Synthesis,Crystal Structure and Antitumor Activity of a New Indolequinone Derivative of Ursolic Acid

The title compound（C（37）H（48）BrNO5, 6） was synthesized from ursolic acid and its crystal structure was determined by single-crystal X-ray diffraction analysis. The compound is of orthorhombic system, space group P212121 with a = 16.846（3）, b = 18.844（4）, c = 11.262（2）A, Z =4, V = 3575.1（13） A^3, Mr = 666.67, Dc = 1.239 Mg/m^3, S = 1.002, μ = 1.190 mm^-1, F（000） = 1408,the final R = 0.0831 and wR = 0.1459 for 2286 observed reflections（I 〉 2σ（I））. The crystal structure is stabilized by two intermolecular hydrogen bonds（N–H（0A）···O（2） and O（1）–H（1A）···O（3））. In the preliminary antitumor assay, the title compound 6 exhibits potent cytotoxic activity against Hep G2 and SMMC-7721 cells with IC50 values of 1.64 ± 0.21 and 1.22 ± 0.13 μM, respectively.

Synthesis, Crystal Structure and Antitumor Activity of 4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)-N-(2-hydroxy-3,5-diiodinebenzyl)-thiazol-2-amine

The title compound, 4-（tert-butyl）-5-（1 H- 1,2,4-triazol- 1 -yl）-N-（2-hydroxy-3,5-diio- dinebenzyl）thiazol-2-amine, was synthesized via the reduction of 4-（tert-butyl）-5-（1H-l,2,4- triazol-l-yl）-N-benzylidene-thiazol-2-amine with NaBH4, and its crystal structure was determined by single-crystal X-ray diffraction. The compound crystallizes in monoclinic system, space group P21/c with a = 7.91944（19）, b = 10.5250（3）, c = 24.4985（6） A, Z = 4, V = 2041.66（9） A3, Mr = 599.22, Dc = 1,949 Mg/m3, S = 1.120, p = 3.203 mm-1, F（000） = 1152, the final R = 0.0283 and wR = 0.0592 for 3490 observed reflections （I 〉 2σ（I））. X-ray analysis displays that the crystal water takes part in three intermolecular hydrogen bonds of O（2）-H（2A）…O（1）, O（2）-H（2B）…N（I） and N（5）-H（5）…O（2）, and an octatomic ring R^（8） is formed via intramolecular hydrogen bond of O（I）-H（IA）…N（4）. Furthermore, the I…I contacts are involved in stabilizing the overall three-dimensional network structure. The preliminary biological test shows the title compound has good antitumor activity with the IC50 value of 26 μM against the Hela cell line.

Synthesis,Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole

The title compound 6-chloro-l-（（6-chloropyridin-3-yl）methyl）-3-phenyl-lH-benzofuro[3,2-c]pyrazole（5,C21H13Cl2N3O,Mr = 394.26） was synthesized and characterized by elemental analysis,^1H NMR,^13C NMR and X-ray single-crystal diffraction.The structure reveals that the crystal belongs to the triclinic system,space group P1 with a = 7.8829（8）,b = 10.3281（10）,c = 11.7615（12）A°,α = 83.5552（2）,β = 79.921（2）,γ = 70.189（2）°,V= 885.54（15） A°3,Z = 2,Dc =1.479 g/cm^3,μ = 0.383 mm^-1,F（000） = 404,R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I 〉 2σ（I）.The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction.In addition,the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.

Synthesis, Crystal Structure and Antitumor Activity of (E)-1-(7-Methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5- yl)-3-(2-methoxyphenyl)-2-(1H-1,2,4-triazol-1-yl)propenol

The title compound, （E）-1-（7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl）- 3-（2-methoxyphenyl）-2-（1H-1,2,4-triazol-1-yl）propenol （3a）, was synthesized by the Aldol con- densation reaction of 1-（7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl）-2-（1,2,4-triazol- 1-yl）ethanone with 2-methoxybenzaldehyde and then reduced with NaBH4, and its crystal structure was determined by single-crystal X-ray diffraction： monoclinic system, space group P21 with a = 6.2002（3）, b = 12.8452（7）, c = 13.2257（7） ？, Z = 2, V = 1031.23（9） ？3, Mr = 407.46, Dc = 1.312 Mg/m3, S = 1.054, μ = 0.091 mm-1, F（000） = 432, the final R = 0.0353 and wR = 0.0769 for 3161 observed reflections （I 〉 2σ（I））. X-ray analysis displays that the title compound adopts an E configuration for the C（7）=C（8） double bond and S configuration for the chirality center with the specific rotation of –63.75°. Furthermore, the stability of the crystal was maintained through the intermolecular hydrogen bond O（1）–H？？？N（3）. The antitumor assay exhibits that the title compound 3a （E configuration） has a good antitumor activity against the Hela cell line with the IC50 value of 36.9 μM, which is better than that of 3b （Z configuration）.

Synthesis,Crystal Structure and Antitumor Activity of Tectochrysin-6-sulfonate

In order to enhance water-solubility and biological utilization rate of tectochrysin,sodium 5-hydroxyl-7-methoxyflavone-6-sulfonate（1） was synthesized and its structure was identified on the basis of ^1 H NMR,FT-IR and elemental analysis.5-Hydroxyl-7-methoxyflavone-6-sulfonate was assembled with Ni（II） or Mn（II）,hexaquanickel（II） bis（5-hydroxyl-7-methoxyflavone-6-sulfonate） tetrahydrate（2） and hexaquamanganese（II） bis（5-hydroxyl-7-methoxyflavone-6-sulfonate） tetrahydrate（3） were obtained and characterized by IR spectroscopy.The crystal structures of 2 and 3 were determined by X-ray single-crystal diffraction analysis.The results showed that 2 and 3 are isomorphous crystals and crystallize in monoclinic crystal system,space group C2/c.In 2 and 3,the supramolecular structures are organized into hydrophilic and hydrophobic regions.Hydrophilic regions are generated by O–H？？？O hydrogen bonds among sulfonate groups,latticed water molecules and coordinated water molecules.The π-π stacking interactions assemble the flavone skeletons into columns and these columns form hydrophobic regions.The sulfonate groups play an important role as a bridge of the hydrophilic and hydrophobic regions as well as the inorganic and organic components.Three-dimensional networks of 2 and 3 are furnished by extensive array of hydrogen bonds,π-π stacking interactions and electrostatic interactions.The anti-proliferative activities of 1-3 in vitro against human leukemia cells K562 and human lung cancer cells A549 were evaluated by the standard MTT assay.The pharmacological activity results showed that the introduction of sulfonic acid groups enhanced the antitumor activity of tectochrysin.

Synthesis, Crystal Structure and Antitumor Activity in Vitro of a New Benzoate Binuclear Cupper(Ⅱ ) Complex

The title compound, [Cu2（C7H5O2）4（C2H6O）2], was synthesized by the reaction of benzoic acid, copper acetate and ethanol in an aqueous solution. Trypan blue dye exclusion method was used in experiment. X-ray single-crystal analysis has revealed that compound 1 （C32H32Cu2O10） crystallizes in the monoclinic system, space group C2/c, Mr = 703.66, a = 47.340（5）, b = 6.6613（4）, c = 22.028（2）A,β = 113.284（4）°, V = 6380.6（10） A^3, Z = 8, Dc= 1.465 g/cm^3, F（000） = 2896,μ = 1.388 mm^-11, the final R = 0.0515 and wR = 0.1172 for 5712 observed reflections with I 〉 2σ（I）. X-ray crystal structure analysis suggests that compound [CH2（C7H5O2）4（C2H6O）2] has a binuclear structure with two Cu（II） atoms coordinated by four benzoate groups and two ethanol molecules. The crystal packing is stabilized by intermolecular O-H...O hydrogen bonds. The compound inhibits the proliferation of K562 cells （chronic myeloid leukemic cells） significantly and dose-dependently in 48 h, and IC50 of K562 is 17.3μg/mL by trypan blue dye exclusion method.

Crystal Structure and Antitumor Activity of Tri[2- [N-(4'-methyl-benzylsulfonyl)amino]ethyl]-amine

The crystal structure of the title compound (C27H38N4O7S3, Mr = 626.79) has been determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group Pīwith a = 9.411(1), b = 11.645(2), c = 14.672(2) , a = 91.80(1), b = 95.36(1), g =104.56(1)o, V = 1547.0 3, Z = 2, Dc = 1.346 g/cm3, l = 0.71073 , m(MoKa) = 0.289 mm-1 and F(000) = 664. The structure was refined to R = 0.0406 and wR = 0.1177 for 4103 observed reflections with I > 2s(I). X-ray diffraction analysis reveals that the title compound is a practically distorted tetrahedron and each molecule contains one lattice H2O by hydrogen bond. The antitumor activity of the title compound against HL-60 human leukemia cells has also been studied by MTT method.

Synthesis,Crystal Structure and Antitumor Activity of Mixed Ligand Coordination Compound of Copper with Norfloxacin and 1,10-Phen,[Cu(NFLX)(phen)(H2O)]NO3·3H2O

The mixed ligand coordination compound of copper with norfloxacin (NFLX) and 1, 10-phen has been synthesized and characterized by means of X-ray single crystal diffraction. The structure features of the coordination compound are described. Antibacterial activities of the coordination compound have been tested against different microorganisms. The antitumor activities of the coordination compound on leukemia HL-60 cell line and liver cancer BEL-7402 cell line have been measured, respectively. The results indicated that the coordination compound has strong inhibitory effect on HL-60 and BEL-7402 cell lines.

Synthesis, Crystal Structure and Antitumor Activity of N-[5-(Benzylthio)-1,3,4-thiadiazol-2-yl]-4-chlorobenzamide

The title compound N-[5-（benzylthio）-1,3,4-thiadiazol-2-yl]-4-chlorobenzamide（C（16）H（12）ClN3OS2, Mr = 361.86） was designed and synthesized as anticancer agent, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to triclinic, space group P1 with a = 5.7417（10）, b = 9.8057（17）, c = 14.330（3） A, a = 91.987（3）, b = 97.154（3）, γ = 93.402（3）°, V = 798.4（2） A3, Z = 2, Dc = 1.505 g/cm^3, μ = 0.507 mm-1） F（000） = 372, the final R = 0.0481 and wR = 0.1290 for 2064 observed reflections with I 〉 2s（I）. In the crystal packing, the molecules form stacks by a three-dimensional framework, which results from intermolecular N（1）-H（1）···N（2） and C（5）-H（5）···N（3） hydrogen bonds together with π-π stacking interactions between the thiadiazole and chlorobenzene rings. The title compound was found to exhibit more potent in vitro antitumor activities against the four tested cancer cell lines than sorafenib.

Synthesis, Crystal Structure and Antitumor Activity of (E)-4-tert-Butyl-N-(2,4-dichlorobenzylidene)-5-(1,2,4-triazol-1-yl)-thiazol-2-amine

The title compound （E）-4-tert-butyl-N-（2,4-dichlorobenzylidene）-5-（1,2,4-triazol-1-yl）-thiazol-2-amine was synthesized by the reaction of 4-tert-butyl-5-（1,2,4-triazol-1-yl）-thiazol-2-amine with 2,4-dichlorobenzaldehyde, and its crystal structure was determined by singlecrystal X-ray diffraction. The crystal belongs to the triclinic system, space group P1 with a = 7.9748（4）, b = 10.1803（5）, c = 11.4603（6）, α = 102.882（1）, β = 100.253（1）, γ = 104.457（1）°, V = 850.95（7）3, Z = 2, F（000） = 392, C16H15Cl2N5S, Mr = 380.29, Dc = 1.484 g/cm3, S = 1.095, μ = 0.512 mm-1, the final R = 0.0301 and wR = 0.0965 for 3334 observed reflections （I 〉 2σ（I））. The preliminary antitumor activity shows that for the title compound the IC50 of Hela is 0.175 μmol/mL and that of Bel7402 is 0.156 μmol/mL.

Synthesis,Crystal Structure and Antitumor Activity of N-(4-tert-butyl-5-(4-chlorobenzyl)thiazol-2-yl)-2,6-difluorobenzamide

The title compound was synthesized by the reaction of 4-tert-butyl-5-（4-chlorobenzyl）-2-aminothiazole with 2,6-difluorobenzoic acid. The crystal structure of the title compound, C21H19ClF2N2OS, was determined by single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group Pbca with a = 12.6479（13）, b = 13.1204（13）, c = 14.1341（15）, Z = 4, V = 2011.5（4）3, Mr = 420.89, Dc = 1.390 g/cm3, S = 1.023, μ = 0.326 mm-1, F（000） = 872, the final R = 0.0365 and wR = 0.0880 for 6101 observed reflections（I 〉 2σ（I））, and R = 0.0507, wR = 0.0978 for 7779 independent reflections. X-ray crystal structure displays that the hydrogen bonding interactions observed link the molecules to form a dimeric unit. The preliminary biological test of the title compound shows good antitumor activity, with IC50 of 0.046 μmol/mL against the Hela cell line.

Synthesis,Crystal Structure and Antitumor Activity of a Novel Zn(Ⅱ)Complex with 2-(Nicotinoyloxy)acetic Acid Ligand

A novel Zn（Ⅱ） complex, [ZnL2（H2O）4]·H2O（1, HL = 2-（nicotinoyloxy）acetic acid）, was synthesized using Zn（OAc）2·2H2O and 2-（nicotinoyloxy）acetic acid as raw materials. Its structure has been elucidated by elemental analysis, IR and single-crystal X-ray diffraction. The structural analysis revealed that complex 1 crystallizes in triclinic, space group P1 and the Zn（Ⅱ） atom is six-coordinated with two N atoms from two different 2-（nicotinoyloxy）acetate anion ligands and four O atoms from coordinated water molecules. Complex 1 forms a 3D network structure by O–H···O hydrogen bonds. The antitumor activities of 2-（nicotinoyloxy）acetic acid ligand and its Zn（Ⅱ） complex were evaluated against human lung adenocarcinoma A549 cells, human hepatoma SMMC-7721 cells and human colon carcinoma Wi Dr cells.

Synthesis, Crystal Structure and Antitumor Activity of 4-tert-Butyl-N-(2-fluorophenyl)-5- (1H-1,2,4-triazol-1-yl)-thiazol-2-amine

The title compound has been synthesized by the reaction of 1-bromo-3,3-dime- thyl- 1 - （1 H- 1,2,4-triazol- 1 -yl）butan-2-one with 1 -（2-fluorophenyl）thiourea, and its crystal struc- ture was determined by single-crystal X-ray diffraction. The crystal belongs to the orthorhombic system, space group Pbca with a = 15.2568（6）, b = 12.1533（5）, c = 16.7307（7） A, Z = 8, V = 3102.2（2） A3, Mr = 317.39, Dc = 1.359 g/cm3, S = 1.05, μ = 0.223 mm-1, F（000） = 1328, the final R = 0.034 and wR = 0.097 for 2590 observed reflections （I 〉 2σ（I））. X-ray crystal structure presents the intramolecular N-H…N hydrogen bond, which plays an important role in stabilizing the crystal structure. In addition, the preliminary biological test on the title compound shows good antitumor activity, with IC50 of 0.122 μmol/mL against the Hela cell line.

Synthesis, Crystal Structure and Antitumor Activity of 6,7,8-Trimethoxy-1-(4-methoxy-3-nitrophenyl)-4- (pyridin-4-ylmethyl)-3,4-dihydroisoquinoline

A novel class of 3,4-dihydroisoquinolines （7a～e） was designed, synthesized and characterized by IR, NMR and ESI-MS. The crystal structure of compound 7a （6,7,8-trime- thoxy-1-（4-methoxy-3-nitrophenyl）-4-（pyridin-4-methyl）-3,4-dihydroisoquinoline, C25H25N3O6, Mr=463.48） was determined by X-ray diffraction analysis. The crystal belongs to the monoclinic system, space group P21/n with a=12.074（5）, b=12.896（6）, c=15.450（7）, β=105.846（5）°, V=2314.4（17） 3, Z=4, Dc=1.330 Mg/m3, μ（MoKα）=0.096 mm-1, F（000）=976, S=0.991, the final R=0.0467 and wR=0.1231 for 4545 unique reflections （Rint=0.0656） with 3117 observed ones. The bioassay showed that compounds 7a～e exhibit moderate antitumor activities in vitro.

Synthesis, Crystal Structure and Antitumor Activity of a Na(Ⅰ) Coordination Polymer Based on 2-Propyl-4,5-imidazoledicarboxylic Acid and 1,10-Phenanthroline Ligands

A new Na(I) coordination polymer,[Na2(Hpimdc)(H2 pimdc)(phen)2]n(1), has been synthesized by the reaction of NaOH with 2-propyl-4,5-imidazoledicarboxylic acid(H3 pimdc)and 1,10-phenanthroline(phen). The Na(I) coordination polymer 1 was characterized by single-crystal X-ray diffraction analysis and elemental analysis. In 1, the bridged ligand H3 pimdc adopts two modes(singly deprotonated and doubly deprotonated) to coordinate with the Na(I) ion.The Na(1) ion is six-coordinated with three N atoms from a phen ligand and a H2 pimdc ligand,three O atoms from a Hpimdc ligand and two other different H2 pimdc ligands. The Na(2) ion is also six-coordinated with three N atoms from a phen ligand and a Hpimdc ligand, three O atoms from a H2 pimdc ligand and other two different Hpimdc ligands. Complex 1 exhibits a 1 D chain structure built up by μ-H2 pimdc-and μ-Hpimdc2-ligands. The antitumor activities of complex 1 against human SGC7901, A549 and H08910 cells have been tested.

Synthesis, Crystal Structure and Antitumor Activity of N-(5-Aryl-1,3,4-thiadiazol-2-yl)-N?-((E)-styryl)ureas

N-(5-Aryl-1,3,4-thiadiazol-2-yl)-N?-((E)-styryl)ureas 4 a^4 i were designed and synthesized as antitumor agents, and their structures were characterized by IR, 1 H NMR, 13 C NMR,MS and elemental analysis. The single crystal of compound 4 a, C17 H13 FN4 OS, was also determined by X-ray crystallography. Crystal data: monoclinic, space group P21/n, a = 4.9401(8), b= 8.7100(15), c = 36.604(6) A,β= 93.320(3)°, V = 1572.4(5) A3, Z = 4, F(000)= 704, Dc = 1.438 g/cm3,μ= 0.228 mm-1, R = 0.0600 and wR = 0.1448 for 2743 independent reflections(Rint =0.0418) and 2174 observed ones(I > 2σ(I)). The in vitro antitumor activities of compounds 4 a^4 i were preliminarily evaluated by the standard MTT assay.

Synthesis, Crystal Structure and Antitumor Activity of 4-(5-(2,6-Difluorophenyl)-1,3,4-oxadiazol-2-ylthio)-2-(trifluoromethyl)thieno[2,3-d]pyrimidine

The title compound 4-(5-(2,6-difluorophenyl)-1,3,4-oxadiazol-2-ylthio)-2-(trifluoromethyl)thieno[2,3-d]pyrimidine(C15H5F5N4OS2, Mr = 416.35) was designed and synthesized as antitumor agent, and its structure was determined by 1H NMR, 13C NMR, MS, elemental analysis and single-crystal X-ray diffraction. The crystal belongs to monoclinic system, space group P21/c with a = 9.904(2), b = 10.057(2), c = 16.595(3) ?, β = 100.000(3)°, V = 1627.9(6) ?3, Z = 4, F(000) = 832, Dc = 1.699 g/cm3, μ = 0.395 mm-1, R = 0.0468 and wR = 0.1255 for 4726 independent reflections(Rint = 0.0336) and 2847 observed ones(I > 2σ(I)). The in vitro antitumor activity of the title compound was preliminarily evaluated by the standard MTT assay.

Synthesis, Crystal Structure and Antitumor Activity of 3,3-(1,4-Phenylene)-bisfuro[3,2-d]pyrimidin-4(3H)-ones

3,3-(1,4-Phenylene)-bis(polysubstituted furo[3,2-d]pyrimidin-4(3 H)-ones 3 were synthesized from the starting material of functionalized iminophosphorane 1 by aza-Wittig reaction. All of the title compounds were characterized by 1H NMR, MS and elemental analysis. Meanwhile, the single crystal of compound 3 c, C46H68N6O10, was also obtained and determined by X-ray crystallography. Crystal data: triclinic, space group P1, a = 9.0017(3), b = 10.5908(4), c = 14.0116(5) A, α = 108.582(2)°, β = 94.296(1)°, γ = 105.059(2)°, V = 1204.40(7) ?3, Z = 1, F(000) = 466, Dc = 1.193 g/cm3, μ = 0.084 mm-1, R = 0.0998 and wR = 0.2146 for 4213 independent reflections(Rint = 0.0689) and 2796 observed ones(I > 2σ(I)). The in vitro antitumor activities of compounds 3 a^3 c were preliminarily evaluated by the standard MTT assay.

Design,Synthesis and Crystal Structure of the Antitumor Agent N1-(2-(4-Methoxy-2-nitrophenoxy)-2-dimethyl acyloxymethyl)-5-fluorouracil

A series of novel 5-fluorouracil derivatives were designed and synthesized, and the compound N1-（2-（4-Methoxy-2-nitrophenoxy）-2-dimethyl acyloxymethyl）-5-fluorouracil（C（16）H（16）FN3O8, Mr = 397.32） was structurally characterized by 1H-NMR, 13C-NMR, ESI-MS and single-crystal X-ray diffraction. The compound crystallizes in triclinic, space group P1 with a = 5.6725（7）, b = 8.7443（19）, c = 18.116（3） ？, α = 98.226（17）, β = 96.247（12）, γ = 94.318（14）°, V = 880.3（3） ？~3, Z = 2, T = 294.12（10） K, μ（Mo Kα） = 0.128 mm^（-1）, Dc = 1.499 g/cm3, F（000） = 412 and GOOF = 1.105. 5175 reflections were measured（6.868≤2θ≤52.042°）, and 3416 were unique（Rint = 0.0272, Rsigma = 0.0579） and used in all calculations. The final R = 0.0551（I 〉 2σ（I）） and w R = 0.1288（all data）. The structure of the crystal was stabilized by hydrogen bonds and the antitumor activity of the compound was analyzed by MTT assay.

Synthesis,Crystal Structure,Antitumor Activities and Docking Study of 1-(2-(1H-Indol-3-yl)ethyl)-3-(2-methoxyphenyl)urea

The title compound,1-（2-（1 H-indol-3-yl）ethyl）-3-（2-methoxyphenyl）urea（C（18）H（19）N3O2,Mr = 309.36） has been synthesized,and its structure was characterized by ^1H-NMR,^13C-NMR,ESI-MS and single-crystal X-ray diffraction.It crystallizes in the monoclinic space group P21/c with a = 16.2774（15）,b = 11.1082（10）,c = 9.0819（3） A,β = 103.09（9）°,V = 1599.5（3） A^3,Z = 4,T = 293（2） K,μ（MoKα） = 0.086 mm^（-1,Dc = 1.285 g/cm^3,F（000） = 656 and GOOF = 0.981.5973 reflections were measured（7.04≤2θ≤52.04°）,and 3143 were unique（Rint= 0.0393,Rsigma = 0.0546） and used in all calculations.The final R = 0.0756（I 〉 2σ（I）） and w R = 0.1976（all data）.The antitumor activity of the title compound was analyzed by MTT assay.Meanwhile,to rationalize its potencies in the CDK4 target,the title compound was docked into CDK4 protein and the interactions with the active site residues were analyzed.