Zhanqian Song

Synthesis and antitumor activities of unsymmetrically disubstituted acylthioureas fused with hydrophenanthrene structure

A series of novel unsymmetrically disubstituted acylthioureas fused with hydrophenanthrene structure were synthesized from Δ8-dihydroabietic and dehydroabietic acid, respectively. Their structures were characterized by IR, 1H-, and 13C-NMR spectroscopy. The antitumor activities of the title compounds against SMMC7721 and A549 tumor cells were evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) method. The results showed that three compounds (4c1, 4d1, and 4d2) exhibited highly effective activities against SMMC7721 and A549 cells, their IC50 values are between 1.87–12.67xa0μM for SMMC7721 cells and 2.20–6.79xa0μM for A549 cells, respectively. Structure–activity relationship indicating that acylthioureas that furan group fused with Δ8-dihydroabietyl group, trihydroxymethyl fused with Δ8-dihydroabietyl and dehydroabietyl could generate enhance activities of this kind of compounds against SMMC7721 and A549 cells.

Highly Efficient One-Pot Synthesis of α-Aminophosphonates Catalyzed by Ytterbium Triflate in Water

Abstract A facile one-pot, three-component synthesis of α -aminophosphonates catalyzed by ytterbium triflate [Yb(OTf)3] in water using polyoxyethanyl α -tocopheryl sebacate (PTS) as amphiphile has been developed. The catalytic system could be readily recycled and reused several times without significant loss in its activity. GRAPHICAL ABSTRACT

Dehydro­abietic acid

The title compound [systematic name: (1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid], C20H28O2, has been isolated from disproportionated rosin which is obtained by isomerizing gum rosin with a Pd-C catalyst.. Two crystallographically independent molecules exist in the asymmetric unit. In each molecule, there are three six-membered rings, which adopt planar, half-chair and chair conformations. The two cyclohexane rings form a trans ring junction with the two methyl groups in axial positions. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds.

4-Chloro-2-{(E)-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa­hydro­phenanthren-1-yl]methyl­imino­meth­yl}phenol

The title compound, C27H34ClNO, was synthesized by a direct condensation reaction. The molxadecule has three chiral centres, which exhibit R, S and R absolute configurations, respectively. Two six-membered rings with different conformations coexist in the structure and they form a trans ring junction with two methyl groups in axial positions.

The green approaches for the synthesis of N -dehydroabietic α -aminophosphonates

Three kinds of O,O-diethyl N-dehydroabietic aminoarylmethylphosphonates were synthesized from natural product derivatives by two steps of solvent-free reactions through imines intermediates and their structures were characterized by IR, 1H NMR and 31P NMR spectroscopy. The solvent-free reactions afforded good yields of N-dehydroabietic imines and α-aminophosphonates although the strong space block of dehydroabietylamine to amino group. The green approaches resulted negligible waste and the reactions were environment friendly without using noxious solvents.

Methyl 12-bromo­dehydro­abietate

The title compound [systematic name: (1R)-methyl 6-bromo-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate], C21H29BrO2, was synthesized from N-bromosuccinimide and methyl dehydroabietate, which was prepared through an esterification reaction using dehydroabietic acid and methanol as raw materials. The three six-membered rings adopt planar (mean deviation = 0.002u2005Å) half-chair and chair conformations. The two cyclohexane rings form a trans ring junction with the two methyl groups in axial positions. The crystal structure is stabilized by weak intermolecular C—H⋯O contacts along the b axis.

7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodeca­hydro­phenan­threne-1-carboxylic acid

The title compound, C20H32O2, has been isolated from hydrogenated rosin. There are two independent molecules in the asymmetric unit. In each molecule, the cyclohexane ring assumes a chair conformation, while the two cyclohexene rings adopt half-chair and envelope conformations. Intermolecular O—H⋯O hydrogen bonding between carboxyl groups links pairs of independent molecules into dimers.

Synthesis and crystal structure of maleopimaric acid

The title compound maleopimaric acid was synthesized by a Diels–Alder reaction between maleic anhydride and Pinus elliottii engelm oleoresin at room temperature and it was characterized by single crystal X-ray diffraction. The white crystals crystallized in the orthorhombic system, space group P2 12121 with cell dimensions: a = 7.6960 (15) Å, b = 11.851 (2) Å, c = 24.577 (5) Å, α = 90°, β = 90°, γ = 90°, V = 2241.6(8) Å3, and R 1 = 0.0716, wR 2 = 0.1975. The two fused and unbridged cyclohexane rings form a trans ring junction with chair conformation with two methyl groups in axis positions, the anhydride ring is planar. Crystal water existed in the molecular and stabilized the structure through intermolecular hydrogen bonds.

[(1R,4aS)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl](piperidin-1-yl)methanone

The title compound, C25H37NO, has been synthesized from (+)-dehydroxadabietic acid. The piperidine ring exhibits a classic chair conformation, whereas the two cyclohexane rings adopt chair and half-chair conformations. The two methyl groups directly attached to the tricyclic nucleus are on the same side of the tricyclic phenanthrene structure.

Amberlyst A-26: an efficient and reusable heterogeneous catalyst for a one-pot oxidation–Cannizarro reaction

Amberlyst A-26 catalyses the efficient synthesis of α-hydroxy-arylacetic acids from aryl methyl ketones in the presence of SeO2. After simple separation, the catalyst does not lose its activity and can be reused without significant loss in activity for at least four cycles.