(5-methyl-1-(phenylamino)-1H-1,2,3-triazol-4-yl)methanol | 1421925-61-2

• 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-triazol-4-yl)methanol
• 英文别名: 5-Methyl-1-(phenylamino)-1h-1,2,3-triazol-4-yl-methanol；(1-anilino-5-methyltriazol-4-yl)methanol
• CAS: 1421925-61-2
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: YDKQQWVESRGBCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-methyl-1-(phenylamino)-1H-1,2,3-triazol-4-yl)methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 以80%的产率得到1-(phenylamino)-5-methyl-1H-[1,2,3]-triazole-4-carbaldehyde
  参考文献：
  名称：

  Exploring 1,2,3-triazole derivatives by using in vitro and in silico assays to target new antifungal agents and treat Candidiasis

  摘要：

  Candidiasis is a serious public health problem that currently affects not only immunodeficient patients with predisposing conditions, but also immunocompetent individuals. Thus, the search for new antifungal agents is required also due to the emergence of resistant strains and to the side effects of the available drugs. The aim of this study is to evaluate the in vitro antifungal profile of nine synthetic 1,2,3-triazole derivatives against four Candida species of medical importance (C. albicans, C. tropicalis, C. parapsilosis, and C. krusei), as well as to identify their in silico structure-activity relationship. Interestingly, the antifungal susceptibility tests showed the compound 5-methyl-1-(phenylamino)-1H-1,2,3-triazol-4-yl-methanol (2b) with the lowest minimal inhibitory concentration value against C. albicans strain (MIC = 8 mu g/mL) similar to other promissing compounds described in the literature. According to our in silico evaluation, some stereoelectronic properties (e.g., higher values of log S and lowest unoccupied molecular orbital energy and lower number of atoms, rotatable bonds and Hydrogen bond acceptors) were correlated with the antifungal activity detected. This series reinforced the potential of 1,2,3-triazole as a promising nucleus in the search for new antifungals and may help on designing new drugs for candidiasis.

  DOI：

  10.1007/s00044-017-1789-x
• 作为产物：
  描述：

  5-methyl-1-(phenylamino)-1H-[1,2,3]-triazole-4-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以50%的产率得到(5-methyl-1-(phenylamino)-1H-1,2,3-triazol-4-yl)methanol
  参考文献：
  名称：

  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

  摘要：

  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

  DOI：

  10.1039/c2ce25841b