A series of novel 5-(3,5-disubstituted-1H-indol-2-yl)-2,3-dimethyl-1-phenyl-2,6-dihydro-1H-pyrazolo[4,3-e][1,2,4]triazines (3a-l) were synthesized in single step from 3,5-disubstituted indole-2-carbohydrazide and 4-aminoantipyrine under acidic conditions with excellent yields. The various spectroscopic methods were used to prove the formation of all these products. The compounds 3a, 3b, 3e, 3f, 3i and 3j exhibited excellent antibacterial and antifungal activities with an MIC value of 3.125 µg/ml against the tested pathogens and anti-tuberculosis inhibitory potential against M. tuberculosis which is equivalent to standard drug. The antidiabetic activity of the compounds 3a and 3b showed the maximum potential as glucosidase inhibitors with IC₅₀ = 47.21 μg/ml and IC₅₀ = 48.36 μg/ml, respectively. The physicochemical characteristics like ADMET, drug-likeness and bioactivity scores for these molecules were also disclosed. To comprehend the electronic behavior of compound 3a, density functional theory estimations at the DFT/B3LYP level via 6-31G++ (d, p) have been carried out to replicate the structure and geometry. The first-order hyperpolarizability calculation was used to calculate the nonlinear visual feature of compound 3a. The charge transfer interface among the structure is elucidated by the estimated HOMO–LUMO analysis. Further, molecular docking studies were carried out for synthesized compounds with human maltase-glucoamylase (PDB: 2QMJ).

Graphical abstract

中文翻译：

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吲哚类吡唑并三嗪的合成、光谱分析、DFT计算、生物潜力和分子对接研究

一系列新型5-(3,5-二取代-1H-吲哚-2-基)-2,3-二甲基-1-苯基-2,6-二氢-1H-吡唑并[ 4,3 -e] [1,2,4] 三嗪 ( 3a-l ) 在酸性条件下由 3,5-二取代吲哚-2-碳酰肼和 4-氨基安替比林一步合成，收率高。各种光谱方法被用来证明所有这些产品的形成。化合物3a、3b、3e、3f、3i和3j表现出优异的抗菌和抗真菌活性，对受试病原体的MIC值为3.125 µg/ml，对结核分枝杆菌的抗结核抑制潜力与标准药物相当。化合物的抗糖尿病活性3a和3b显示出作为葡糖苷酶抑制剂的最大潜力，分别为 IC ₅₀  = 47.21 μg/ml 和 IC ₅₀  = 48.36 μg/ml。还公开了这些分子的理化特性，如 ADMET、药物相似性和生物活性评分。为了理解化合物3a的电子行为，通过 6-31G++ (d, p) 在 DFT/B3LYP 水平上进行了密度泛函理论估计，以复制结构和几何形状。一级超极化率计算用于计算化合物3a的非线性视觉特征. 通过估计的 HOMO-LUMO 分析阐明了结构之间的电荷转移界面。此外，对与人麦芽糖酶-葡糖淀粉酶 (PDB: 2QMJ) 合成的化合物进行了分子对接研究。

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