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<p>A series of indazole-based benzamide derivatives (6a–6p) were synthesized via amide cross-coupling reactions and characterized using FTIR, NMR, and HRMS techniques. Density functional theory (DFT) and time-dependent DFT (TD-DFT) studies were performed to investigate the electronic properties of the synthesized compounds. Among the studied derivatives, compound <b>6o</b> exhibited the highest HOMO–LUMO energy gap, indicating enhanced stability, whereas compound <b>6n</b> showed the lowest energy gap, suggesting higher chemical reactivity. Molecular docking studies against VEGFR-2 (PDB ID: 4AG8) identified compounds 6n and 6b as the most promising anticancer candidates, with binding energies of − 11.9 and − 11.52&#xa0;kcal/mol, respectively. Furthermore, docking studies against type III polyketide synthase (PDB ID: 7D41) revealed that compounds <b>6e</b>,<b> 6f</b>, and <b>6o</b> exhibited favorable binding affinities with docking scores of − 9.3, − 8.2, and − 7.5&#xa0;kcal/mol, respectively. All synthesized compounds were evaluated for their anti-mycobacterial activity against <i>Mycobacterium marinum</i>, a validated surrogate model for <i>Mycobacterium tuberculosis</i>, at a concentration of 200 µM. Compound <b>6o</b> displayed the highest growth inhibition (68.4%), identifying it as the most promising anti-tubercular candidate. Although compound <b>6e</b> showed the strongest predicted binding affinity toward the anti-tubercular target, compound <b>6o</b> demonstrated the highest experimental activity, indicating that biological activity is influenced by both target binding and physicochemical properties. Overall, the computational and experimental findings highlight indazole-based benzamide derivatives as promising scaffolds for the development of novel anti-tubercular and anticancer agents.</p>

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Synthesis and computational evaluation of novel indazole-based benzamide derivatives as anti-tubercular agents via DFT, molecular docking studies

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年8月4日

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  • Bandaru Gopi,
  • Ashok Aspatwar,
  • Rebecca Susan Philip,
  • N. M. Karthik,
  • Sundaramoorthy Sarveswari,
  • Yasinalli Tamboli,
  • Vijayaparthasarathi Vijayakumar

摘要

A series of indazole-based benzamide derivatives (6a–6p) were synthesized via amide cross-coupling reactions and characterized using FTIR, NMR, and HRMS techniques. Density functional theory (DFT) and time-dependent DFT (TD-DFT) studies were performed to investigate the electronic properties of the synthesized compounds. Among the studied derivatives, compound 6o exhibited the highest HOMO–LUMO energy gap, indicating enhanced stability, whereas compound 6n showed the lowest energy gap, suggesting higher chemical reactivity. Molecular docking studies against VEGFR-2 (PDB ID: 4AG8) identified compounds 6n and 6b as the most promising anticancer candidates, with binding energies of − 11.9 and − 11.52 kcal/mol, respectively. Furthermore, docking studies against type III polyketide synthase (PDB ID: 7D41) revealed that compounds 6e, 6f, and 6o exhibited favorable binding affinities with docking scores of − 9.3, − 8.2, and − 7.5 kcal/mol, respectively. All synthesized compounds were evaluated for their anti-mycobacterial activity against Mycobacterium marinum, a validated surrogate model for Mycobacterium tuberculosis, at a concentration of 200 µM. Compound 6o displayed the highest growth inhibition (68.4%), identifying it as the most promising anti-tubercular candidate. Although compound 6e showed the strongest predicted binding affinity toward the anti-tubercular target, compound 6o demonstrated the highest experimental activity, indicating that biological activity is influenced by both target binding and physicochemical properties. Overall, the computational and experimental findings highlight indazole-based benzamide derivatives as promising scaffolds for the development of novel anti-tubercular and anticancer agents.