1-(4-fluorophenylamino)-5-methyl-1H-[1,2,3]-triazole-4-carboxylic acid ethyl ester | 1186385-78-3

• 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: 1-(4-fluorophenylamino)-5-methyl-1H-[1,2,3]-triazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-(4-fluoroanilino)-5-methyltriazole-4-carboxylate
• CAS: 1186385-78-3
• 化学式: C₁₂H₁₃FN₄O₂
• 分子量: 264.259
• InChiKey: MQXWQDGHULSVIX-UHFFFAOYSA-N

物化性质

• 熔点：
  122 °C
• 沸点：
  387.4±52.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenylamino)-5-methyl-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 1-(4-fluorophenylamino)-5-methyl-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
• 作为产物：
  描述：

  重氮基乙酰乙酸乙酯 、 4-氟苯肼盐酸盐 以 甲醇 、 二甲基亚砜 为溶剂， 反应 24.0h， 以30%的产率得到1-(4-fluorophenylamino)-5-methyl-1H-[1,2,3]-triazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Antiviral evaluation of N-amino-1,2,3-triazoles against Cantagalo virus replication in cell culture

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2009.04.046

文献信息

• The differing influence of halides upon supramolecular aggregation through C–X⋯π interactions in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H, F and Cl
  作者：Alessandro K. Jordão、Vitor F. Ferreira、Anna C. Cunha、James L. Wardell、Solange M. S. V. Wardell、Edward R. T. Tiekink

  DOI：10.1039/c2ce25841b

  日期：——

  The presence of localised C–X⋯π [or C–X⋯π(CC)] interactions are shown to be pivotal in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H (1), F (2) and Cl (3). In the absence of halide (1), molecules aggregate into supramolecular chains via alternating ten-membered ⋯HOC2N}2 and 14-membered ⋯HN2C3O}2 synthons. Molecules assemble into a three-dimensional architecture via edge-to-face C–H⋯π(arene) interactions occurring between the phenyl rings. In the presence of halide (i.e. F (2) and Cl (3) in the 4-position of the phenyl ring), two-dimensional arrays are formed by interconnected ten-membered ⋯HOC2N}2 (as seen in 1) and 24-membered ⋯HO⋯NC2OH⋯N4H}2 hydrogen bonded synthons. The latter arrangement allows for the close approach of halide to the 1,2,3-triazole ring and the formation of C–X⋯π interactions which appear to be particularly significant in the case of Cl (3), as evidenced by systematic changes (i.e. elongation) in the geometric parameters within the five-membered ring. In this series of structures, the presence of C–X⋯π interactions is shown to moderate the supramolecular aggregation based on conventional hydrogen bonding.

  在（5-甲基-1-(4-X-芳基氨基)-1H-1,2,3-三唑-4-基）甲醇衍生物的晶体结构中，X = H (1)、F (2) 和 Cl (3)，C–X⋯π（或 C–X⋯π(CC)）相互作用的存在至关重要。在无卤化物（1）的情况下，分子通过交替的十元⋯HOC2N}2和十四元⋯HN2C3O}2合成单元聚集成超分子链。分子通过苯环之间的边缘对边缘C–H⋯π（芳烃）相互作用组装成三维结构。在有卤化物（即苯环4位上的F (2)和Cl (3)）的情况下，二维阵列由相互连接的十元⋯HOC2N}2（如1所示）和二十四元⋯HO⋯NC2OH⋯N4H}2氢键合成单元形成。后一种排列使卤化物能够接近1,2,3-三唑环并形成C–X⋯π相互作用，在Cl (3)的情况下，这种相互作用显得尤为重要，五元环内几何参数的系统变化（即伸长）证明了这一点。在这一系列
• 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.