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Modifikasi gugus fungsi pada senyawa 4-aminofenol akan menyebabkan perubahan sifat fisika kimia senyawa, yang diharapkan dapat meningkatkan respon biologis. Parasetamol yang berkhasiat analgesik dan antipiretik merupakan salah satu senyawa hasil modifikasi 4-aminofenol. Abdul-Hussein (2014) melakukan penelitian terkait efek antibakteri dari parasetamol. Penelitian tersebut menunjukkan bahwa parasetamol memiliki efek antibakteri terhadap E.coli, S.aureus, K.pneumonia, dan P.aeruginosa seiring dengan kenaikan konsentrasi.Pada penelitian ini, dilakukan optimasi sintesis turunan 4-aminofenol lainnya yakni N,O-dibenzoil p-aminofenol. Senyawa analgetika yang berhasil disintesis pada penelitian sebelumnya ini dapat diperoleh dari reaksi antara 4-aminofenol dan benzoil klorida, dengan rendemen sebesar 10,69%.
Faktor optimasi meliputi urutan pencampuran starting material, jenis pelarut, volume pelarut, penambahan katalis, dan perbandingan mol starting material. Penelitian dilanjutkan dengan uji eksploratif aktivitas antibakterinya sehingga dapat memberikan tambahan informasi efek antibakteri dari senyawa N,O-dibenzoil p-aminofenol. Uji aktivitas antibakteri dilakukan menggunakan metode mikrodilusi terhadap 4 spesies bakteri, yakni Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, dan Klebsiella pneumoniae, dengan parameter akhir yang dianalisis adalah nilai KHM50.Optimasi sintesis N,O-dibenzoil p-aminofenol menghasilkan rendemen akhir 62,94%. Produk yang dihasilkan terkonfirmasi sebagai senyawa target dibuktikan dengan analisis KLT, reagen warna, titik lebur, dan spektrofotometri IR.
Uji antibakteri menunjukkan nilai KHM50 senyawa N,O-dibenzoil p-aminofenol terhadap S.aureus sebesar 5,36 mg/mL; terhadap E.coli sebesar 8,18 mg/mL; terhadap P.aeruginosa sebesar 5,68 mg/mL; dan terhadap K.pneumonia sebesar 5,22 mg/mL.Functional group modification of 4-aminophenol will lead to any alterations of physical and chemical properties, thus hopefully can improve biologic response. Paracetamol, popularly known as analgesic and antipyretic drug, is one of the 4-aminophenol modified compounds.
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Abdul-Hussein (2014) did a research related to the antibacterial effect of paracetamol. The study showed that paracetamol inhibit the growth of E.coli, S.aureus, K.pneumonia, and P.aeruginosa with increasing of the concentration of the drug.In this research, another 4-aminophenol modified compound had been synthesis-optimized, that was N,O-dibenzoyl p-aminophenol. This analgesic compound which have been successfully synthesized in a previous study, could be obtained from the reaction between 4-aminophenol and benzoyl chloride, provided yield of 10,69%. Optimization factors include the sequence of mixing of starting material, solvent type, solvent volume, catalyst addition, and starting material mol ratio.
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Research was continued with an explorative test of its antibacterial activity, so that it can provide additional information about the antibacterial effect of N,O-dibenzoyl p-aminophenol. The antibacterial activity test was performed using microdilution method on 4 species of bacteria (Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Klebsiella pneumoniae). The final analyzed parameter was the value of MIC50.Optimization of the synthesis of N,O-dibenzoyl p-aminophenol obtained a final yield of 62.94%.
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The resulting product was confirmed as the target compound as evidenced by TLC analysis, color reagent, melting point, and IR spectrophotometry. Antibacterial test showed MIC50 value of N,O-dibenzoyl p-aminophenol against S.aureus of 5.36 mg/mL; against E.coli of 8,18 mg/mL; against P.aeruginosa of 5,68 mg/mL; and against K.pneumonia of 5,22 mg/mL.Kata Kunci: N,O-dibenzoil p-aminofenol, optimasi sintesis, antibakteri.