Synthesis of 5-arylidine amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamides endowed with potent antioxidants and anticancer activity induces growth inhibition in HEK293, BT474 and NCI-H226 cells

Abstract

A series of imines 5-amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamide derivatives were synthesized from various aromatic aldehydes and substituted with benzoyl acetazolamides under different reaction conditions and were evaluated for their antioxidant and free radical scavenging, antimitotic activity by Allium cepa meristem root model and cytotoxicity activity against HEK 293 (human epidermal kidney cell line), BT474 (breast cancer cell line) and NCI-H226 (lung cancer cell line) by MTT assay. Some of the synthesized compounds showed moderately potent cytotoxicity compared to indisulam. Graphical abstractA series of imines 5-amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamide derivatives (9a–j); 5-amino-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (4a–g); 5-(4-acetamido phenyl sulphonamido)-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (6a–g); and 5-(4-amino phenyl sulphonamido)-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (7a–g) were synthesized from acetazolamide and were investigated for the in vitro anticancer by MTT assay, free radical scavenging and antimitotic activity by Allium cepa root meristem model. Experimental observations indicate that synthesized compounds were moderately potent anticancer agents.

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

“…The most active compounds are: N -({5-[(2-methoxybenzylidene)amino]-1,3,4-thiadiazol-2-yl}sulfonyl)benzamide 28 (CTC 50 = 0.794 µM against breast cancer cell line, CTC 50 —concentration required to reduce viability by 50%) and N -({5-[(furan-2-ylmethylidene)amino]-1,3,4-thiadiazol-2-yl}sulfonyl)benzamide 29 (CTC 50 = 0.913 µM against lung cancer cell line) ( Figure 14 ). None of the tested compounds were found to be as potent as the reference drug [ 24 ].…”

Microwave-Assisted Facile Synthesis, Anticancer Evaluation and Docking Study of N-((5-(Substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) Benzamide Derivatives

“…Unregulated or over-expressed matrix metalloproteinases (MMPs), including stromelysin, collagenase and gelatinase, were implicated in several pathological conditions, including arthritis and cancer. The 1,3,4-thiadozole compounds have been reported to inhibit selectively fibroblast stromelysin-1 [ 24 , 29 ]. In order to predict the binding affinity of our newly synthesized N -((5-(substituted methylene amino)-1,3,4-thiadiazol-2-yl)methyl) benzamide 7 ( a – l ) derivatives into the binding site of fibroblast stromelysin-1, we decided to carry out a molecular docking study.…”

“…Especially, the structure of ‘‘N–C–S’’ in 1,3,4-thiadiazole derivatives can work as the active center, chelate certain metal ions in vivo and show good tissue permeability. The synthesis of novel thiadiazole derivatives and investigation of their chemical and biological behavior have gained more importance in recent decades [ 21 , 22 , 23 , 24 ]. The 1,3,4-thiadozole compounds have been reported to inhibit MMPs [ 25 ].…”

Synthesis, characterization and toxicity studies of pyridinecarboxaldehydes and L-tryptophan derived Schiff bases and corresponding copper (II) complexes

“…Again, HeLa cells were more susceptible to the cytotoxicity of Cu-4pyr.Trp than KCL-22 cells ( Figure 5, B ). Earlier, several Schiff bases were tested in vitro for their cytotoxic activity against different cell lines and the structure activity relationship of compounds was discussed 17 , 31 , 32 . Furthermore, Kril et al .…”