SYNTHESIS AND BIOLOGICAL ACTIVITY EVALUATION OF C-9154 ANTIBIOTIC DERIVATIVES FROM VANILLIN
| Main Authors: | ., Jumina; Chemical Organic Laboratory Departement of Chemistry Faculty of Science and Mathematic Universitas Gadjah Mada Yogyakarta, Siswanta, Dwi; Analitical Chemical Laboratory Departement of Chemistry Faculty of Science and Mathematic Universitas Gadjah Mada Yogyakarta, Zulkarnain, Abdul Karim; Pharmaceutical Laboratory Faculty of Pharmacy Universitas Gadjah Mada Yogyakarta |
|---|---|
| Format: | Article info eJournal |
| Bahasa: | eng |
| Terbitan: |
Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Skip Utara, 55281, Indonesia
, 2005
|
| Online Access: |
http://indonesianjpharm.farmasi.ugm.ac.id/index.php/3/article/view/532 http://indonesianjpharm.farmasi.ugm.ac.id/index.php/3/article/view/532/410 |
Daftar Isi:
- This research was conducted in order to synthesize two derivatives of C-9154 antibiotic from vanillin and to evaluate their biological activities. The synthesis of these C-9154 derivatives was performed through alkylation of vanillin, preparation of the corresponding benzaldoxim, reduction of this benzaldoxim, treatment of the resulting substituted benzilamine with maleic anhydride and esterification of this C-9154 antibiotic derivative. The alkylation of vanillin was carried out using diethylsulfate and NaOH as the base to give 89% yield of ethyl vanillin. The oxim synthesis from ethyl vanillin was performed using hydroxylamine hydrochloride under alkaline condition at 50oC for 2 hours to yield 89% 4-ethoxy-3-methoxybenzaldoxim. Reduction of this benzaldoxim with metallic Na in absolute ethanol afforded 82% yield of 4-ethoxy-3-methoxybenzylamine. This benzylamine derivative was then reacted with maleic anhydride in benzene to give the acid-form of C-9154 antibiotic derivative (6) in 74% yield. Esterification of this acid conducted Jumina using absolute ethanol in the presence of concentrated sulfuric acid at reflux for 4 hours gave the ethyl ester-form of C-9154 antibiotic derivative (7) in 87% yield. Antimicrobial activity evaluation was conducted using Staphyllococcus aureus and Eschericia coli. Based on the minimum inhibition concentration (MIC) data determined using aqueous methanol as the reference, it was observed that the acid-form (6) and the ethyl ester-form (7) of C-9154 antibiotic derivative obtained respectively gave MIC values of 2000-3000 g/ml and 500-1000 g/ml respectively either towards Staphyllococcus aureus or Eschericia coli.Key words: antibiotics, vanillin, oxim, benzylamine, C-9154 derivative, antimicrobe.