Synthesis, docking and evaluation of antioxidant and antimicrobial activities of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidines

• Published in: European journal of medicinal chemistry Vol. 75; pp. 195 - 202
• Main Authors: Kotaiah, Y., Nagaraju, K., Harikrishna, N., Venkata Rao, C., Yamini, L., Vijjulatha, M.
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 21.03.2014; Elsevier
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antimicrobial activities; Antioxidant properties; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Bacteria - drug effects; Bacterial Infections - drug therapy; Benzene Derivatives - chemical synthesis; Benzene Derivatives - chemistry; Benzene Derivatives - pharmacology; Chemistry, Medicinal; Fungi - drug effects; Humans; Life Sciences & Biomedicine; Microbial Sensitivity Tests; Molecular docking; Molecular Docking Simulation; Mycoses - drug therapy; Organoselenium Compounds - chemical synthesis; Organoselenium Compounds - chemistry; Organoselenium Compounds - pharmacology; Pharmacology & Pharmacy; Pyrimidines - chemical synthesis; Pyrimidines - chemistry; Pyrimidines - pharmacology; Science & Technology; Selenopheno[2,3-d]pyrimidines; Synthesis; Thiadiazoles - chemical synthesis; Thiadiazoles - chemistry; Thiadiazoles - pharmacology; Triazolothiadiazoles; Selenopheno[2,3-d]pyrimidines; Antioxidant properties; Synthesis; Antimicrobial activities; Triazolothiadiazoles; Molecular docking; SCAVENGING PROPERTIES; FACILE SYNTHESIS; PHARMACOLOGICAL-ACTIVITIES; CANCER; SELENIUM
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2014.01.006

A series of 1,2,4-(triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidines (10a–j) were synthesized with various substituted anilines and benzoic acids. Structures of newly synthesized compounds were established by IR, 1H &13C NMR and LC–MS spectral data. The antioxidant activity of the synthesized compounds was evaluated by DPPH, NO and H2O2 radical scavenging methods. The newly synthesized compounds were evaluated for their antimicrobial activity against Gram +ve and Gram −ve bacteria and antifungal activity by well diffusion method. Compounds 10d, 10h and 10i showed promising antioxidant, antibacterial as well as antifungal activity and these were found to be the most potent activity molecules when compared with that of standard drugs. Molecules docking studies have been performed on Staphylococcus aureus (SA) of Gram +ve bacteria. Synthesis of a novel series of substituted 1,2,4-(triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidine derivatives (10a–j). Compounds 10d, 10h and 10i showed potent antimicrobial and significant radical scavenging activities. [Display omitted] •A series of 1,2,4-(triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidine derivatives have been synthesized.•Some compounds 10d, 10h and 10i have showed potent antimicrobial and antioxidant activity than the standard drugs.•The SAR studies showed that the functional groups presented on phenyl ring plays an important role.•Docking studies were performed on DHSS of Staphylococcus aureus bacteria.•10i showed good interactions with the active site amino acids of the four proteins.