Synthesis and Characterization of Some Substituted Flavonoids and its Associated Pharmacological Activity

Abstract

The present study was carried out to synthesize and to screen the newly developed compound for its pharmacological activity. First attempt of the study was to synthesized the substituted 3-hydroxy flavones derivative by the Algar-Flynn- Oyamada reaction between acetophenone derivative like 2-hydroxy acetophenone, 2- hydroxy p-methoxy acetophenone, 2- hydroxyl 5- methyl-2-hydroxy acetophenone and various aldehyde such as p-dimethyl amino benzaldehyde, p-dimethyl aminobenzaldehyde, p-chlorobenzaldehyde, furfuraldehyde, to give chalcone product which further condense in presence of hydrogen peroxide and ethanol to yield the desired flavonol derivative. Both analytical and spectral data (IR,1H and 13C-NMR) of all the synthesized compound were in full agreement with the synthesized structure. The monitoring of the reaction and purity of the obtained compound were checked by TLC. The purification of crude product as well as separation of formed isomer was done by applying recrystallisaion. The structure elucidation of newly obtained molecule and compound formed according to the literature was proved primary on the base of NMR measurement. Additionally, elemental analysis data, IR, Mass were also used. The NMR measurement was executed on the samples dissolved in different denatured solvent. Compound belonging to all the major flavones were studied. On the bases of order of pharmacological studies of test compound the following structure activity relationship (SAR) was observed. 1. At C-2, p-dimethylamino phenyl, p-chlorophenyl substitution showed the best activity followed by furyl substitution. 2. Non substitution by flavone ring at C-7 and 6 was less favourable for the activity then C-7 methoxy and C-6 methyl sustitutiuon. 3. At C-4 substitution of C-2 phenyl Ring was more favorable C-4 substitution of C-2 phenyl ring and furyl substitution. However, further experiments will possibly define this pharmacological effect and associated mechanism. It may become of importance for human clinical treatments. newline