenethanolamine aniline leads 3a and 3b, we have identified a series of functionally potent and selective beta(3) adrenergic receptor (AR) agonists containing acylsulfonamide, sulfonylsulfonamide, or sulfonylurea groups within the aniline phenethanolamine series. In beta(3) beta(2), and beta(1) AR cAMP functional assays, 3a and other right-hand side (RHS) carboxylate analogues were found to be full agonists that were modestly selective against beta(1) or beta(2) ARs, while analogues lacking RHS acid functionality were active at beta(3) AR but not selective. Replacement of the carboxylate with acylthiazole and acylmethylsulfone gave potent, but only modestly selective, compounds. Increasing the size of the RHS sulfonamide substituent with phenyl or p-toluene afforded compounds with good potency and functional selectivity (beta(3) AR pEC(50) greater than 8; beta(1) and beta(2) AR selectivity greater than 40- and 500-fold, respectively). Our SAR studies suggest that the potency and selectivity profile of the best analogues reported here is a result of both the steric bulk and acidity of the RHS sulfonamide NH group. Although all of the analogues had a pharmacokinetic half-life of less than 2 h, acylsulfonamides 43 and 44 did show moderately low clearance in dogs. These two compounds were further evaluated by thermographic imaging in mice and were found to produce a robust thermogenic response via oral administration.
• Chemistry of synthetic receptors and functional group arrays. 7. Molecular armatures. Synthesis and structure of Troeger's base analogs derived from 4-, 2,4-, 3,4-, and 2,4,5-substituted aniline derivatives
  作者：Irving Sucholeiki、Vincent Lynch、Ly Phan、Craig S. Wilcox

  DOI：10.1021/jo00236a020

  日期：1988.1