4-amino-N-(5-methyl-3-isoxazolyl)-N-methylbenzenesulfonamide | 51543-31-8

• 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: 4-amino-N-(5-methyl-3-isoxazolyl)-N-methylbenzenesulfonamide
• 英文别名: 4-amino-N-methyl-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
• CAS: 51543-31-8
• 化学式: C₁₁H₁₃N₃O₃S
• 分子量: 267.309
• InChiKey: JRNFDAGFYMJPGU-UHFFFAOYSA-N

物化性质

• 密度：
  1.3486 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-N-(5-methyl-3-isoxazolyl)-N-methylbenzenesulfonamide 、 2',3',4'-三氯苯乙酮 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(3,4-dichlorophenyl)-N-(4-(N-methyl-N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide
  参考文献：
  名称：

  Identification of ML251, a Potent Inhibitor of T. brucei and T. cruzi Phosphofructokinase

  摘要：

  Human African Trypanosomiasis (HAT) is a severe, often fatal disease caused by the parasitic protist Trypanosoma brucei. The glycolytic pathway has been identified as the sole mechanism for ATP generation in the infective stage of these organisms, and several glycolytic enzymes, phosphofructokinase (PFK) in particular, have shown promise as potential drug targets. Herein, we describe the discovery of ML251, a novel nanomolar inhibitor of T. brucei PFK, and the structure-activity relationships within the series.

  DOI：

  10.1021/ml400259d
• 作为产物：
  描述：

  磺胺甲恶唑 、 三甲基碘化亚砜 在 aluminum oxide 、 氢氧化钾 作用下， 反应 0.07h， 以91%的产率得到4-amino-N-(5-methyl-3-isoxazolyl)-N-methylbenzenesulfonamide
  参考文献：
  名称：

  Microwave-Assisted Efficient Methylation of Alkyl and Arenesulfonamides with Trimethylsulfoxonium Iodide and KOH

  摘要：

  A solvent-free synthesis of N-methyl and N,N-dimethylsulfonamides has been achieved by treating the primary and secondary sulfonamides with Me3S+OI- and KOH under microwave irradiation on alumina support.

  DOI：

  10.1080/00397910802045600

文献信息

• Identification of ML251, a Potent Inhibitor of <i>T. brucei and T. cruzi</i> Phosphofructokinase
  作者：Kyle R. Brimacombe、Martin J. Walsh、Li Liu、Montserrat G. Vásquez-Valdivieso、Hugh P. Morgan、Iain McNae、Linda A. Fothergill-Gilmore、Paul A. M. Michels、Douglas S. Auld、Anton Simeonov、Malcolm D. Walkinshaw、Min Shen、Matthew B. Boxer

  DOI：10.1021/ml400259d

  日期：2014.1.9

  Human African Trypanosomiasis (HAT) is a severe, often fatal disease caused by the parasitic protist Trypanosoma brucei. The glycolytic pathway has been identified as the sole mechanism for ATP generation in the infective stage of these organisms, and several glycolytic enzymes, phosphofructokinase (PFK) in particular, have shown promise as potential drug targets. Herein, we describe the discovery of ML251, a novel nanomolar inhibitor of T. brucei PFK, and the structure-activity relationships within the series.
• Microwave-Assisted Efficient Methylation of Alkyl and Arenesulfonamides with Trimethylsulfoxonium Iodide and KOH
  作者：Sarika Malik、Upender K. Nadir、Pramod S. Pandey

  DOI：10.1080/00397910802045600

  日期：2008.8.29

  A solvent-free synthesis of N-methyl and N,N-dimethylsulfonamides has been achieved by treating the primary and secondary sulfonamides with Me3S+OI- and KOH under microwave irradiation on alumina support.