The present investigation describes the synthesis of a new derivative of thiazolo[3,2-a][1,3]diazepine analogues in continuation to previous patented efforts in this area (compound 1).1,2 The polarity of the free acid metabolite 2, rushes the drug out of the brain and this might be the reason for the ultra-short duration of action. It was thought to replace the ethyl carboxylate moiety of 1 by a methyl group in position 2- or 3- (3). Meanwhile, a bromine atom was introduced to position 2- (4) to increase lipid solubility and to be used as a handle for attaching S bridge to cyclohexyl or phenyl moieties representing alicyclic and aryl functions, (5-7). In order to evaluate the necessity of the 8-oxo function to the pharmacophoric requirements, it was planned to be reduced into 8-hydroxy function (6) or to be removed (7) to find out to what extent it will affect the biological activity. These derivatives (3-7) exhibited a promising and varying range of CNS activities,  including, hypnotic and anticonvulsant activities. A structure activity relationship SAR), which correlates the variation in chemical structure to the activity, was established. These new findings are currently under patency

Synthesis and biological evaluation of some new thiazolodiazepine analogs as CNS active agents

248th National Meeting (2014)

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