5-methyl-1-(phenylamino)-1H-[1,2,3]-triazole-4-carboxylic acid hydrazide | 1165474-92-9

• 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: 5-methyl-1-(phenylamino)-1H-[1,2,3]-triazole-4-carboxylic acid hydrazide
• 英文别名: Phenylamino-5-methyl-1h-1,2,3-triazole-4-carbohydrazide；1-anilino-5-methyltriazole-4-carbohydrazide
• CAS: 1165474-92-9
• 化学式: C₁₀H₁₂N₆O
• 分子量: 232.245
• InChiKey: BTKVDKPAGHGOOC-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  97.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-1-(phenylamino)-1H-[1,2,3]-triazole-4-carboxylic acid hydrazide 、 5-硝基糠醛二乙酸酯 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.03h， 以89%的产率得到N'-[(5-nitrofuran-2-yl)methylene]-1-(phenylamino)-5-methyl-1H-1,2,3-triazole-4-carbohydrazide
  参考文献：
  名称：

  Synthesis, antiplatelet and in silico evaluations of novel N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides

  摘要：

  This paper describes the synthesis, antiplatelet and theoretical evaluations of 10 N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides (2a-j). These compounds were synthesized, characterized and screened for their in vitro antiplatelet pro. le against human platelet aggregation using arachidonic acid, adrenaline and ADP as agonists. Among NAH derivatives 2a-j, the compounds 2a, 2c, 2e, 2g and 2h were the most promising molecules with significant antiplatelet activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.053
• 作为产物：
  描述：

  5-methyl-1-(phenylamino)-1H-[1,2,3]-triazole-4-carboxylic acid ethyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-methyl-1-(phenylamino)-1H-[1,2,3]-triazole-4-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives

  摘要：

  In this work, a new series of arysulfonylhydrazine-1H-1,2,3-triazole derivatives were synthesized, and their ability to inhibit the in vitro replication of HSV-1 was evaluated. Among the 1,2, 3-triazole derivatives, 1-[(5 ''-methyl-1 ''-(4'''-fluorophenylamino)-1H-1,2,3-triazol-4 ''-yl) carbonyl]-2-(4'-meth- ylphenylsulfonyl)hydrazine and 1-[(5'-methyl-1'-(2 '',5 ''-dichlorophenylamino)-1H-1,2,3-triazol-4'-yl)carbonyl]-2-(phenylsulfonyl)hydrazine, with IC50 values of 1.30 and 1.26 mu M, respectively, displayed potent activity against HSV-1. Because these compounds have low cytotoxicity, their selectivity indices are high. Under the assay conditions, they have better performance than does the reference compound acyclovir. The structures of all of the compounds were confirmed by one-and two-dimensional NMR techniques (H-1, C-13-APT, COSY-H-1 x H-1 and HETCOR (1)J(CH)) and by elemental analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.007

文献信息

• Antiviral evaluation of N-amino-1,2,3-triazoles against Cantagalo virus replication in cell culture
  作者：Alessandro K. Jordão、Priscila P. Afonso、Vitor F. Ferreira、Maria C.B.V. de Souza、Maria C.B. Almeida、Cristiana O. Beltrame、Daniel P. Paiva、Solange M.S.V. Wardell、James L. Wardell、Edward R.T. Tiekink、Clarissa R. Damaso、Anna C. Cunha

  DOI：10.1016/j.ejmech.2009.04.046

  日期：2009.9

  This paper describes the antiviral evaluation of new N-amino-1,2,3-triazole derivatives, 1-(substituted-phenylamino)-5-methyl-1H-[1,2,3]-triazole-4-carboxylic acid ethyl esters, 3 and 1-(4-substituted-phenylamino)-5-methyl-1H-[1,2,3]-triazole-4-carboxylic acid hydrazides, 4, on Cantagalo virus replication. 1-(4-Fluoro-phenylamino)-5-methyl-1H-[1,2,3]-triazole-4-carboxylic acid hydrazide, 4e, exhibited a significant antiviral effect. Characterization of all compounds was confirmed by IR, H-1 and C-13 spectroscopies and elemental analysis. In addition, molecular structure of 4e was also reported. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides
  作者：Alessandro K. Jordão、Plínio C. Sathler、Vitor F. Ferreira、Vinícius R. Campos、Maria C.B.V. de Souza、Helena C. Castro、Andressa Lannes、André Lourenco、Carlos R. Rodrigues、Murilo L. Bello、Maria C.S. Lourenco、Guilherme S.L. Carvalho、Maria C.B. Almeida、Anna C. Cunha

  DOI：10.1016/j.bmc.2011.07.035

  日期：2011.9

  Tuberculosis treatment remains a challenge that requires new antitubercular agents due to the emergence of multidrug-resistant Mycobacterium strains. This paper describes the synthesis, the antitubercular activity and the theoretical analysis of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides (8a-b, 8e-f, 8i-j and 8n-o) and new analogues (8c-d, 8g-h, 8l-m and 8p-q). These derivatives were synthesized in good yields and some of them showed a promising antitubercular profile. Interestingly the N-acylhydrazone (NAH) 8n was the most potent against the Mycobacterium tuberculosis H37Rv strain (MIC = 2.5 mu g/mL) similar to or better than the current drugs on the market. The theoretical structure-activity relationship study suggested that the presence of the furyl ring and the electronegative group (NO2) as well as low lipophilicity and small volume group at R position are important structural features for the antitubercular profile of these molecules. NMR spectra, IR spectra and elemental analyses of these substances are reported. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis, antiplatelet and in silico evaluations of novel N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides
  作者：Alessandro K. Jordão、Vitor F. Ferreira、Emerson S. Lima、Maria C.B.V. de Souza、Eduardo C.L. Carlos、Helena C. Castro、Reinaldo B. Geraldo、Carlos R. Rodrigues、Maria C.B. Almeida、Anna C. Cunha

  DOI：10.1016/j.bmc.2009.03.053

  日期：2009.5

  This paper describes the synthesis, antiplatelet and theoretical evaluations of 10 N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides (2a-j). These compounds were synthesized, characterized and screened for their in vitro antiplatelet pro. le against human platelet aggregation using arachidonic acid, adrenaline and ADP as agonists. Among NAH derivatives 2a-j, the compounds 2a, 2c, 2e, 2g and 2h were the most promising molecules with significant antiplatelet activity. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives
  作者：Alessandro K. Jordão、Vitor F. Ferreira、Thiago M.L. Souza、Gabrielle G. de Souza Faria、Viviane Machado、Juliana L. Abrantes、Maria C.B.V. de Souza、Anna C. Cunha

  DOI：10.1016/j.bmc.2011.02.007

  日期：2011.3

  In this work, a new series of arysulfonylhydrazine-1H-1,2,3-triazole derivatives were synthesized, and their ability to inhibit the in vitro replication of HSV-1 was evaluated. Among the 1,2, 3-triazole derivatives, 1-[(5 ''-methyl-1 ''-(4'''-fluorophenylamino)-1H-1,2,3-triazol-4 ''-yl) carbonyl]-2-(4'-meth- ylphenylsulfonyl)hydrazine and 1-[(5'-methyl-1'-(2 '',5 ''-dichlorophenylamino)-1H-1,2,3-triazol-4'-yl)carbonyl]-2-(phenylsulfonyl)hydrazine, with IC50 values of 1.30 and 1.26 mu M, respectively, displayed potent activity against HSV-1. Because these compounds have low cytotoxicity, their selectivity indices are high. Under the assay conditions, they have better performance than does the reference compound acyclovir. The structures of all of the compounds were confirmed by one-and two-dimensional NMR techniques (H-1, C-13-APT, COSY-H-1 x H-1 and HETCOR (1)J(CH)) and by elemental analysis. (C) 2011 Elsevier Ltd. All rights reserved.