title: Synthesis and antimicrobial activity of new heterocyclic compounds containing thieno[3,2-c] coumarin and pyrazolo[4,3-c] coumarin frameworks.
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 hydrazine 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 Ghloroacetylamino 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 carbo nitrile 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.
authors.affiliation: Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt.
authors.forename: Adel M Kamal
authors.initials: AM
authors.lastname: El-Dean
authors.forename: Remon M
authors.initials: RM
authors.lastname: Zaki
authors.forename: Ahmed A
authors.initials: AA
authors.lastname: Geies
authors.forename: Shaban M
authors.initials: SM
authors.lastname: Radwan
authors.forename: Mahmoud S
authors.initials: MS
authors.lastname: Tolba
mesh_terms: D000900:Anti-Bacterial Agents / Q000008:administration & dosage / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry; D001419:Bacteria / Q000187:drug effects; D003374:Coumarins / Q000008:administration & dosage / Q000138:chemical synthesis*; D005658:Fungi / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000008:administration & dosage / Q000138:chemical synthesis; D008826:Microbial Sensitivity Tests; D011720:Pyrazoles / Q000008:administration & dosage / Q000138:chemical synthesis*
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D003374:Coumarins; D006571:Heterocyclic Compounds; D011720:Pyrazoles; C030123:coumarin