4-(N-methyl-N-phenylacetylamino)-4H-1,2,4-triazole | 33980-43-7

• 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: 4-(N-methyl-N-phenylacetylamino)-4H-1,2,4-triazole
• 英文别名: 4-N-methyl phenylacetylamino-4H-1,2,4-triazole；N-methyl-2-phenyl-N-[1,2,4]triazol-4-yl-acetamide；N-methyl-2-phenyl-N-(4H-1,2,4-triazol-4-yl)acetamide；N-methyl-2-phenyl-N-(1,2,4-triazol-4-yl)acetamide
• CAS: 33980-43-7
• 化学式: C₁₁H₁₂N₄O
• 分子量: 216.242
• InChiKey: NGQLBHRYXFKEEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 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：
  51
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(N-methyl-N-phenylacetylamino)-4H-1,2,4-triazole 在 sulfur 作用下， 以 吡啶 、 硝基甲烷 为溶剂， 反应 6.25h， 生成 acide (4-N-methyl phenylacetylamino-2,3-dihydro-3-thioxo-4H-1,2,4-triazol-2-yl)acetique
  参考文献：
  名称：

  Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques

  摘要：

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.

  DOI：

  10.1016/0223-5234(92)90003-j
• 作为产物：
  描述：

  4-(methylamino)-1,2,4-triazole 、 苯乙酰氯 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以65%的产率得到4-(N-methyl-N-phenylacetylamino)-4H-1,2,4-triazole
  参考文献：
  名称：

  Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques

  摘要：

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.

  DOI：

  10.1016/0223-5234(92)90003-j

文献信息

• Evaluation of the Inhibitory Activity on Serine and Aspartic Proteases of 4-Amino-4H-1,2,4-triazole and 5-Aminothiazole Derivatives Structurally Related to β-Lactam Antibiotics
  作者：Anne-Cécile Vilain、Bernard Pirotte、Isabelle Vergely、Nicole Boggetto、Bernard Masereel、Marc Schynts、Jacques Delarge、Michèle Reboud-Ravaux

  DOI：10.1111/j.2042-7158.1993.tb05577.x

  日期：2011.4.12

  5-aminothiazole have been examined for their inhibitory potential towards serine and aspartic proteases. Upon prolonged incubation with enzyme, the phenylacetylaminothiazolium salts exhibit progressive, time-dependent inhibition of chymotrypsin according to a first-order process. The formation of a tetrahedral transition state-like complex by attack of the active-site serine at the C2-position of the pseudobase

  已经研究了二十种新的4-氨基-4H-1,2,4-三唑和5-氨基噻唑的衍生物对丝氨酸和天冬氨酸蛋白酶的抑制潜力。与酶长时间孵育后，苯乙酰氨基噻唑鎓盐根据一阶过程显示出对胰凝乳蛋白酶的进行性，时间依赖性抑制。噻唑鎓假碱基形式的C2-位上的活性位丝氨酸的攻击形成四面体过渡态样复合物可能是观察到的作用的原因。三唑盐似乎是该酶的简单竞争性抑制剂，在mM范围浓度下有效。在三唑系列中也获得了对胰蛋白酶和胃蛋白酶的不良抑制作用。尽管它们与β-内酰胺类类似，
• Synthèse, étude théorique et évaluation biologique de dérivés du 4-amino-4H-1,2,4-triazole analogues des antibiotiques β-lactamiques
  作者：B Pirotte、G Dive、J Delarge、B Masereel、L Dupont、L Thunus、M Schynts、J Coyette、JM Frère

  DOI：10.1016/0223-5234(92)90003-j

  日期：1992.4

  The synthesis of three classes of potential antibiotic compounds derived from 4-amino-4H- 1,2,4-triazole and related to beta-lactam antibiotics is described. Their originality belongs to the replacement of the beta-lactam carbonyl moiety by another electrophilic centre of the same sp2 geometry. As a result, their interaction with the bacterial target enzyme might lead to the formation of a covalent complex different from the classical acylenzyme. A theoretical study of their structural analogy and their reactivity compared to those of a model beta-lactam justifies their interest in the present context. However, the actual biological results indicate a lack of antibacterial activity.