ANITA PUSPA WIDIYANA, 051514153016 (2017) SINTESIS SENYAWA-SENYAWA 3-(BENZILIDENAMINO)-2-(2,4-DIKLOROFENIL)KUINAZOLIN-4(3H)-ON DAN UJI AKTIVITAS ANTIKANKER PADA SEL KANKER PAYUDARA T47D. Thesis thesis, Universitas Airlangga.

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Abstract

The aim of the research were to obtain of 3-(benzylideneamino)-2-(2,4- dichlorophenyl)quinazolin-4(3H)-one derivatives and anticancer activity in breast cancer test on T47D cell. The compounds are synthesized by three reaction stages. The first stage, 2-aminobenzoic acid was reacted with 2,4-dichlorobenzoyl chloride to obtaining 2-(2,4-dichlorophenyl)-4H-benzo[1,3]oxazin-4-one. The second stage, 2-(2,4- dichlorophenyl)-4H-benzo[1,3]oxazin-4-one was reacted with hydrazine to obtaining 3-amino-2-(2,4-dichlorophenyl)quinazolin-4(3H)-one. The third stage, 3-amino-2-(2,4-dichlorophenyl)quinazolin-4(3H)-one was reacted with benzaldehyde and derivatives such as 4-methoxybenzaldehyde, 4-dimethylaminobenzaldehyde and 4-nitrobenzaldehyde. The melting point and TLC checks showed that the compounds are pure and continued for the structural confirmation test. The results of the confirmation structure of the compounds by the IR spectra, 1HNMR, 13CNMR and MS exhibited the compounds and can be synthesized from the starting material of 2-aminobenzoic acid with the percentage of yield between 45-53 %. The addition of substituents to the benzaldehyde group affects the length of reaction time. The duration of reaction time is -N (CH3)2 > -H > -OCH3 > -NO2. The 3-(benzylideneamino)-2-(2,4-dichlorophenyl)quinazolin-4(3H)-on compounds were tested for anticancer activity by MTT method on T47D cells. The four compounds have weaker anticancer activity than Celecoxib and predicted to qualitatively inhibit the cyclooxygenase-2 (COX-2) enzyme. The addition of dimethylamino substituents does not affect anticancer activity, whereas the addition of nitro substituents will decrease anticancer activity in T47D breast cancer cells.

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