Synthesis and antioxidant activity of 2-methylthio-pyrido[3,2-e][1,2,4] triazolo[1,5-a]pyrimidines

Abstract

A series of 2-methylthio-pyrido-triazolopyrimidines (1-17) were prepared by the reaction of dimethyl-N-cyanoimidodithiocarbonate with hydrazinopyridine carboxylic acid as starting reactants. Their chemical structures were affirmed with HREI-MS, IR and NMR analyses. The target compounds (1-17) were evaluated for their antioxidant activity using 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging, ferric reduction antioxidant power (FRAP) and reducing power capability (RPC). The results revealed that some pyrido-triazolopyrimidines showed good activity as antioxidant agents, in particular, compounds 12 and 15 were found to possess good antioxidant activity. Butylated hydroxyl toluene (BHT) was used as reference drug.

Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

“…Throughout our research, we have noticed that the 1,2,4-triazole or 1,2,3-triazole derivatives showed antioxidant properties [28][29][30][31][32][33][34][35] and demonstrated cytotoxic activity as well. In a previous work, the molecular hybridization technique was employed to incorporate the triazole unit with isothiocyanate and substituted benzylidene groups into a single molecule; the resulting targets have the potential to exhibit potent antiproliferative activity against HCT-116 and MCF-7 human cancer cell lines and showed very weak cytotoxicity against normal cells [35].…”

“…The Schiff bases of 4-aminotriazole derivatives demonstrated potential free radical scavenger effects, whereas the N-substituted triazole attached indole/chalcone hybrids and 1,2,4-triazole-3-thiones reported to exhibit significant antioxidant activity on DPPH radicals and were found to be potent anticancer agents [30,31]. Incorporation of 1,2,4-triazole ring with quinazoline and pyridopyrimidine units was proved to be favorable for the antioxidant and cytotoxicity activities [32][33][34].…”

Structural cytotoxicity relationship of 2-phenoxy(thiomethyl)pyridotriazolopyrimidines: Quantum chemical calculations and statistical analysis

“…The synthetic methodology for target pyridotriazolopyrimidines ( Table 1 and Scheme 1) has been previously described [10,11]. As illustrated in Table 2, the in vitro cytotoxicity of pyridotriazolopyrimidines was evaluated against A549, HepG2, MCF-7, and WRL 68 cells using the MTT assay.…”

“…For HepG2, IP has the strongest effect with a regression coefficient of 13.34. For MCF-7, the electronegativity displays the strongest contribution with a moderate effect on electrophilicity contribution (equation (11)). Hardness (with a negative contribution of 8.70) shows the strongest effect on the activity of the tested compounds against WRL68 (equation (12)).…”

“…In contrast, 1,2,4-triazoles are associated with various pharmacological activities, and a large number of predominant triazole drugs have been successfully developed and prevalently used in the treatment of various microbial infections such as fluconazole, posaconazole, and itraconazole (antifungal). Combining these three structure features in one molecule (pyridotriazolopyrimidine) has showed significant pharmacological efficiency as fungicidal, herbicidal, antidiabetic, and antioxidant agents [6][7][8][9][10][11].…”