SINTESIS DAN UJI AKTIVITAS ANTIBAKTERI SENYAWA N-ASETIL-PIRAZOLINA DARI p-ANISALDEHIDA DAN 4-HIDROKSIASETOFENON; SYNTHESIS AND ANTIBACTERIALTEST OF N-ACETYL-PYRAZOLINE FROM p-ANISALDEHYDE AND 4-HYDROXYACETOPHENONE

ISNAINI YULIANTI CHASYANAH, Deni Pranowo

2015 | Skripsi | FMIPA

Synthesis and antibacterialtest ofN-acetyl-pyrazoline have been carried out. Theaim of this research is to synthesis N-acetyl-pyrazolinefrom panisaldehyde and 4-hydroxyacetophenone and also to know its antibacterial activities. This research was begins by synthesis of 1-(4-hydroxy-phenyl)-3-(4- methoxy-phenyl)-2-propene (chalcone 1) via Claisen Schmidt condensation reaction between p-anisaldehyde and 4-hydroxyacetophenone using NaOH 40% as catalyst under stirring for 48 hours at room temperature. The next step was conducted by chalcone cyclization using hydrazine hydrate and glacial acetic acid to produce 3-(4-hydroxy-phenyl)-5-(4-methoxy-phenyl)-1-acetyl-2-pyrazoline (pyrazoline 1). The synthesis was conducted under reflux method for 26 hours. The product was analyzed using FT-IR, GC-MS, 1H- dan 13C-NMR spectrometer. Antibacterial test of pyrazoline compound was conducted by agar well diffusion method against Gram positive bacteria (Staphylococcus aureus, Bacillus cereus and Bacillus subtilis) and Gram negative bacteria (Escherichia coli and Shigella flexneri). The result showed that chalcone1 product was obtained as yellow crystal with melting point at 94.1-96.9?C and 88.19% yield. Then the cyclizationof chalcone produce pyrazoline 1as colorless crystal with melting point at 215.7- 216.9 ?C in 64.52% yield. Antibacterial test show that pyrazoline 1 was active against selectedGram positive bacteria i.e. S. aureus (4.5/300 dan 4.5/500), B. cereus (6.5/300), B. subtilis (3.25/500 dan 3.5/1000) and Gram negative bacteria i.e. E. coli (5.25/1000). Pirazoline 1 was not active against Gram negative bacteria S. flexneri.

Kata Kunci : Chalcone; Pyrazoline; p-Anisaldehyde; Antibacterial activity