Abstract:
This dissertation; Synthesis and biological evaluation of 1,2,3-benzotriazin
4(3H)-one based compounds comprises easy preparation of new compounds and
study of their enzyme inhibition assay. Three series of 1,2,3-benzotriazin-4(3H)-one
sulfonamide / carboxamides were synthesized in good to excellent yields. For the
preparation of first series isatin was converted to isatoic anhydride, then reacted with
sulfanilic acid followed by diazotization to cyclize to 4-(4-oxobenzo[d][1,2,3]triazin
4(3H)-yl)benzenesulfonic acid. The acid was directly converted to series of
sulfonamides by using 1,3,5-trichlorotriazine:N,N-dimethylformamide (TCT: DMF)
adduct at room temperature. The reaction was found successful only for electron rich
anilines.
For the second series, isatin was converted to of 4-(4
oxobenzo[d][1,2,3]triazin-3(4H)-yl)butanoic acid through isatoic anhydride. Then N
(4-(1H-benzotriazol-1-yl)-4-oxobutyl)benzo[1,2,3]triazin-4(3H)-one was synthesized
by reacting the acid with thionyl chloride and benzotriazole. Further at room
temperature benzotriazole moiety was replaced with different amines and anilines to
afford amide derivatives.
In another series 6-amino-N-alkyl-1,2,3-benzotriazin-4(3H)-ones were used to
prepare sulfonamide derivatives by reaction with different sulfonyl chlorides.
All the prepared compounds were evaluated for their enzyme inhibition
potency. α-Glucosidase, Urease and Acetylcholinesterase were used to study. Results
indicated that most of the compounds have potential to inhibit α-glucosidase better as
compared to standard drugs. Anti-urease results showed fair to good inhibition
activity but less than refernce compound; thiourea. In case of acetylcholinesterase, none of the compound found active.
