Synthesis of a potential angiogenesis inhibitor compound: 2-benzylidene cyclohexane-1,3-dione

Istyastono, Enade Perdana (Pharmaceutical Chemistry Lab., Faculty of Pharmacy, Sanata Dharma University, Paingan, Maguwohardjo, Yogyakarta)
Yuniarti, Nunung (Department of Pharmacology and Clinical Pharmacy, Faculty of Pharmacy Universitas Gadjah Mada Yogyakarta)
., Jumina (Department of Chemistry, Faculty of Mathematics and Natural Sciences Universitas Gadjah Mada Yogyakarta)

INDONESIAN JOURNAL OF PHARMACY
Vol 20 No 1, 2009

Synthesis of an aromatic cyclic enadione, 2-benzylidene-cyclohexane-1,3-dione (a potential angiogenesis inhibitor), has been done using benzaldehide (50 mmole) and cyclohexane-1,3-dione (50 mmole) as starting materials and NaOH 1.0 N as a catalyst. Odorless and white needle-shape powder has been achieved. The powder was 252.7 mg (2.53 %) and the purity of the powder was 88.81 %. Its melting point was 214.8 oC. The purity of the product was examined by gas chromatography, while the structure elucidation was done using IR spectrometer, 1H-NMR spectrometer, and GC-MS.IR spectrometer showed that the compound had a -C=O bond conjugated to an alkene or a phenyl moiety, methylen groups, and alkene’s -C–H bonds. 1H-NMR spectrometer showed that the compound had benzene moiety and methylen moieties, which were in α and β position to a carbonyl group. GC-MS showed that the molecular weight of the compound was 200 atomic mass unit.Key words: Angiogenesis inhibitor, synthesis, 2-benzylidene-cyclohexane-1,3-dione.