1-(4-methylbenzyl)-4-carboxamido-5-amino-1H-1,2,3-triazole | 99613-60-2

• 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: 1-(4-methylbenzyl)-4-carboxamido-5-amino-1H-1,2,3-triazole
• 英文别名: 5-Amino-1-(4-methylbenzyl)-1,2,3-triazole-4-carboxamide；5-Amino-1-(4-methylbenzyl)-1H-1,2,3-triazole-4-carboxamide；5-amino-1-[(4-methylphenyl)methyl]triazole-4-carboxamide
• CAS: 99613-60-2
• 化学式: C₁₁H₁₃N₅O
• mdl: MFCD08898844
• 分子量: 231.257
• InChiKey: BFZMVZWDHQUUQH-UHFFFAOYSA-N

物化性质

• 熔点：
  223-225 °C
• 沸点：
  496.3±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 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：
  99.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methylbenzyl)-4-carboxamido-5-amino-1H-1,2,3-triazole 在 氨 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 3-(4-Methyl-benzyl)-5-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine
  参考文献：
  名称：

  2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies

  摘要：

  A number of N-6-(N-arylcarbamoyl)-2-substituted-9-benzyl-8-azaadenines, obtained by a modification of the synthetic scheme used to prepare selective A(1) ligands, by only three or two steps, are described. At first we prepared a series of 2-phenyl-9-benzyl-8-azaadenines having as N-6 substituent a variously substituted N-phenylcarbamoyl group. Some of these derivatives demonstrated good affinity towards the A(3) subtype but low selectivity. Compounds having p-CF3, p-F and p-OCH3, as substituents on the phenylcarbamoyl group were selected as lead compounds for the second part of this study. Without modifying the N-6 substituent, which would assure A(3) affinity, we varied the 9 and 2 positions on these molecules to enhance selectivity. Some compounds having a p-methyl group on the 2-phenyl substituent showed a very good affinity and selectivity for the A(3) subtype, revealing the first class of A(3) adenosine receptor selective antagonists with a bicyclic structure strictly correlated to the adenine nucleus. The molecular modelling work, carried out using the DOCK program, supplied two models which may be useful for a better understanding of the binding modes. Both models highlighted the preferred interacting tautomeric forms of the antagonists for human A(1) and A(3) receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.063
• 作为产物：
  描述：

  氰乙酰胺 以69%的产率得到
  参考文献：
  名称：

  BOCHIS, RICHARD J.;TOLMAN, RICHARD;HARRIS, ELBERT

  摘要：

  DOI：

文献信息

• 5-amino or substituted amino 1,2,3-triazoles
  申请人：Merck & Co., Inc.

  公开号：US04721791A1

  公开（公告）日：1988-01-26

  Novel 5-amino or substituted amino 1,2,3-triazoles are disclosed as having anticoccidial activity. The compounds are useful for controlling coccidiosis when administered in minor quantities to animals, in particular to poultry, usually in admixture with animal sustenance.

  小说中披露了具有抗球虫活性的5-氨基或取代氨基1,2,3-三唑化合物。这些化合物在与动物饲料混合后以少量给动物，特别是家禽，通常用于控制球虫病。
• 1,2,3-Triazolo[4,5-<i>e</i>]-1,2,4-triazolo[3,4-<i>c</i>]pyrimidines
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Clementina Manera、Valerio Scartoni

  DOI：10.1002/jhet.5570360514

  日期：1999.9

  Some new 1,2,3-triazolo[4,5-e]-1,2,4-triazolo[3,4-c]pyrimidmes were prepared starting from the corresponding 1,2,3-triazolo[4,5-d]pyrimidines via the formation of the 1,2,4-triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate to give the expected tricyclic derivatives 7, 8 and 9. Intramolecular cyclization of

  一些新的1,2,3-三唑并[4,5- ë ] -1,2,4-三唑并[3，4 - c ^ ] pyrimidmes制备来自相应的1,2,3-三唑并开始并[4,5- d ]嘧啶通过形成1,2,4-三唑环。因此，合适的肼衍生物6用原甲酸三乙酯缩合，原乙酸三乙酯和三乙基orthobenzoate，得到预期三环衍生物7，8和9。乙氧基羰基肼基衍生物10的分子内环化得到在3位带有羟基的三环化合物11。该v在结合测定中针对A 1和A 2A腺苷受体测试了-三唑-三唑并嘧啶衍生物，但它们没有显示任何受体亲和力。
• 5-Amino or substituted amino 1,2,3-triazoles
  申请人：Merck & Co., Inc.

  公开号：US04816469A1

  公开（公告）日：1989-03-28

  Novel 5-amino or substituted amino 1,2,3-triazoles are disclosed as having anticoccidial activity. The compounds are useful for controlling coccidiosis when administered in minor quantities to animals, in particular to poultry, usually in admixture with animal sustenance.

  揭示了具有抗球虫活性的新型5-氨基或取代氨基1,2,3-三唑化合物。这些化合物在与动物食物混合后，通常以微量给予动物，特别是家禽，可用于控制球虫病。
• RIED, WALTER;LAOUTIDIS, JOANNIS, CHEM.-ZTG., 114,(1990) N-8, C. 246-248
  作者：RIED, WALTER、LAOUTIDIS, JOANNIS

  DOI：——

  日期：——
• 5-(Amino or substituted amino)-1,2,3-triazoles
  申请人：Merck & Co., Inc.

  公开号：EP0151528B1

  公开（公告）日：1990-07-04