Synthesis and Crystal Structure of 5,5-Dimethyl-2-(4-chlorophenyl)(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one-2-yl)methyl-3-(4-methoxyphenylamino)-2-cyclohexene-1-one

The title compound 5,5-dimethyl-2-（4-chlorophenyl）（3-hydroxy-5,5-dimethyl- 2-cyclohexen-1-one-2-yl）methyl-3-（4-methoxyphenylamino）-2-cyclohexen-1-one has been synthesized, and its crystal structure was characterized by X-ray single-crystal diffraction. The crystal belongs to monoclinic, space group P21/c with a = 9.4193（13）, b = 26.915（4）, c= 21.188（3） A, β = 101.906（3）°, V = 5256.2（13） A3, Z = 4, C60H68C12N2O8, Mr =1016.06, Dc = 1.284 g/cm3, F（000） = 2160, λ（MoKα） = 0.71073 A, μ = 0.182 mm^-1, R = 0.0530 and wR = 0.1131 for 4128 observed reflections （1 〉 2α（Ⅰ））. X-ray analysis reveals that there are two independent molecules in the unit and the cyclohexenone rings adopt different conformations. In addition, there are four intramolecular hydrogen bonds in the title molecule.

An efficient synthesis of 2,2-bis(1H-indol-3-yl)-2H-acenaphthen-1-one catalyzed by recyclable solid superacid SO_4^(2-)/TiO_2 under grinding condition

An efficient synthesis of symmetrical 2,2-bis（1H-indol-3-yl）-2H-acenaphthen-1-one is achieved via a reaction of acenaphthe-nequinone and indoles catalyzed by solid superacid SO4^2-/TiO2 under solvent-free conditions at room temperature by grinding, which provides an efficient route to the synthesis of symmetrical 2,2-bis（1H-indol-3-yl）-2H-acenaphthen-1-one.This procedure offers several advantages including solvent-free conditions,excellent yields of products,simple work-up as well as reuse of catalysts which makes it a useful and attractive protocol for the synthesis of these compounds.

Synthesis of (1H)-3,4-Dihydropyrrolo[2,1-c][1,4]oxazin-1-one Derivatives

In search of new anti-inflammatory and analgesic agents, (1H)-3,4-dihydro- pyrrolo [2,1-c][1,4]oxazin-1-one (3) and its acyl derivatives were designed and prepared. Compound 3 was prepared by treatment of methyl 1-(2-bromoethyl) pyrrole-2-carboxylate with silver oxide and its derivatives were obtained by Friedel-Craftes reaction. Nine of 6-acyl derivatives of compound 3 were prepared.

Synthesis, Structural Characterization and Antimicrobial Activity of a Novel Cobalt(II) Complex Based on 3-Methyl-1-Phenyl-4-(2-Thienoyl)-Pyrazol-5-One

New cobalt(II) complex, [Co(O2C15H11N2S)2(OH2)2]∙2H2O (1∙2H2O), has been synthesized upon reaction of cobalt chloride hexahydrate (Co(Cl)2∙6H2O) with 3-methyl-1-Phenyl-4-(2-thienoyl)-pyrazol-5-one (referred as HL) in ethanol at room temperature. Single crystal X-ray diffraction (XRD), spectroscopic methods, and microelemental analyses were used to characterize 1∙2H2O. Compound 1∙2H2O crystallizes in the orthorhombic crystal system with a Pbca space group and with the cobalt atom being pseudo-octahedral coordinated. The broth microdilution technique was used to screen the free ligand (HL) and the complex (1∙2H2O) for antimicrobial activities. HL has a low activity (MIC > 100 μg/mL) on all microorganisms, whereas compound 1∙2H2O displayed moderate activity (10 ∙2H2O exhibited bactericidal and fungicidal activity respectively on all the bacteria and yeasts tested. These findings reveal that the antimicrobial activity of HL was enhanced upon coordination to Co(II) ion against all microorganisms (bacteria and fungus).

Synthesis, Structural Characterization and Antimicrobial Activity of a Novel Cobalt(II) Complex Based on 3-Methyl-1-Phenyl-4-(2-Thienoyl)-Pyrazol-5-One

New cobalt(II) complex, [Co(O2C15H11N2S)2(OH2)2]∙2H2O (1∙2H2O), has been synthesized upon reaction of cobalt chloride hexahydrate (Co(Cl)2∙6H2O) with 3-methyl-1-Phenyl-4-(2-thienoyl)-pyrazol-5-one (referred as HL) in ethanol at room temperature. Single crystal X-ray diffraction (XRD), spectroscopic methods, and microelemental analyses were used to characterize 1∙2H2O. Compound 1∙2H2O crystallizes in the orthorhombic crystal system with a Pbca space group and with the cobalt atom being pseudo-octahedral coordinated. The broth microdilution technique was used to screen the free ligand (HL) and the complex (1∙2H2O) for antimicrobial activities. HL has a low activity (MIC > 100 μg/mL) on all microorganisms, whereas compound 1∙2H2O displayed moderate activity (10 ∙2H2O exhibited bactericidal and fungicidal activity respectively on all the bacteria and yeasts tested. These findings reveal that the antimicrobial activity of HL was enhanced upon coordination to Co(II) ion against all microorganisms (bacteria and fungus).

The Synthesis of 3-(2'-Hydroxybutyl) isobenzofuran-1 (3H)-one

The synthesis of 3-(2'-hydroxybutyl）isobenzofuran-1(3H)-onel from phthalicanhydride via the intermediate 3-(2'-oxoethyl) isobenzofuran-1(3H)-one 6 was described．

Synthesis,Crystal Structure and Plant Growth Regulatory Activity of 1-(3-Amino-[1,2,4]triazol-1-yl)-3,3-dimethyl-butan-2-one

The title compound 1-（3-amino-[1,2,4]triazol-1-yl）-3,3-dimethyl-butan-2-one（3） was synthesized by Hofmann-alkylation reaction of 1-chloro-3,3-dimethyl-butan-2-one（1） and ~1H-[1,2,4]triazol-3-ylamine（2） with equal amount of K_2CO_3 as acid acceptor. The structure of compound 3 was characterized by ~1H NMR, 13 C NMR, HRMS and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic system, space group P21/n with a = 5.7227（8）, b = 27.924（4）, c = 6.2282（7） ？, β = 101.892（11）°, V = 973.9（2） ？~3, Z = 4, T = 180.00（10） K, μ（MoKα） = 0.087 mm^（-1）, Dc = 1.243 g/cm^3, 3832 reflections measured（3.648≤θ≤26.022°）, 1916 unique reflections（Rint = 0.0359, Rsigma = 0.0572） used in all calculations. The final R = 0.0557（I 〉 2σ（I）） and w R = 0.1276（all data）. Bioassay showed that 3 displayed excellent activity as plant growth regulator with inducing lateral root formation and enhancing primary root elongation at 0.27 mmol/L（50 ppm） in soybeen（He Feng-50）. Good water solubility was found with 50 mg in 1 m L of water. Therefore, application of 3 in agriculture is more environmentally friendly due to cosolvent-free condition, and results in improved abiotic-stress tolerance by affecting the root growth. And furthermore, it can be used as a precursor to investigate the function of regulating plant root growth.

Synthesis and Crystal Structure of 4-Bromo-5-ethoxy-3-methyl-5- (naphthalen-1-yl)-1-tosyl-1H-pyrrol-2(5H)-one

The title compound 4-bromo-5-ethoxy-3-methyl-5-（naphthalen-l-yl）-l-tosyl-lH- pyrrol-2（5H）-one 1 （C24H22BrNO4S, Mr = 500.40） has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21/n with a = 8.8562（15）, b = 18.118（3）, c = 14.055（2）A, β = 99.855（3）^o, V= 2221.9（6）A3, Z = 4, Dc = 1.496 g/cm^3,μ= 1.975 mm^-1, 2 = 0.71073A, F（000） = 1024, R = 0.0607 and wR = 0.1371.

Synthesis and Crystal Structure of a New Quinazolinone Compound 2,3-Dihydro-2-(2-hydroxyphenyl)-3-phenyl-quinazolin-4(1H)-one

A new quinazolinone compound 2,3-dihydro-2-(2-hydroxyphenyl)-3-phenyl- quinazolin-4(1H)-one 3 ([C20H16O2N2]?C2H5OH, Mr = 362.42) and compound 2-(2-hydroxy- benzylidene-amino)-N-phenyl-benzamide 2 (C20H16O2N2, Mr = 316.34) were prepared from a precursor of 2-amino-N-phenyl-benzamide 1 (C13H12ON2, Mr = 212.25). Compound 3 was characterized by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic, space group Pbca with a = 1.2889(11), b = 1.6170(14), c = 1.7729(15) nm, V = 3.695(6) nm3, Z = 8, F(000) = 1536, Mr = 362.42, Dc = 1.303 g/cm3, μ(MoKα) = 0.087 mm-1, R = 0.0447 and wR = 0.0879. The crystal structure analysis indicates that the title compound has a two-dimensional network structure formed by hydrogen bonds and electrostatic interactions.

Novel Copper(II) and Zinc(II) 2-D Supramolecular Structures Based on Carboxylate and 1-Substitutedimidazole Mixed-ligands

Using the ligand bis（3-（1H-imidazol-1-yl）-1-phenylpropan-1-one） L, two novel complexes [CuL2（ph））]·H2O 1 and [ZnL2（tp）] 2 （ph = phthalic acid, tp = terephthalic acid） have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction analysis. Crystal data for 1： triclinic, space group P1^-, a = 9.4300（17）, b = 12.148（2）, c = 13.721（2） A, a = 109.620（2）,β = 94.351（2）, y = 94.830（2）°, C32H30N4O7Cu, Mr = 646.14, V= 1466.2（4） A^3, Z = 2, Dc = 1.464 g/cm3, It（MoKa） = 0.801 mm^-1, F（000） = 670, the final R = 0.0337 and wR = 0.0859 for 5122 observed reflections with I 〉 2σ（I）, And those for 2： monoclinic, space group P2/n, a = 7.1866（11）, b = 14.144（2）, c = 14.407（2）/k, β = 101.427（2）°, C32H28N4O6Zn, Mr = 629.95, V = 1435.4（4） A3, Z = 2, Dc = 1.457 g/cm3, μ（MoKa） = 0.908 mm^-1, F（000） = 652, the final R = 0.0438 and wR= 0.0821 for 2546 observed reflections with I〉 2σ（I）. In 1 and 2, ph or tp ligauds bridge the six-coordinated copper（Ⅱ） or four-coordinated zinc（Ⅱ） ions forming 1D zigzag chains while L ligands act as the terminal monodentate ligand. It is noted that weak non-classical C-H…O plays the important and dominating roles in the formation of 2D supramolecular architectures of 1, but in 2 non-classical C-H…O and aromatic π…π Stacking interactions are quite important and play dominant roles in the self-assembly of 2D supramolecular architectures.

Three component reactions: An efficient and green synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones and thiones using silica gel-supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate

An environmentally benign aqueous protocol for the synthesis of 3,4-dihydropyrimidin-2-（ 1 H）-ones and thiones promoted by a green catalyst, silica gel-supported L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate, has been developed. The use of nontoxic, thermally stable and inexpensive amino acid catalyst makes the process simple with minimal amount of chemical waste. Compared with classical Biginelli reaction conditions, this new method has the advantages of high yields and simple workup procedures.

Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

A series of 2-（arylmethylidene）-2,3-dihydro-1-benzofuran-3-one derivatives（aurones, 1–20） were synthesized and screened for their inhibitory activity against h MAO. Seventeen compounds（1–5, 7–17,19） were found to be selective towards h MAO-B, while two were non-selective（6 and 20） and one（18）selective towards h MAO-A. Compound 17（Ki = 0.10 0.01 mmol/L） was found to be equally potent and selective towards h MAO-B, when compared with the standard drug Selegiline（Ki = 0.12 0.01 mmol/L）.Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences h MAO-B inhibitory potency, while their structural bulkiness influences selectivity between h MAO-A and h MAO-B.Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity.

苏木心材中一个新黄酮类化合物

目的:从苏木Caesalpinia sappan中寻找新的活性成分。方法:用溶剂萃取及硅胶正相色谱进行活性成分的分离纯化,根据理化性质、光谱数据进行结构鉴定。结果:从苏木95%乙醇提取物中分离得到了9个化合物:3,8-dihydroxy-4,10-dimethoxy-7-oxo-[2]benzopyrano[4,3-b][1]benzopyran-7-(5H)-one(1),3-deoxysappanchal-cone(2),sappanchalcone(3),3-deoxysappanone B(4),鼠李素(rhamnetin,5),原苏木素C(protosappanin C,6),3,7-di-hydroxy-chroman-4-one(7),己二酸二甲酯(8),胡萝卜苷(daucosterin,9)。结论:化合物1为新化合物,化合物7,8为首次从该植物中分离得到。药理筛选结果表明,化合物3对多种癌细胞株具有一定的抑制活性。

UPLC-Q/TOF法同时定性定量分析滇芹药材中主要化学成分

目的建立UPLC-Q/TOF法同时定性、定量分析滇芹中主要化学成分。方法采用超高效液相色谱串联飞行时间质谱法进行分析,色谱柱为Agilent Poroshell 120 Hilic,流动相为乙腈-0.1%甲酸水溶液,梯度洗脱,体积流量0.3 m L/min;定性、定量采用Q-TOF正负离子全扫描+IDA(信息关联采集)模式。结果利用已建立的筛查数据库将满足质量误差小于5×10-6、同位素分布正确且含有二级碎片的离子作为分析目标化合物,结合软件Formula Finder、Mass Calculators等功能、在线数据库(Human Metabolome Database、Pub Chem、Chemical Book等)及二级碎片裂解规律,共鉴定出23个化合物,滇芹首次发现4个化合物。确定阿魏酸为定量分析指标性成分,其定量、定性离子分别为178和149;阿魏酸检测质量浓度线性范围为1.14~1 140 ng/m L(r=1.000),检测限、定量限分别为0.87、2.91 ng/m L,精密度、稳定性、重复性试验的RSD<2%,加样回收率为98.13%~101.25%(RSD=1.37%,n=5)。结论该方法灵敏度高、重现性好,分析快速、准确、可靠,可用于同时定性、定量检测滇芹药材中主要化学成分;云南滇芹中阿魏酸含量要高于西藏滇芹。

新鲜烟叶中的1个新二萜类成分

目的研究烟草Nicotiana tabacum叶中的西松烷二萜类化学成分。方法采用柱色谱技术对烟草的95%乙醇提取物进行分离纯化,采用波谱技术结合化学方法进行结构鉴定。结果从烟草提取物中分离得到了5个西松烷二萜类成分,分别鉴定为(1R,3E,7E,10S,11E)-3,7,11-cem-bratriene-10,15-diols(1)、(1S,2E,4S,6R,7E,10E,12S)-2,7,10-cembratriene-4,6,11-triol(2)、(1S,2E,4R,6R,7E,10E,12S)-2,7,10-cembratriene-4,6,11-triol(3)、(1S,2E,4S,6R,7E)-4,6,11-trihydroxy-1-isopropyl-4,8-dimethylpentadeca-2,7-dien-12-one(4)、(1S,2E,4R,6R,7E,11S,12S)-11,12-epoxy-2,7-cembradiene-4,6-diol(5)。结论化合物1为1个新化合物,命名为烟叶二萜B;化合物4首次在植物中发现,为1个新的天然产物。