SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW HETEROCYCLIC COMPOUNDS CONTAINING THIENO[3,2-c]COUMARIN AND PYRAZOLO[4,3-c]COUMARIN FRAMEWORKS
Adel M. Kamal El-Dean, Remon M. Zaki#, Ahmed A. Geies, Shaban M. Radwan, and Mahmoud S. Tolba
Chemistry department, Faculty of Science, Assiut University, Assiut 71516, Egypt
Received November 21, 2012; in final form, February 26, 2013
Abstract. Reaction of 4-chlorocoumarin-3-carbonitrile with ethyl thioglycolate and ethyl glycinate hydrochloride leads to a series of title products. Hydrazinolysis of amino thienocoumarin carboxylate afforded the hydrazino derivative which underwent various reactions to build new heterocyclic rings containing thienocoumarin moiety. Chloro acetylation of aminoester compound afforded the chloro acetyl amino which underwent nucleophilic substitution reactions various amines. The following treatment with formaldehyde under Mannich conditions afforded the corresponding imidazo derivatives. Reaction of chloroacetylamino with potassium thiocyanate yielded ethylpyrimidothieno coumarin sulfanylacetate which was used as a versatile precursor for synthesis of other heterocycles. On the other hand, reaction of chloro coumarin carbonitrile with hydrazine gave the aminopyrazolocoumaine which reacted with bifunctionally compounds to give the substituted pyrimido derivatives. Diazotization and coupling of aminopyrazole with ethylcyanoacetate yielded ethylaminotriazinopyrazolocoumarine carboxylate. Several of the compounds obtained demonstrated considerable antifungal and antibacterial activity in the in vitro test systems.
Keywords: thienocoumarine, pyrazolocoumarine, pyrimidothienocoumarine, imidazo thienocoumarine, synthesis, anti-microbial activity.
Биоорг.химия 2013, 39 (5): 619-630