Functionalization of pyrazolo[1,5-a]pyrazine-Schiff bases for assessing liquid crystalline properties and antimicrobial activity

IF 4.7 2区化学 Q2 CHEMISTRY, PHYSICAL Journal of Molecular Structure Pub Date : 2025-07-15 Epub Date: 2025-02-27 DOI:10.1016/j.molstruc.2025.141889

Vinod Ashtekar , Ranjitsinh C. Dabhi , Vidhi A. Trivedi , Prashant S. Arya , Ashish Patel , Parth Thakor , Bhavesh N. Socha , Chetan B. Sangani , Jay C. Panchal , Abdullah Alarifi , Hemant N. Patel

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Abstract

A series of novel Schiff bases compounds (VSBs) incorporating pyrazolo[1,5-a]pyrazine moieties were synthesized through alkylation, condensation, and esterification with various 4-((4-alkoxybenzylidene)aminobenzoic acids. The mesomorphic properties of these compounds were systematically investigated using polarized optical microscopy and confirmed by differential scanning calorimetry. All synthesized materials exhibited enantiotropic liquid crystalline phases. Compounds with shorter aliphatic chains (VSB₄-VSB₉) nematic phases, whereas those with longer chains (VSB₁₀) predominantly exhibited the SmA as well as nematic mesophase. Density functional theory (DFT) optimization of VSBs for more inhibitor efficiency compared. Additionally, the antimicrobial activity of the VSBs was evaluated, revealing a strong correlation between the length of the alkyl chain and antimicrobial potency. Notably, VSB₁₀, with the longest chain, exhibited the highest docking score against Bacillus subtilis and showed the most significant zone of inhibition against both gram-positive and gram-negative bacteria, indicating its potential as a broad-spectrum antimicrobial agent. These findings underscore the dual functionality of the VSBs, making them potential candidates for advanced liquid crystalline applications and antimicrobial therapies.

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吡唑啉[1,5-a]吡嗪-希夫碱功能化评价液晶性质和抗菌活性

以4-(（4-烷氧基苄基）氨基苯甲酸为原料，通过烷基化、缩合、酯化等反应，合成了一系列含有吡唑[1,5- A]吡嗪基团的新型希夫碱化合物。用偏光显微镜系统地研究了这些化合物的介形性质，并用差示扫描量热法进行了证实。所有合成材料均表现为对映性液晶相。具有较短脂肪链的化合物（VSB4-VSB9）具有向列相，而具有较长脂肪链的化合物（VSB10）主要表现为SmA和向列中间相。密度泛函理论（DFT）优化了VSBs的抑制剂效率。此外，对VSBs的抗菌活性进行了评估，发现烷基链的长度与抗菌效力之间存在很强的相关性。值得注意的是，链最长的VSB10对枯草芽孢杆菌的对接得分最高，对革兰氏阳性菌和革兰氏阴性菌的抑制区均最显著，表明其具有广谱抗菌潜力。这些发现强调了VSBs的双重功能，使其成为先进液晶应用和抗菌治疗的潜在候选者。

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.