ABSTRAK
Resistensi yang terjadi pada trimetoprim dan beberapa antibiotika konvensionallainnya menyebabkan pencarian akan molekul antibakteri baru dari golongansenyawa yang berbeda sangat dibutuhkan. Senyawa turunan kuinazolinondiketahui memiliki aktivitas antibakteri, oleh karena itu sintesis senyawa 6-amino-2-[(E)-(4-hidroksi-3-metoksifenil)etenil]-3,4-dihidrokuinazolin-4-on dan senyawaantaranya yang diujikan sebagai antibakteri perlu dilakukan. Senyawa 6-amino-2-[(E)-(4-hidroksi-3-metoksifenil)etenil]-3,4-dihidrokuinazolin-4-on disintesis denganempat tahap reaksi. Tahap pertama adalah sintesis 2-metil-3,4-dihidrokuinazolin-4-on, tahap kedua adalah sintesis 2-metil-6-nitro-3,4-dihidrokuinazolin-4-on, tahapketiga adalah sintesis 2-[(E)-(4-hidroksi-3-metoksifenil)etenil]-6-nitro-3,4-dihidrokuinazolin-4-on dan tahap keempat adalah sintesis 6-amino-2-[(E)-(4-hidroksi-3-metoksifenil)etenil]-3,4-dihidrokuinazolin-4-on. produk yang dihasilkandari setiap tahapan dimurnikan dengan cara pencucian dan rekristalisasi, kemudiandiuji kemurniannya dengan jarak lebur dan kromatografi lapis tipis. Bobot molekulsenyawa dianalsis dengan LC-MS, Struktur senyawa dielusidasi menggunakanspektrofotometri UV-Vis, FT-IR, 1H-NMR dan 13C-NMR, COSY, HMQC danHMBC. Uji aktivitas antibakteri dilakukan pada bakteri Staphylococcus aureusATCC 25923, Salmonella typhimurium ATCC 14028 dan Escherichia coli ATCC25922. Hasil penelitian menunjukkan bahwa senyawa target telah berhasil disintesisdan dimurnikan berdasarkan metode kimia organik. Struktur senyawa telahdibuktikan kebenarannya melalui elusidasi struktur. Hasil uji aktivitas antibakterisenyawa 6-amino-2-[(E)-(4-hidroksi-3-metoksifenil)etenil]-3,4-dihidrokuinazolin-4-on tidak menunjukkan aktivitas antibakteri.
ABSTRACT
Resistance in trimethoprim and several conventional antibacetria, made thesearching for new antibacterial agent from different groups of compound becamenescessary. Quinazolinone derivate was known having antibacterial activity, forthose reasons, synthesis of compound 6-Amino-2-[(E)-(4-hydroxy-3-methoxyphenyl)ethenyl)-6-nitro-3,4-dihydroquinazolin-4-one and its intermediateas antibacteria was necessary to be conducted. The titled compound wassynthesized via four steps. First step was synthesis of 2-methyl-3,4-dihydroquinazolin-4-one. Second step was syhtesis of 2-methyl-6-nitro-3,4-dihydroquinazolin-4-one. Third step was synthesis of 2-[(E)-(4-hydroxy-3-methoxyphenyl)ethenyl]-6-nitro-3,4-dihydroquinazolin-4-one. Forth step wassynthesis of 6-Amino-2-[(E)-(4-hydroxy-3-methoxy phenyl)ethenyl)-6-nitro-3,4-dihydroquinazolin-4-one. The synthesized product from each step was purified bywashing and recrystalization. The purity testing was performed by examiningmelting range and thin layer chromatography. Mollecuar mass of synthezisedcompound was determined using LC-MS. Structure of synthesized compound waselucidated using UV-Vis, FT-IR, 1H-NMR dan 13C-NMR, COSY, HMQC andHMBC. Screening for antibacterial activity was performed against Staphylococcusaureus ATCC 25923, Salmonella typhimurium ATCC 14028 and Escherichia coliATCC 25922. The result indicated that titled compound has sucsessfully beensynthesized and purified using organic chemistry method. Structure of desiredcompound was confirmed based on structural elucidation analysis. The result ofantibacterial activity of compound 6-Amino-2-[(E)-(4-hydroxy-3-methoxyphenyl)ethenyl)-6-nitro-3,4-dihydroquina-zolin-4-one did not perform antibacterialacitivity. |
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