SYNTHESIS AND PHYSICOCHEMISTRY PROPERTIES PREDICTION OF A NEW POTENTIAL ANTI-INFLAMMATORY AGENT: DIACETYL PENTAGAMAVUNON-1

https://doi.org/10.22146/ijc.21782

Supardjan A. Margono(1*), Pudjono Pudjono(2), St. Layli Prasojo(3), Jeffry Julianus(4), Enade Perdana Istyastono(5)

(1) Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada, Sekip Utara Yogyakarta 55281
(2) Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada, Sekip Utara Yogyakarta 55281
(3) Centre for Education and Research ENADION - Yogyakarta
(4) Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Universitas Gadjah Mada, Sekip Utara Yogyakarta 55281
(5) Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Sanata Dharma, Paingan, Maguwoharjo Yogyakarta 55281
(*) Corresponding Author

Abstract


Synthesis and physicochemistry properties prediction of a potential anti-inflammatory agent, diacetyl pentagamavunon-1 (diacetyl PGV-1), has been done. The synthesis was using pentagamavunon-1 (PGV-1) (2,87x10-3 mole) and anhydride acetic acid (26x10-3 mole; 37x10-3 mole; 49x10-3 mole) as starting materials and NaOH ethanolic as a catalyst. The AM1 semiempirical quantum-chemical calculations using the computational chemistry approach was used to predict and compare the physicochemisty properties of diacetyl PGV-1 to PGV-1. Odorless, light-yellow powder has been obtained. The powder was 0.8512-0.9602 g (2.02 x10-3 - 2.22x10-3 mole; 70.4-77.4%) and the purity of the powder was 92.4%. The purity of the product has been examined by high performance liquid chromatography (HPLC), while the structure elucidation has been done using IR (Infra Red), 1H-NMR (Nuclear Magnetic Resonance) and MS (Mass Spectroscopy). The physicochemisty properties prediction showed that diacetyl PGV-1 was more hydrophobic than PGV-1.


Keywords


Anti-inflammatory; PGV-1; diacetyl PGV-1; AM1

Full Text:

Full Text Pdf


References

[1]   Kalgutkar, A.S., Crews, B.C., Rowlinson, S.W., Garner, C., Seibert, K, Marnett, L.J., 1998, Science, 280, 1268-1270.

[2]   Hamor, G.H., 1989, Nonsteroidal Anti-inflammatory Drugs, in Principle of Medicinal Chemistry, Edited by: W.O. Foye, Lea & Febiger, Piladelphia, 503-530.

[3]   Vane, J.R., and Botting, R.M., 1996, Overview-Mechanism of Action of Anti-inflammatory Drugs in Improved Non-Steroid Anti-Inflammatory Drugs COX-2 Enzyme Inhibitors, Eds. Vane, S.J., Botting, J., and Botting, R., Kluwer Academic Publishers and William Harvey Press, Great Britain, 1-28.

[4]   Van Bladeren, P.J. and Van Ommen, B., 1991, Pharmacol. Ther., 51, 35-46.

[5]   Sardjiman, 2000, Synthesis of some new series of curcumin analogues, anti-oxidative, anti-inflammatory, antibacterial activities and qualitative structure-activity relationship, PhD Thesis, Gadjah Mada University, Yogyakarta.

[6]   Istyastono, E.P., Sudibyo, M., Pranowo, H.D., dan Tahir, I., 2003, Indo. J. Chem., 3 (3), 179-185.

[7]   Istyastono, E.P. dan Sudibyo, M., 2005, Majalah Farmasi Indonesia, 16 (4), 204-213.

[8]   Sudarmanto, B.S.A., 2002, Analisis Hubungan Kuantitatif Struktur-Aktivitas Seri Senyawa Analog Kurkumin Sebagai Antioksidan Menggunakan Deskriptor Berdasarkan Perhitungan Kimia Kuantum, Tesis S2, Fakultas MIPA, Universitas Gadjah Mada, Yogyakarta.

[9]   Wang, J., Niemevs, F., Lad, L., Huang, L., Alvares, D.E., Buldain, G., Poulos, T.L., and de Montellano, P.R.O., 2004, J. Biol. Chem, 279 (41), 42593-42604.

[10] Nakano, T., Kaminuma, T., Uebayasi, M., and Nakata, Y., 2001, Chem-Bio Inform. J., 1 (1), 35-40.

[11] Silverstein, R.M. and Webster, F.X., 1998, Spectrometric Identification of Organic Compounds, 6th edition, John Wiley & Sons, Inc, Canada.

[12] Nurfina, A.N., Reksohadiprojo, M.S., Timmerman, H., Jenie, U.A., Sugiyanto, D., and Van der Goot, H., 1997, Eur. J. Med. Chem., 32, 321-328.

[13] Supardjan, A. M., 1999, Synthesis and Anti-inflammatory Activity of Some 4-substitued Curcumin Derivatives, PhD Thesis, Gadjah Mada University, Yogyakarta.

[14] Istyastono, E.P., Supardjan, A.M., dan Pranowo, H.D., 2003, Majalah Farmasi Indonesia, 14 (3), 107-113.

[15] Septika, E., 2005, Uji Efek Analgetik Diasetil Pentagamavunon-1 pada Mencit Jantan Galur BALB/C dengan Metode Rangsang Kimia, Skripsi, Fakultas Farmasi, Universitas Gadjah Mada, Yogyakarta.



DOI: https://doi.org/10.22146/ijc.21782

Article Metrics

Abstract views : 460 | views : 1247


Copyright (c) 2010 Indonesian Journal of Chemistry

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

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.