6-Hydr­oxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexa­hydro­phenanthren-9(1H)-one

The title compound, C20H28O2, commonly named Sugiol, is a natural oxygenated diterpene that we have isolated for the first time from a hexane extract of the fruits of Juniperus Oxycedrus L. Its X-ray crystal structure determination confirms an abietane skeleton which was predicted by spectroscopic analysis, mainly by 1H and 13C NMR. The cyclo­hexane ring adopts a flattened chair conformation, while the cyclo­hexene ring adopts an envelope conformation. The mol­ecules are linked through O—H⋯O hydrogen bonds to form a zigzag chain extending parallel to the c axis

1,4a-Dimethyl-6-methyl­ene-5-(5,5,6,6-tetra­cyano-2-methyl­cyclo­hex-2-enylmeth­yl)deca­hydro­naphthalene-1-carboxylic acid: a trans-communic acid derivative

In the search for cancer chemopreventive agents, we have studied the Diels–Alder reaction of trans-communic acid with tetra­cyano­ethyl­ene in the presence of SiO2 as catalyst. The title cycloadduct, C26H30N4O2, was obtained in 75% yield. The mol­ecules are arranged in pairs through O—H⋯O hydrogen bonds, forming an R 2 2(8) ring motif. Both the fused cyclohexyl rings adopt a chair conformation, whereas the nonfused ring adopts a half-chair conformation

Click synthesis, anticancer activity, and molecular docking investigation of some functional 1,2,3-triazole derivatives

1,2,3-triazole skeleton is a privileged building block for the discovery of new promising anticancer agents. In this report, new 1,4-disubstituted 1,2,3-triazoles with the bioisoster triazole moiety were straightforwardly prepared under copper-catalyzed azide-alkyne [3+2] cycloaddition reactions (CuAAC) regime using a variety of both functional organic azides and terminal alkynes. The resulting functional 1,4-disubstituted 1,2,3-triazole compounds were fully characterized and subsequently tested for their antiproliferative activity against four different cancer cell lines. The cytotoxicity tests carried out with these 1,2,3-triazole derivatives show average IC50 values ranging from 15 to 50 μM by comparison with the standard reference drug, namely doxorubicin. The phosphonate 1,2,3-triazole derivative was found to exhibit the best antiproliferative activity among the studied compounds against the HT-1080 cell lines. It was chosen to evaluate its mode of action in these cancer cell lines. The cell cycle study showed that the phosphonate derivative, compound 8, is the most active inhibitor of the cell cycle at the G0/G1 phase, inducing apoptosis independently of Caspase-3 and causing an increase in the mitochondrial membrane potential (ΔΨm) in the HT-1080 cell lines. Molecular docking studies of this phosphonate derivative into the MMP-2 and MMP-9 metalloproteinases receptors demonstrated the relevance of triazole scaffolds and the pendant phosphonate group in establishing -anion, -alkyl and hydrogen bonding type interactions with residual components in the active MMP pocket

Crystal structure of (1R,3S,8R,11R)-11-acetyl-3,7,7-trimethyl-10-oxatricyclo[6.4.0.01,3]dodecan-9-one

International audienceThe title compound, C16H24O3, is built up from three fused rings, a six-membered, a seven-membered and a three-membered ring. The absolute configuration of the title compound was determined as (1R,3S,8R,11R) based on the synthetic pathway. The six-membered ring has an half-chair conformation whereas the seven-membered ring displays a boat conformation. In the cyrstal, C-H...O hydrogen bonds build up a two-dimensional network parallel to (0 0 1). The crystal studied was an inversion twin with a minor twin component of 34%

(1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

International audienceThe title compound, C16H22Br4, was synthesized in two steps from [beta]-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). It is built up from three fused rings, a seven-membered heptane ring, a six-membered cyclohexyl ring bearing both a bromine and a bromomethyl substituent, and a three-membered propane ring bearing two Br atoms. In the crystal, molecules are linked by C-H...Br hydrogen bonds, forming chains propagating along [001]. The absolute configuration was deduced from the chemical pathway and confirmed by resonant scattering [Flack parameter = 0.012 (10)]

(1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecane

The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-ene with metachloroperbenzoic acid. The molecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present

Absolute configuration of (1S,3R,8R)-10-bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven-membered ring is a twisted chair. The molecular packing within the crystal is stabilized only by van der Waals interactions

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate

The hemisynthesis of the title compound, C22H32O2, was carried out through direct acetylation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol]. The molecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [−0.10 (6)] allowed this absolute configuration to be confirmed

Crystal structure of (1R,2S,4R,7R,8S,9R)-3,3-dichloro-8,9-epoxy-4,8,12,12-tetramethyltricyclo[5.5.0.02,4]dodecane

International audienceThe title compound, C16H24Cl2O, is built up from two fused six- and seven-membered rings which bear a dichlorocyclopropane group and an epoxy group, respectively. In the molecule, the six-membered ring adopts an envelope configuration with the C atom linking the epoxy ring at the flap, while the seven-membered ring adopts a boat-sofa conformation