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Dwi Siswanta
Chemistry Department , Faculty Of Mathematics And Natural Science, Gajah Mada University, Sekip Utara, Yogyakarta, Indonesia
Agriculture, Biological Sciences & Forestry Astronomy Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Control & Systems Engineering Earth & Planetary Sciences Education Energy Engineering Environmental Science Immunology & microbiology Industrial & Manufacturing Engineering Materials Science & Nanotechnology Mathematics Medicine & Pharmacology Neuroscience Physics Social Sciences

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Journal : INDONESIAN JOURNAL OF PHARMACY

 1 
SYNTHESIS AND BIOLOGICAL ACTIVITY EVALUATION OF C-9154 ANTIBIOTIC DERIVATIVES FROM VANILLIN ., Jumina; Siswanta, Dwi; Zulkarnain, Abdul Karim
Indonesian Journal of Pharmacy Vol 12 No 2, 2001
Publisher : Faculty of Pharmacy Universitas Gadjah Mada, Yogyakarta, Skip Utara, 55281, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (68.404 KB) | DOI: 10.14499/indonesianjpharm0iss0pp85-91

Abstract

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.
Co-Authors ., Jumina Abdul Karim Zulkarnain Abner Tonu Lema Adhitasari Suratman Adhitasari Suratman Adhitasari Suratman Adhitasari Suratman Agnes Dyah Novitasari Lestari Agung Abadi Kiswandono Ahmad Nasir Pulungan Akhmad Damsyik Aloisius M. Kopon Aloisius Masan Kopon Anjar Purba Asmara Anselmus Boy Baunsele Arifina Febriasari Bambang Kuswandi Bambang Kuswandi Bambang Rusdiarso Bambang Rusdiarso Desi Suci Handayani Dhony Hermanto Eko Sugiharto Eko Sugiharto Eni Kartika Sari Erly Grizca Boelan Faderina Komisia Febi Indah Fajarwati Fidelis Nitti Fitriana, Dina Fitrilia Silvianti Girsang, Ermi Herdiansyah Herdiansyah Herdiansyah Herdiansyah Hidetaka Kawakita Hildegardis Missa Jumina Jumina Jumina Jumina Jumina Jumina Juniva Laila Sihombing, Juniva Laila Karelius Karelius Keisuke Ohto Kopon, Aloisius Masan Leba, Maria A. U. M. Cholid Djunaidi Maria A. U. Leba Maria Aloisia Uron Leba Maria Benedikta Tukan Merpiseldin Nitsae Mudasir Mudasir Mudasir Mudasir Mudasir Mudasir Mudasir Mudasir Mustofa Mustofa Naat, Johnson N. Neolaka, Yantus A B Ni Putu Sri Ayuni Nindita Clourisa Amaris Susanto Nugraha, Gerry Nurillahi Febria Leswana Nurul Hidayat Aprilita Nurul Ismillayli Pratama J. Wibawa Rahayu Rahayu Rahayu Rahayu Rahayu Rahmat Basuki Rahmat Basuki Retno Ariadi Lusiana Rika Wulandari Rika Wulandari Romelos Untailawan Sehol, Muhamad Soerja Koesnarpadi Sri Juari Santosa Sri Juari Santosa Sri Juari Santosa Suyanta Suyanta Taek, Maximus M. Takashi Hayashita Triana Kusumaningsih Tukan, Gerardus D. Uripto Trisno Santoso Widya Krestina, Luqman Hakim, Dyah Ayu Pramoda Wardani,