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Synthesis of diindolylmethane (DIM) bearing thiadiazole derivatives as a potent urease inhibitor

The current study describes synthesis of diindolylmethane (DIM) derivatives based-thiadiazole as a new class of urease inhibitors. Diindolylmethane is natural product alkaloid reported to use in medicinal chemistry extensively. Diindolylmethane-based-thiadiazole analogs (1–18) were synthesized and c...

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Detalles Bibliográficos
Autores principales: Taha, Muhammad, Rahim, Fazal, Khan, Aftab Ahmad, Anouar, El Hassane, Ahmed, Naveed, Shah, Syed Adnan Ali, Ibrahim, Mohamed, Zakari, Zainul Amiruddin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7224224/
https://www.ncbi.nlm.nih.gov/pubmed/32409737
http://dx.doi.org/10.1038/s41598-020-64729-3
Descripción
Sumario:The current study describes synthesis of diindolylmethane (DIM) derivatives based-thiadiazole as a new class of urease inhibitors. Diindolylmethane is natural product alkaloid reported to use in medicinal chemistry extensively. Diindolylmethane-based-thiadiazole analogs (1–18) were synthesized and characterized by various spectroscopic techniques (1)HNMR, (13)C-NMR, EI-MS and evaluated for urease (jack bean urease) inhibitory potential. All compounds showed excellent to moderate inhibitory potential having IC(50) value within the range of 0.50 ± 0.01 to 33.20 ± 1.20 µM compared with the standard thiourea (21.60 ± 0.70 µM). Compound 8 (IC(50) = 0.50 ± 0.01 µM) was the most potent inhibitor amongst all derivatives. Structure-activity relationships have been established for all compounds. The key binding interactions of most active compounds with enzyme were confirmed through molecular docking studies.