bromure de 4-amino-1-tert-butoxycarbonylmethyl-4H-1,2,4-triazolium | 143677-32-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bromure de 4-amino-1-tert-butoxycarbonylmethyl-4H-1,2,4-triazolium
• 英文别名: 4-amino-1-tert-butoxycarbonylmethyl-4H-1,2,4-triazolium bromide；Tert-butyl 2-(4-amino-1,2,4-triazol-4-ium-1-yl)acetate;bromide
• CAS: 143677-32-1
• 化学式: Br*C₈H₁₅N₄O₂
• 分子量: 279.137
• InChiKey: FJLIRPPVNWLBDZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.77
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bromure de 4-amino-1-tert-butoxycarbonylmethyl-4H-1,2,4-triazolium 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 120.42h， 生成 <4-bis<2Z-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetyl>amino-2,3-dihydro-3-oxo-4H-1,2,4-triazol-2-yl>acetate de tert-butyle
  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-氨基-1,2,4-三氮唑 、 溴乙酸叔丁酯 以 硝基甲烷 为溶剂， 反应 6.0h， 以95%的产率得到bromure de 4-amino-1-tert-butoxycarbonylmethyl-4H-1,2,4-triazolium
  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

• 4-Acylamino-4<i>H</i>-1,2,4-triazoles and related structures: new investigations of their chemical and physicochemical properties associated with their particular exocyclic amide function
  作者：Bernard Pirotte、Pascal De Tullio、Bernard Masereel、Marc Schynts、Jacques Delarge、Léon Dupont、Léopold Thunus

  DOI：10.1139/v93-233

  日期：1993.11.1

  The acido-basic behavior of 4-acylamino-4H-1,2,4-triazoles and of the related structures, 4-acylamino-4H-1,2,4-triazolium salts, 4-acylamino-1,2,4-triazoline-3-thiones, and 4-acylamino-1,2,4-triazolin-3-ones, has been compared. Among the triazolium salts examined, the 1-carboxymethyl-4-phenylacetylamino derivative has been selected as a particular triazolium salt bearing two acidic centres, a carboxylic acid group and an exocyclic amide group. This compound has been isolated in three different ionic forms corresponding to different protonation and deprotonation states of the molecule. For these compounds, IR, NMR, and X-ray data were compared and the preferential localization site of the labile proton on the betainic intermediate structure has been discussed. Taking into account that deprotonation of the amide function of 4-acylamino-4H-1,2,4-triazolium salts may introduce a negative pole in the proximity of the strong electrophilic carbon atom in the 2-position of the ring, reactivity of different triazolium salts toward the nucleophilic addition of the hydride ion has been compared. In particular, 4-acylamino-4H-1,2,4-triazolium salts free of alkyl substituent on the amide nitrogen failed to give the corresponding 4-acylamino-Δ2-1,2,4-triazolines after reaction with the hydride ion, while, under the same conditions, the 4-N-methyl derivatives were transformed into this unusual ring system in good yields. In this case, no decrease of reactivity toward the nucleophilic agent was observed since, as a result of the N-al-kylation, no deprotonation of the amide group can occur in these alkaline experimental conditions.

  对4-酰胺基-4H-1,2,4-三唑和相关结构，4-酰胺基-4H-1,2,4-三唑盐，4-酰胺基-1,2,4-三唑烷-3-硫醇和4-酰胺基-1,2,4-三唑烷-3-酮的酸碱性行为进行了比较。在检查的三唑盐中，选择了1-羧甲基-4-苯乙酰胺衍生物作为具有两个酸性中心（羧酸基和外环酰胺基）的特殊三唑盐。该化合物以分子的不同质子化和去质子化状态分离成三种不同的离子形式。对这些化合物进行了红外，核磁共振和X射线数据比较，并讨论了游离质子在间甲基化中间体结构上的优先定位位置。考虑到去质子化4-酰胺基-4H-1,2,4-三唑盐的酰胺功能基可能会在环的2位的强电子亲核碳原子附近引入负极性，比较了不同三唑盐对氢化物离子亲核加成反应的反应性。特别是，不带酰胺氮上烷基取代基的4-酰胺基-4H-1,2,4-三唑盐在与氢化物离子反应后未能产生相应的4-酰胺基-Δ2-1,2,4-三唑烷，而在相同条件下，4-N-甲基衍生物在良好的产率下转化为这种不寻常的环系统。在这种情况下，没有观察到对亲核试剂反应性的降低，因为由于N-烷基化，这些碱性实验条件下酰胺基团不会去质子化。
• 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.