Synthesis of Tetrahydrohexagamavunon-5 and Tetrahydrohexagamavunon-7

Abstract

Synthesis of Tetrahydrohexagamavunon-5 (THHGV-5) and Tetrahydrohexagamavunone-7 (THHGV-7) were prepared by catalytic hydrogenation reaction on Hexagamavunon-5 (HGV-5) and Hexagamavunone-7 (HGV-7) by using gas H 2 as source of hydrogen gas, Pd/C 10 % as metal catalyst and methanol as solvent at room temperature. According to previous study, Pd/C catalyst is more specific than other metal catalyst to reduce α,β-unsaturated double bond without reduction of its carbonyl functional group.

Preparation and Cytotoxic Evaluation of PGV-1 Derivative, CCA-1.1, as a New Curcumin Analog with Improved-Physicochemical and Pharmacological Properties

“…Taken together, the structure of CCA-1.1 was successfully synthesized through PGV-1 reduction, and the result was confirmed basing from on its functional group through IR spectroscopy. The 1 H-NMR (Supplementary Figure 2) and 13 C-NMR (Supplementary Figure 3) spectra showed five and eight resonance peaks, respectively, confirming that CCA-1.1 is a symmetrical molecule similar to PGV-1 and curcumin. The very downfield broad signal at  8.84 in the 1 H-NMR spectrum was characteristic for aromatic hydroxyl proton.…”

“…The reagents and solvents in this experiment were classified as an analytical grade unless otherwise stated. The 1 H-and 13 C-NMR spectra of CCA-1.1 were recorded in DMSO-D6 with a JNM-ECZ500R (500 MHz, JEOL Ltd., Tokyo, Japan) spectrometer. FT-IR spectrum (KBr disc) was determined using an FT-IR spectrophotometer (Perkin Elmer, USA) at 4000-400 cm -1 .…”

“…The rest singlet signal at  2.20 ppm was referred to two methyl protons attached to the benzene ring at positions 3' and 5'. In the 13…”

“…We are considering the ,-diene system in the structure of PGV-1, a selective agent that can reduce only the carbonyl ketone group must be used. For this reaction, NaBH4 can be chosen instead of H2 gas with a palladium catalyst 13 . NaBH4 reagent is a chemo-selective reducing agent and often be used to reduce carbonyl to the hydroxy group, which is carried out under appropriate conditions 14 15 .…”