Synthesis of diacetyl gamavuton-0 using acetyl chloride as an acylating agent

Supardjan Amir Margono, Ridho Nugroho Zendrato

Abstract


Gamavuton-0 (GVT-0) is a curcumin-like compound, which is more stable than curcumin and still has an antioxidant property. The synthesis of diacetyl gamavuton-0 (diAcGVT-0) yielding an acetylation product that is more lipophile than GVT-0. The synthesis of diAcGVT-0 has been done by reacting GVT-0 and acetyl chloride as an acylating agent and tertiary amines as primary bases. DiAcGVT-0 was formed as the major product of synthesis but the product was not pure. Structure elucidation using UV-Vis, IR, 1H NMR and MS spectra showed that the main product was diAcGVT-0.

Key words : diacetyl gamavuton-0, acetyl chloride, acylating agent, lipophile


Full Text:

pdf 25-31

References


Anonim, 2004, Synthesis of Aspirin-Acylation of A Phenol Using Acetic Anhydride, http:// www.organic.wsu.edu/chem240/Ronald/labs/Aspirin/ Synthesis%20of%20Aspirin- Draft%204.pdf, 11 Oktober 2004.

Balasubramanyam, M., Koteswari, A.A., Kumar, R.S., Monickaraj, F., Maheswari, J.U., and Mohan, V., 2003, Curcumin-induced inhibition of cellular reactive oxygen species generation : Novel therapeutic implications, J. Biosci., 28, 6, 715-721.

Carey, F.A. and Sundberg, R.J., 2001, Advanced Organic Chemistry, Part B : Reaction and Synthesis, 4th Ed., Kluwer Academic/Plenum Publishers, New York, pp. 166.

Emafo, P., 2003, Speech on 46th Session of Commission on Narcotic Drugs, 8-17 April 2003.

Masuda, T., Jitoe, A., Isobe, J., Nakatani, N., and Yonemori, S., 1993, Anti-oxidative and Antiinflammatory Curcumin-related Phenolics from Rhizomes of Curcuma domestica, Phytochemistry, 32, 6, 1557-1560.

Meigawati, H.P., 2005, Sintesis Gamavuton-0 Dalam Pelarut Etil asetat Dengan Variasi Katalis Basa Organik, Skripsi, Fakultas Farmasi, UGM.

Nugroho, A.E., Supardjan, A.M., Hakim, L., Istyastono, E.P. and Yuniarti, N., 2004, Sintesis dan Uji Aktivitas Biologis Senyawa-senyawa Baru Turunan 1,5-bis(4′-hidroksi-3′-metoksifenil)-1,4-pentadien-3-on, Laporan Penelitian, Fakultas Farmasi Universitas Gadjah Mada, Jogjakarta.

Pedersen, U., Rasmussen, P.B., and Lawesson, S.-O., 1985, Synthesis of Naturally Occuring Curcuminoids and Related Compounds, Liebigs Ann. Chem., 1557-1569.

Roughley, P.J. and Whiting, D.A., 1973, Experiments in the Biosynthesis of Curcumin, J.C.S. Perkin I, 2379-2388.

Sardjiman, 2000, Synthesis of Some New Series of Curcumin Analogues, Antioxidative, Antiinflammatory, Antibacterial Activity, and Qualitative Structure Activity Relationship, Dissertation, Gadjah Mada University, Jogjakarta.

Sardjiman, S.S., Reksohadiprodjo, M.S., Hakim, L., van der Goot, H., and Timmerman, H., 1997, 1,5-Diphenyl-1,4-pentadiene-3-ones and cyclic analogues as antioxidative agents. Synthesis and structure-activity relationship., Eur. J. Med. Chem., 32, 625-630.

Youssef, K.M. and El-Sherbeny, M.A., 2005, Synthesis and Antitumor Activity of Some Curcumin Analogs, Arch. Pharm. Chem. Life Sci., 338, 181-189.




DOI: http://dx.doi.org/10.14499/indonesianjpharm0iss0pp25-31

Refbacks

  • There are currently no refbacks.




Copyright (c) 2017 INDONESIAN JOURNAL OF PHARMACY

Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Indonesian J Pharm indexed by:

web
analytics View My Stats