Synthesis and Study the Antioxidant Activity of some new Heterocyclic Compounds from chalcone

This work involves the synthesis of different five, six and seven membered heterocyclic rings starting from different chalcone derivatives. This work is divided into five different parts:
First part (Scheme 1, 2):A- This part involves the synthesis of new derivatives of α, β-unsaturated ketones (chalcones) using Claisen Schmidt condensation reaction of different aromatic ketones with different aromatic aldehydes to produce (1, 3-diaryl-2-propen-1-one) [A1 (a-g)]. (Scheme 1)B- The synthesized chalcones [A1 (a-g)] were used as starting materials to synthesize another kind of heterocyclic compounds including five, six and seven membered heterocyclic rings. These new compounds are 2-amino[4-(1-naphthyl)-6(2-naphthyl)]pyrimidine [A2(a-c)],pyrazolines [A5(a-d)],ethyl6-(naphthalen-1-yl)4-(naphthalen-2-yl)-2-oxocyclohex-3-enecarboxylate [A8], [4-(1-naphthyl)-6-(2naphthyl)-2-oxo]pyrimidine [A10], [4-(1-naphthyl)-6-(2-naphthyl)-2thione]pyrimidine [A11], [1-carbothioamidyl-3-(1-naphthyl)-5-(2-naphthyl)]-2pyrazoline [A12], by reacting of one mole of chalcones [A1] with one moles of guanidine hydrochloride, hydrazine hydrate, ethyl aceto acetate, urea, thiourea and thiosemicarbazide respectively (Scheme 2).  C- Some of these synthesized compounds in part (B) were used to synthesize other kinds of heterocyclic compounds derivatives include methyl 5-(naphthalen-1-yl)-3(naphthalen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboxylate [A6]and 5-(naphthalen-1yl)-3-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbohydrazide [A7], were synthesized from the reaction of pyrazoline derivative with methyl chloro formate to give compound [A6]. and with hydrazine hydrate to give compound [A7] (Scheme2).D- Also this part involves, the reaction of compound [A8] with hydrazine hydrate,2,4-dinitrophenylhydrazine and 2-aminobenzothiazole to produce compounds [A9(a,b,c)]  (Scheme 2).Second part (Scheme 3):A- This part includes the synthesis of different derivatives of Schiff bases [A3 (a,b)],by the reaction of 2-amino-4,6-Arylpyrimidine [A2 (a-c)] with 2hydroxybenzaldehyde,naphthaldehyde, benzaldehyde, 4-nitrobenzaldehyde,furfural, 4-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, 3-bromobenzaldehyde,4-bromobenzaldehyde and  2-hydroxynaphthaldehyde respectively (Scheme 3).B- This part also includes the synthesis of amide derivatives, by the reaction of 4-(2amino-6-phenylpyrimidin-4-yl)phenol [A2c] with different esters such as ethyl acetate, ethyl chloroformate, ethyl aceto acetate, n-butyl acetate and Di-n-butyl phthalate to produce the compounds [A4(a,b,c,d,e)] (Scheme 3).Third part (Scheme 4):This part includes the synthesis of dihydroquinazoline [A16a], imidazolidine4-one [A16b], oxazepine [A16c], Tetrazoline [A16d] and thiazolidine-4-one [A16e] derivatives derived from the cyclization of Schiff base [A15] which synthesized from 1-naphthaldehyde and 4-aminoantipyrine, then the Schiff base was treatment with 2-amino benzoic acid (anthranilic acid), glycine, phthalic anhydride, sodium azide and 2-mercapto acetic acid respectively (Scheme 4).Fourth part:All the synthesized compounds are determined their physical properties (melting points, colors), (FT-IR) spectroscopy and some of them by (H-NMR)spectroscopy and (CHNS) analysis.Fifth part:The free radical scavenging activities were studied using stable free radical compound 1,1-Diphenyl-2-Picryl-hydrazil (DPPH•) for some of synthesized compounds [A1b, A2b, A3e, A3h, A4a, A5a, A6, A7, A8, A9c, A12, A15, A16b]. The Results  showed  that these compounds has varying activity for the free radical scavenging in different concentrations  (12.5, 25, 50 and 100) µg/ml (80.63%, 27%,37%, 61%, 50.62%, 45.83%, 69%, 75.63%, 38.65%, 56.54%, 41.75%, 23.90%,58%) respectively in 100 µg/ml compared with vitamin C (ascorbic acid), which shows the effectiveness of the scavenging free radicals by 80% at a concentration of 100 µg/ml.