Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry, Pharmaceutical Sciences and Computational Chemistry

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Abstract

Synthesis, characterization and antimicrobial activity of some 2-(propen-1-one) aryl 3-substituted phenothiazine

Author(s): Ujwala Sawarkar, Meghasham Narule, Mahendra Choudhari

1-(4-phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one 1was prepared by condensation of 4-hydroxy benzaldehyde with acetophenone by Claisen-Schmidt Condensation. When 1-(4-phenyl)-3-(4-hydroxyphenyl)-2-propen-1-one combines with substituted anilines it gives 1-(4-phenyl)-3-(4’-aminophenyl) aryl-2-propen-1-one 2. When 2 undergo cyclization with sulphur and iodine gives 2-(propen-1-one) aryl-3-substituted phenothiazines 3. All these reactions are carried out under microwave irradiation in microwave oven. Chalcones (α,β ) unsaturated aromatic ketone are important intermediate product in organic synthesis. Phenothiazine is an organic compound that occurs in various antipsychotic and antihistaminic drugs. The compound is related to the thaizine class of heterocyclic compounds. Derivatives of the parent compound find wide use as drugs. Application of microwave power system in the chemical synthesis of some phenothiazine derivatives is described. Heterocyclic ring formation, aromatic nucleophilic substitution and heterocyclic aldehydes or ketones condensation reactions were performed on solid support or under solvent free reaction conditions. Comparision of microwave assisted synthesis with the conventional synthetic methods demonstrates advantages related to shorter reaction times and in some cases better reaction yields. Structural elucidation of synthesized compounds has been made on the basis of elemental analysis, I.R. spectral studies and HNMR spectral studies. The antibacterial activity of these compounds have also been screened and found to be effective against gram + ve- and gram –ve bacteria


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