Synthesis,Crystal Structure and Antitumor Activity of a New 3H-Phenanthro-[2,1-d]imidazole Derivative of Dehydroabietic Acid

The title compound （CI9H24BrN302, 3） was synthesized from dehydroabietic acid and its crystal structure was determined by single-crystal X-ray diffraction. The compound is of monoclinic system, slSace group C2 with a = 24.830（5）, b = 7.1410（14）, c = 13.981（3） A, p = 107.68（3）°, Z = 4, V= 2361.9（8） A3, Mr = 482.42, Dc = 1.357 Mg/m3, S = 1.003,μ = 1.772 mm1, F（000） = 1008, the final R = 0.0660 and wR = 0.1402 for 2244 observed reflections （I 〉 2o（/））. The crystal structure is stabilized by four hydrogen bonds （O（W）-H（WA）...O（3）, O（W）-H（WB）...O（1）, N（2）-H（2A）...O（W） and N（3）-H（3A）...N（1）） formed among the title compound, the crystal water and acetone molecules. The preliminary antitumor assay showed the title compound exhibited considerable inhibitory activity against HepG2 and SMMC-7721 cell lines with the ICs0 values of 17.1 and 10.2 μM, respectively.

Two Dehydroabietic Acid-based Arylamines: Synthesis, Crystal Structure and Fluorescent Properties

Two dehydroabietic acid-based arylamines have been synthesized and characterized by FTIR, 1H NMR, 13C NMR, MS spectra and elemental analysis. Their spatial structures were determined by X-ray diffraction analysis. UV-Vis absorption and fluorescence spectral characteristics of these compounds in methanol were investigated. Their fluorescence emission spectra in different polarity solvents were further evaluated. Fluorescent properties and structural relationship of the compounds showed that fluorescence intensity and quantum yield inversely increase with the non-coplanar degree. In addition, the solvent polarity has different effects on the fluorescence emission spectra of two compounds.

Syntheses and Crystal Structures of 12-Oxime Dehydroabietic Acid Derivatives

Three novel dehydroabietate oxime derivatives were synthesized from dehydroabietic acid and their crystal structures were determined by X-ray crystallographic techniques. All of these 12-oxime dehydroabietic acid derivatives crystallize in orthorhombic system, space group P212121. In the structures, rings A and B exhibit chair and half-chair configurations, respectively and form trans ring junction with two methyl groups（C（19） and C（20）） in the axis positions. The oxime groups have E conformations. Comparison of conformations reveals subtle differences principally in ring B due to the modification in C（12）. The E-acetaldehyde oxime derivative 2c showed distinct BKα gate-opening activity with an ionic current increase of 164% at 30 μM versus the control current.

Synthesis,Crystal Structure and Cytotoxic Activity of a New N-Vinyl-1H-dibenzo[a,c]carbazole Derivative of the Dehydroabietic Acid

The title compound （C29H33NO2, 3） was synthesized and structurally characterized by elemental analysis, IR, MS, 1H- and 13C-NMR and single-crystal X-ray diffraction. The crystal is of monoclinic system, space group P21 with a = 14.428（3）, b = 7.3440（15）, c = 22.768（5） A, β = 95.17（3）°, V = 2402.7（8） A3, Z = 4, Mr = 427.56, Dc = 1.182 g/cm3, F （000） = 920, 2（MoKa） = 0.71073 A,μ = 0.073 mm-1, the final R= 0.0670 and wR= 0.1002 for 2437 reflections with I〉 2σ（I） Two crystallographically independent molecules with different conformations co-exist in the structure. The crystal structure is stabilized by intermolecular C-H…π interactions which make the molecules stack along the b axis. In addition, the preliminary cytotoxic assay showed that the title compound exhibited moderate inhibitory activity against KB and SW1116 cells.

Dehydroabietic acid chemosensitizes drug-resistant acute lymphoblastic leukemia cells by downregulating survivin expression

Objective:To explore the mechanism of drug resistance in acute lymphoblastic leukemia and the anti-tumor effect of combination therapy of dehydroabietic acid and vincristine against acute lymphoblastic leukemia cells.Methods:Acute lymphoblastic leukemia cells REH and CCRFCEM were employed to detect the anti-tumor effect of vincristine and doxorubicin on proliferation and apoptosis using EdU assay,human active caspase-3 Quantikine ELISA kit,and flow cytometry.Vincristine-resistant REH cells(REH-R),survivin knockdown and overexpressing REH cells were established to verify the role of survivin in drug resistance.Additionally,in vitro and in vivo assays were performed to determine the effect of dehydroabietic acid on the cytotoxicity of vincristine.Results:Vincristine and doxorubicin markedly suppressed proliferation and induced apoptosis of REH and CCRF-CEM cells.Survivin expression was upregulated in REH-R cells compared with REH cells.Knockdown of survivin expression obviously restored the sensitivity of REH-R cells to vincristine.Akt phosphorylation was also increased in REH-R cells compared to REH cells.In addition,LY294002,a PI3k/Akt pathway blocker,inhibited survivin expression and enhanced cytotoxicity of vincristine to REH-R cells.Dehydroabietic acid effectively reduced survivin expression in REH-R cells,thereby enhancing the therapeutic effect of vincristine on drug-resistant cells.Survivin overexpression markedly reduced the effect of dehydroabietic acid on enhancing the anti-proliferation and inducing apoptosis effect of vincristine.Moreover,the combination of dehydroabietic acid with vincristine significantly extended the survival rate in a mouse xenograft model of acute lymphoblastic leukemia,compared with vincristine treatment alone.Conclusions:Dehydroabietic acid may be used as a potential candidate for the treatment of acute lymphoblastic leukemia in combination with vincristine.

Synthesis and Crystal Structure of a Novel Lactone Derived from Dehydroabietic Acid

A novel lactone derived from dehydroabietic acid,C20H21BrO4,has been charac-terized by IR,1H NMR,13C NMR and single-crystal X-ray diffraction method.It crystallizes in orthorhombic,space group P212121 with a = 6.4195（15）,b = 11.535（3）,c = 24.654（6） ,V = 1825.5（7） 3,Z = 4,Mr = 405.28,Dc = 1.475 g/cm3,λ = 0.71075 ,μ（MoKα） = 2.27 mm-1,F（000） = 832,the final R = 0.024 and wR = 0.045 for 2152 observed reflections with I 2σ（I）.The molecules of lactone are mainly linked through intermolecular hydrogen bonds.

Fluorescent properties and in vitro studies of new dehydroabietic acid-based diarylamines fluorescent probes

A series of dehydroabietic acid-based diarylamines have been synthesized in order to investigate their fluorescent properties, photostability, cell toxicity and in vitro fluorescence imaging. The geometries as well as their molecular properties were optimized at the B3LYP/6-31G~* level using Gaussian 03. The results indicate that molecular geometry, HOMO and LUMO energies, and energy gaps are important to predict absorption and fluorescent properties. Five of the compounds can be effectively taken up by human cervical carcinoma, human hepatocellular carcinoma SMMC-7721, human gastric cancer SGC-7901 and human lung adenocarcinoma A549 cells and strong blue fluorescent signals are detected in these cells. These compounds are potential candidates for fluorescent probes in biological diagnosis.

Syntheses, Crystal Structures, and Electrochemical Properties of Three Anhydrides Based on Ferrocenecarboxylic Acid and Dehydroabietic Acid

Three title compounds(3~5) have been successfully synthesized via interactive reactions between ferrocenecarboxylic and dehydroabietic acids, which can be characterized by FT-IR, elemental analysis, ESI-MS, and NMR spectroscopy. The crystal structures of compounds 4 and 5 can be determined by single-crystal X-ray diffraction. Compound 4 is of orthorhombic system, space group P212121 with a = 7.7010(5), b = 11.7542(9), c = 28.3173(18) ?, Z = 4, V = 2563.3(3) ?~3, Mr = 512.45, Dc = 1.328 g/cm^(-1), S = 1.041, μ = 0.619 mm^(-1), F(000) = 1088, the final R = 0.0396 and wR = 0.0945 for 4394 observed reflections(I > 2σ(I)). Compound 5 crystallizes in orthorhombic system, space group P21212 as well, with parameters of a = 11.9875(15), b = 19.651(2), c = 7.2163(9) ?, Z = 2, V = 1699.9(3) ?~3, Mr = 582.83, Dc = 1.139 g/cm^(-1), S = 1.091, μ = 0.070 mm^(-1), F(000) = 636, the final R = 0.0653 and wR = 0.0719 for 1518 observed reflections(I > 2σ(I)). Additionally, electrochemical properties of compounds 3 and 4 have been investigated by the cyclic and differential pulse voltammogram techniques.

Synthesis and BK channel-opening activity of novel N-acylhydrazone derivatives from dehydroabietic acid

A series of hydrazone and N-acylhydrazone derivatives of dehydroabietic acid were synthesized and evaluated for BK channel-opening activities in an assay system of CHO-K1 cells expressing hBKa channels.The assay results indicated that the activities of the investigated compounds were influenced by the physicochemical properties of the substituent at hydrazone moiety.

Synthesis, Crystal Structure and Antibacterial Activity of New N-(1H-benzo[d]imidazol-2-yl)benzenesulfonamide Derivatives of Dehydroabietic Acid

The title compounds(7a^7g)were synthesized from dehydroabietic acid and characterized by spectroscopic methods including HR-MS,1H-and 13C-NMR.The crystal structure of compound 7g determined by single-crystal X-ray diffractio is of monoclinic system,space group P21 with a=12.282(3),b=9.940(2),c=22.656(5)A,β=103.06(3)°,Z=2,V=2694.4(10)A^3,Mr=1182.95,Dc=1.458 Mg/m^3,S=1.000,μ=1.649 mm^-1,F(000)=1216,the final R=0.0791 and wR=0.1853 for 4098 observed reflections(Ⅰ>2σ(Ⅰ)).The preliminary antibacterial assay showed that compound 7g exhibits significant inhibitory against Bacillus subtilis,Staphylococcus aureus and Methicillin-resistant S.aureus(MRSA)with MIC values of 1.9~7.8μg/mL.

Synthesis and bulk polymerization kinetics of monomer dehydroabietic acid-(2-acryloyloxy-ethoxy)-ethyl ester

A bulk polymerization monomer dehydroabietic acid-(2-acryloyloxy-ethoxy)-ethyl ester(DHADG-AC) was synthesized from dehydroabietic acid(DHA). The chemical structure of DHA-DG-AC was characterized by1~HNMR,(13)~CNMR, MS and FT-IR. The kinetics of the bulk polymerization of DHA-DG-AC was investigated by Differential Scanning Calorimeter(DSC).Two kinds of kinetic model(nth-order model and autocatalytic model) were used to investigate the polymerization process. The results showed that the experim e nt al DSC c u r ve s w e r e c o n si st e nt wi th t he computational data generated by the autocatalytic kinetic model, and the value of E_a was 95.73 k J·mol^(–1).

Syntheses, Crystal Structures, and Electrochemical Properties of Dehydroabietic Acid-based Schiff Bases

Two Schiff bases(DAMBA-Fc and DAA-Fc)derived from dehydroabietic acid have been successfully synthesized and characterized by means of FT-IR,elemental analysis,HRMS,and NMR spectroscopy.The crystal structure of DAA-Fc can be determined by single-crystal X-ray diffraction.The compound is of monoclinic system,space group P21 with a=10.7379(6),b=7.5004(4),c=33.3294(18)?,β=97.996(3)o,Z=4,V=2658.2(3)?3,Mr=481.48,Dc=1.203 g/cm3,S=1.034,μ=0.585 mm-1,F(000)=1032,the final R=0.0566 and wR=0.0701 for 5645 observed reflections(I>2σ(I)).In addition,cyclic and differential pulse voltammogram techniques have been applied to differentiate the redox properties of the aromatic-and aliphatic-connected Schiff bases DAMBA-Fc and DAA-Fc,respectively.

Syntheses, Crystal Structures and Antibacterial Activities of Two New Methyl 12-Alkylamino-13,14-dinitrodeisopropyl-dehydroabietates

The title compounds(5 a and 5 b) were synthesized from dehydroabietic acid and characterized by MS, IR, NMR and elemental analysis. The crystal structure of compound 5 a was determined by single-crystal X-ray diffraction. The compound is of monoclinic system, space group P21 with a = 8.0860(16), b = 14.011(3), c = 9.799(2) ?, β = 106.31(3)?, Z = 2, V = 1065.5(4) ?3, Mr = 431.48, Dc = 1.345 Mg/m3, S = 1.002, μ = 0.099 mm-1, F(000) = 460, the final R = 0.0617 and wR = 0.1532 for 1397 observed reflections(I > 2σ(I)). The preliminary antibacterial assay showed that compound 5 a exhibited considerable inhibitory activity against Bacillus subtilis, Staphylococcus aureus and Methicillin-resistant S. aureus(MRSA) with MIC values of 2～8 μg/mL.