3-(3-(p-tolyl)ureido)benzoic acid | 74088-14-5

• 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: 3-(3-(p-tolyl)ureido)benzoic acid
• 英文别名: N-p-Tolyl-N'-m-carboxyphenyl-harnstoff；3-{[(4-Methylphenyl)carbamoyl]amino}benzoic acid；3-[(4-methylphenyl)carbamoylamino]benzoic acid
• CAS: 74088-14-5
• 化学式: C₁₅H₁₄N₂O₃
• mdl: MFCD02607190
• 分子量: 270.288
• InChiKey: TYCRWVKJQQIRNE-UHFFFAOYSA-N

物化性质

• 沸点：
  378.9±35.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲苯异氰酸酯 、 间氨基苯甲酸 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以71%的产率得到3-(3-(p-tolyl)ureido)benzoic acid
  参考文献：
  名称：

  Inhibitors of the Cysteine Synthase CysM with Antibacterial Potency against Dormant Mycobacterium tuberculosis

  摘要：

  Cysteine is an important amino acid in the redox defense of Mycobacterium tuberculosis, primarily as a building block of mycothiol. Genetic studies have implicated de novo cysteine biosynthesis in pathogen survival in infected macrophages, in particular for persistent M. tuberculosis. Here, we report on the identification and characterization of potent inhibitors of CysM, a critical enzyme in cysteine biosynthesis during dormancy. A screening campaign of 17?312 compounds identified ligands that bind to the active site with micromolar affinity. These were characterized in terms of their inhibitory potencies and structure-activity relationships through hit expansion guided by three-dimensional structures of enzyme-inhibitor complexes. The top compound binds to CysM with 300 nM affinity and displays selectivity over the mycobacterial homologues CysK1 and CysK2. Notably, two inhibitors show significant potency in a nutrient-starvation model of dormancy of Mycobacterium tuberculosis, with little or no cytotoxicity toward mammalian cells.

  DOI：

  10.1021/acs.jmedchem.6b00674

文献信息

• FAHMY A. F. M.; NADA A. A.; ALY N. F.; ABBASS A., EGYPT. J. CHEM., 1977(1979), 20, NO 3, 259-278
  作者：FAHMY A. F. M.、 NADA A. A.、 ALY N. F.、 ABBASS A.

  DOI：——

  日期：——
• DIARYL UREAS AS CB1 ANTAGONISTS
  申请人：NEUROGEN CORPORATION

  公开号：EP1804785A2

  公开（公告）日：2007-07-11
• USE OF PI3K INHIBITORS FOR THE TREATMENT OF OBESITY, STEATOSIS AND AGEING
  申请人：Fundación Centro Nacional de Investigaciones Oncológicas Carlos III

  公开号：EP2629771B1

  公开（公告）日：2018-08-08
• US8778935B2
  申请人：——

  公开号：US8778935B2

  公开（公告）日：2014-07-15
• [EN] DIARYL UREAS AS CB1 ANTAGONISTS<br/>[FR] DIARYL UREES, ANTAGONISTES DU CB1
  申请人：NEUROGEN CORP

  公开号：WO2006049941A2

  公开（公告）日：2006-05-11

  [EN] Compounds of Formula I are provided. In which the variables are as described herein. Such compounds may be used to modulate CB1 activity in vivo or in vitro, and are particularly useful in the treatment of conditions responsive to CB1 modulation in humans, domesticated companion animals and livestock animals, including appetite disorders, obesity and addictive disorders. Pharmaceutical compositions and methods for using them to treat such disorders are provided, as are methods for using such ligands for receptor localization studies and various in vitro assays.
  [FR] L'invention porte sur des composés de formule (I) dont les variables sont données dans la description. Lesdits composés servent à moduler l'activité du CB1 in vivo ou in vitro, et sont particulièrement utiles pour traiter chez l'homme les états responsables de la modulation du CB1 chez l'homme et les amicaux domestiques, dont les troubles de l'appétit, l'obésité, et la toxicomanie. L'invention porte également sur des préparations pharmaceutiques les contenant, et sur des méthodes de traitement de ces troubles, et d'utilisation de ces ligands dans des études de localisation de récepteurs et différents bioessais in vitro.