4-methylamino-3-nitro-benzenesulfonic acid methylamide | 68502-28-3

• 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-methylamino-3-nitro-benzenesulfonic acid methylamide
• 英文别名: 4-Methylamino-3-nitro-benzolsulfonsaeure-methylamid；N-methyl-4-methylamino-3-nitro-benzenesulfonamide；3-Nitro-4-methylamino-benzolsulfonsaeure-methylamid；4-Chlor-3-nitro-benzolsulfonsaeure-methylamid；2-Nitro-N-methyl-4-methylsulfamoyl-anilin；N-methyl-4-(methylamino)-3-nitrobenzenesulfonamide
• CAS: 68502-28-3
• 化学式: C₈H₁₁N₃O₄S
• mdl: MFCD00089053
• 分子量: 245.259
• InChiKey: RZJVXIKQMVCDHG-UHFFFAOYSA-N

物化性质

• 熔点：
  181 °C
• 沸点：
  420.5±55.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)
• 溶解度：
  >36.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methylamino-3-nitro-benzenesulfonic acid methylamide 在 palladium 10% on activated carbon 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 3-((7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-N-methyl-4-(methylamino)benzenesulfonamide
  参考文献：
  名称：

  Identification of Purines and 7-Deazapurines as Potent and Selective Type I Inhibitors of Troponin I-Interacting Kinase (TNNI3K)

  摘要：

  A series of cardiac troponin I-interacting kinase (TNNI3K) inhibitors arising from 34(9H-purin-6-yl)amino)-N-methyl-benzenesulfonamide (1) is disclosed along with fundamental structure function relationships that delineate the role of each element of 1 for TNNI3K recognition. An X-ray structure of 1 bound to TNNI3K confirmed its Type I binding mode and is used to rationalize the structure activity relationship and employed to design potent, selective, and orally bioavailable TNNI3K inhibitors. Identification of the 7-deazapurine heterocycle as a superior template (vs purine) and its elaboration by introduction of C4-benzenesulfonamide and C7- and C8-7-deazapurine substituents produced compounds with substantial improvements in potency (>1000-fold), general kinase selectivity (10-fold improvement), and pharmacokinetic properties (>10-fold increase in poDNAUC). Optimal members of the series have properties suitable for use in in vitro and in vivo experiments aimed at elucidating the role of TNNI3K in cardiac biology and serve as leads for developing novel heart failure medicines.

  DOI：

  10.1021/acs.jmedchem.5b00931
• 作为产物：
  描述：

  4-氯-N-甲基-3-硝基苯磺酰胺 、 N-甲基脲 生成 4-methylamino-3-nitro-benzenesulfonic acid methylamide
  参考文献：
  名称：

  Lavrishchev,V.A.; Kretov,A.E., Journal of general chemistry of the USSR, 1962, vol. 32, p. 493 - 497

  摘要：

  DOI：

文献信息

• REACTIONS OF p-CHLOROBENZENESULFONIC ACID AND DERIVATIVES. THE σ_P^* CONSTANT OF THE N,N-DIMETHYLSULFON-AMIDO GROUP
  作者：ERNEST L. ELIEL、KENNETH W. NELSON

  DOI：10.1021/jo01364a009

  日期：1955.12
• Identification of Purines and 7-Deazapurines as Potent and Selective Type I Inhibitors of Troponin I-Interacting Kinase (TNNI3K)
  作者：Brian G. Lawhorn、Joanne Philp、Yongdong Zhao、Christopher Louer、Marlys Hammond、Mui Cheung、Harvey Fries、Alan P. Graves、Lisa Shewchuk、Liping Wang、Joshua E. Cottom、Hongwei Qi、Huizhen Zhao、Rachel Totoritis、Guofeng Zhang、Benjamin Schwartz、Hu Li、Sharon Sweitzer、Dennis A. Holt、Gregory J. Gatto、Lara S. Kallander

  DOI：10.1021/acs.jmedchem.5b00931

  日期：2015.9.24

  A series of cardiac troponin I-interacting kinase (TNNI3K) inhibitors arising from 34(9H-purin-6-yl)amino)-N-methyl-benzenesulfonamide (1) is disclosed along with fundamental structure function relationships that delineate the role of each element of 1 for TNNI3K recognition. An X-ray structure of 1 bound to TNNI3K confirmed its Type I binding mode and is used to rationalize the structure activity relationship and employed to design potent, selective, and orally bioavailable TNNI3K inhibitors. Identification of the 7-deazapurine heterocycle as a superior template (vs purine) and its elaboration by introduction of C4-benzenesulfonamide and C7- and C8-7-deazapurine substituents produced compounds with substantial improvements in potency (>1000-fold), general kinase selectivity (10-fold improvement), and pharmacokinetic properties (>10-fold increase in poDNAUC). Optimal members of the series have properties suitable for use in in vitro and in vivo experiments aimed at elucidating the role of TNNI3K in cardiac biology and serve as leads for developing novel heart failure medicines.
• Lavrishchev,V.A.; Kretov,A.E., Journal of general chemistry of the USSR, 1962, vol. 32, p. 493 - 497
  作者：Lavrishchev,V.A.、Kretov,A.E.

  DOI：——

  日期：——