Synthesis and anticonvulsant evaluation of 3-substituted-4-(4-hexyloxyphenyl)-4H-1,2,4-triazoles

Abstract

A series of 3-substituted-4-(4-hexyloxyphenyl)-4H-1,2,4-triazole derivatives (3a-s) were synthesized as open-chain analogues of 7-hexyloxyl-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinolines (1c) using 4-hexyloxyaniline, acyl hydrazines, and dimethoxy-N,N-dimethylmethanamine as the starting material. Their anticonvulsant activities were evaluated by the maximal electroshock test (MES test) and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox). MES test showed that all open-chain compounds exhibited strong anticonvulsant activity and lower neurotoxicity, and that some possessed obviously stronger activity than compound 1c. Compound 3d, 3-propyl-4-(4-hexyloxyphenyl)-4H-1,2,4-triazole was found to be the most potent with an ED 50 value of 5.7 mg/kg and protective index (PI = TD 50 /ED 50 ) value of 11.5, which was much greater than that of the prototype drug phenytoin (PI = 6.9).

Metal-based ethanolamine-derived compounds: a note on their synthesis, characterization and bioactivity

“…the compounds (9), (10) and (12)- (16) and the results are reported in Table 5. The MIC values of these compounds fall in the range 23.11-46.62 g/mL.…”

“…The Schiff bases are characterized by an imine group and are formed as a condensation product 2 of primary amine with an aldehyde or ketone in the presence of a dehydrating agent such as MgSO 4 . A number of Schiff's base metal complexes have displayed bioactivity as antibacterial 3,4 , antifungal 5 , anticancer 6,7,8 , anti-inflammatory 9 , anticonvulsant 10 , antiviral 11 and analgesic 12 agents. Although metal-based ethanolamines have historically been subjected of many investigations 13,14 due to their use as buffers 15 , catalysts 16 , inhibitors 17 , ion exchangers 18 , electroplating and dyes 19 , now they are garnering attention for their biological 20 role in plant growth 21 regulation, bacterial and fungal metabolism and as a cytotoxic agent 22 .…”

In vitro antibacterial, antifungal and cytotoxic activities of some triazole Schiff bases and their oxovanadium(IV) complexes

“…1,2,4-Triazoles have been known for a potential use in a wide variety of therapeutically interesting drugs including CNS stimulant, anti-anxiety 2 and also antimycotic compounds such as fluconazole, intraconazole and voriconazole 3 . In view of the significant therapeutic uses, the chemistry of 1,2,4-triazoles represents an important class of compounds owing to their synthetic and effective biological properties like antibacterial 4 , antifungal 5 , anticonvulsant 6 , antiproliferative 7 , antitumor 8 , antitubercular 9 , anticancer 10 , anti HIV 11 and antiviral 12 . Vanadium chemistry has established its strong role as antimicrobial 13 , anti-tumor 14 , anti-leukemic 15 , spermicidal 16 , anti-amoebic 17 , antioxidant 18 and osteogenic 19 activity in bioinorganic chemistry.…”

Design, synthesis andin vitrobactericidal/fungicidal screening of some vanadyl(IV)complexes with mono- and di-substituted ONS donor triazoles

“…Metal complexes have been the best choice so far in designing these candidates with remarkable biological potentials [1][2][3] . Variety of triazole derivatives represent an interesting class of compounds showing diversified clinical and pharmacological applications such as anti-bacterial 4 , anti-fungal 5 , anti-tumor 6 , anti-cancer 7 , anti-inflammatory 8 , anti-convulsant 9 , anti-proliferative 10 and analgesic properties 11 . Advances in medicinal properties of vanadium metal complexes have led to designing and use of its bioactive potential in metal-based drugs 12 .…”