Sylvone, a new furanoid lignan of

Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

“…Under such circumstances it is not easy to design inhibitors of sucient selectivity to target individual CYP isoforms because of several forms of CYP and wide range of overlapping substrates speci®cty. However, after introducing structural alterations in piperine a number of compounds synthesised exhibited preferential selectivity either towards constitutive or inducible CYPs (25,29,30). These compounds relatively exhibited maximal selectivity and higher CYP inactivating potency than the parent molecule as evidenced by their eect on microsomal MOCD activities.…”

“…The resulting precipitate ®ltered, washed with ice cold water and dried to give acid (4a) (6.7 g, 82%) crystallised from ethyl acetate:petroleum ether (9:1) as colourless compound, mp 183 C (lit. mp 182±183 C), 23,25,26 analysed Scheme 2. , 1688, 1668, 1612, 1550, 1440, 1320, 1040, 960 Preparation of 5-(4-methoxy phenyl)-2E,4E-pentadienoic acid piperidine amide (8).…”

Cyclobutanoid Amides from Piper arborescens

“…The 1 H-NMR data of 1 were very similar to that of piplartine-dimer A (4) [5], also isolated in this study, except for the presence of the ABX pattern at d 6.77 (d, J 8.4 Hz, 2 H, HÀC(14,14')), 6.82 (d, J 2.0 Hz, 2 H, HÀC(11,11')), and 6.89 (dd, J 8.4, 2.0 Hz, 2 H, HÀC(15,15')) for the substituted phenyl groups of 1 in place of the s at d 6.51 (4 H) for the aromatic protons of 4, and except for 2s at d 3.84 and 3.86 (each 6 H) for MeOÀC(12,12') and MeOÀC(13,13') 1 ), respectively, in 1. Four cyclobutane protons were determined by HMBC; the signal at d 4.75 (dd, J 11.2, 8.0 Hz, 2 H) was assigned to HÀC(9,9') due to its 3 J correlation with d 112.1 (C(11,11')) and 120.0 (C(15,15')) and the signals at d 6.82 (HÀC(11,11')) and 6.89 (HÀC(15,15')) showing 3 J correlation with d 41.6 (C(9,9')).…”

Enantioselective Synthesis of a Furan Lignan (+)-Sylvone

“…5 +9.6°). 5,7 In summary, this paper describes a facile enantioselective synthesis of sylvone (1) from methyl allenoate involving the use of several key transformations to construct a 2,3,4-trisubstituted sylvone skeleton with the appropriate three contiguous stereogenic centers: α-addition of an aldehyde of an allenoate, oxacyclization of 2 to 3, and diastereoselective conjugate addition of a 1,3-dithiane derivative to 3. This synthetic route may prove to be a general and efficient method for synthesis of related furan lignan natural products and their analogues.…”

“…The organic layers were washed with brine (1×), dried over Na 2 SO 4 , filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/ ethyl acetate = 4:1) to afford sylvone 1 (65 mg, 0.15 mol, 75%) as a pale yellow solid: 5,7 9, 49.8, 56.0, 56.0, 56.4, 61.0, 62.1, 69.2, 81.5, 106.3, 108.8, 111.2, 117.8, 130.5, 131.4, 142.9, 148.3, 149.0, 153.2, 198.6; MS (ESI) m/z 433.2 (M+1).…”