香豆素衍生物的合成及结构表征

合成了11个香豆素衍生物,产率53%—79%,利用元素分析、MS和¹HNMR对其结构进行了表征.同时,由2-氨基苯并噻唑(ABT)和8-甲氧基香豆素-3-甲酸乙酯(MCC)合成了给体-受体加合物ABT-MCC,通过X射线单晶衍射法测定了其晶体结构,晶体属三斜晶系,P1空间群,晶胞参数为:a=9.5978(19)Å,b=10.686(2)Å,c=10.693(2)Å,α=71.30(3)°,β=70.43(3)°,γ=88.99(3)°,V=973.9(3)ų,Z=2,D_x=1.359 mg/m³,μ=0.200 mm^-1,F(000)=416,R=0.0463,wR=0.0992.结果表明,在ABT-MCC晶体中,分子间通过N—H…N和N—H…O氢键作用形成对称的A…D…D′…A′氢键四聚体,并通过弱的C—H…O氢键连接成为一维超分子链状结构,进而分子间通过π-π堆积作用形成层状结构.     

Synthesis and Spectroscopic Study of Coumarin Derivatives

Five new coumarin amide derivatives were synthesized with coupling reagent,the structures of which were characterized by IR,1H NMR,13C NMR,MS and element analysis.Their spectral properties were studied in dichloromethane,in N,N-dimethylformamide(DMF) and in solid state.Solvent polarity has less influence on the UV-Vis maximum absorption at about 430 nm.The maximum emission wavelengths change from 464 nm to 474 nm in dichloromethane,from 476 nm to 482 nm in DMF and from 521 nm to 548 nm in solid state,respec...     

4-羟基香豆素衍生物的荧光性能

4-羟基香豆素衍生物的荧光性能;水杨酸; 羟基香豆素衍生物; 荧光     

Synthesis and Antiproliferative Effect of Halogenated Coumarin Derivatives

A series of 6- and 6,8-halocoumarin derivatives have been investigated as potential antiproliferative compounds against a panel of tumor and normal cell lines. Cytotoxic effects were determined by the MTT method. To investigate the potential molecular mechanism involved in the cytotoxic effect, apoptosis assay, cell cycle analysis, reactive oxygen species (ROS), and reduced glutathione analysis were performed. Among the screened compounds, coumarins 6,8-dibromo-2-oxo-2H-chromene-3-carbonitrile 2h and 6,8-diiodo-2-oxo-2H-chromene-3-carbonitrile 2k exhibited the most antiproliferative effect in thyroid cancer-derived cells TPC-1. The apoptosis assay showed that both 2h and 2k induced apoptosis in TPC-1 thyroid cancer cells. According to these experiments, both coumarins induced a slight increase in TPC-1 cells in the G2/M phase and a decrease in the S phase. A significant increase in ROS levels was observed in TPC-1 treated with diiodocoumarin 2k, while the dibromocoumarin 2h induced a decrease in ROS in a dose and time-dependent manner.     

新型4-羟基香豆素衍生物的合成

以DMSO为溶剂,碳酸二乙酯为酰化试剂,4-取代-2-羟基苯乙酮在氢化钠的催化下,经一步反应合成了7个新型的7-取代-4-羟基香豆素,产率49%~90%,其结构经1H NMR表征。     

Ultrasound Assisted Synthesis of Coumarin Thioglycopyranoside Derivatives

The methyl coumarins reacted with N‐bromo‐succinimide gave compounds ( a～c ) which on further reacted with various peracetyl sulfhydryl glycose ( 1～3 ) afforded a series of novel coumarin thioglycopyranoside compounds ( 1a～1c, 2a～2c, 3a～3c ). And when used ultrasonic irradiation, this method offered several advantages such as good yields and short reaction time than the silent reaction. All the new compounds were characterized on the basis of the IR, ¹H NMR, ¹³C NMR and elemental analysis.     

3-芳基香豆素衍生物的合成及其生物活性研究

对3-芳基香豆素母核进行修饰，以芳基乙酸和水杨醛为起始原料，三乙胺为催化剂，乙酸酐为溶剂，经缩合反应分别引入吸电子基团三氟甲基和给电子基甲氧基，合成了3-(4′-三氟甲基苯基)香豆素（2a）和新化合物3-(4′-甲氧基苯基)香豆素（2b），其结构经UV-Vis、 ¹H NMR、 IR和MS表征。并对其生物活性和荧光标记特性进行了研究。结果表明：2a和2b显示较强的细胞增殖抑制活性、抑菌活性，浓度为4000 μmol·L^-1时，对ECV304细胞的抑制率分别为84.22%和65.56%，对大肠杆菌、绿脓杆菌和金黄色葡萄球菌均显示抑菌活性，具有较好的荧光特性，可用于细胞染色及荧光标记。     

新型香豆素类衍生物的合成及其抗菌活性

以水杨醛及其衍生物为原料,通过缩合、水解、酰化、酯化四步反应合成了4个新的香豆素类衍生物-取代香豆素-3-酰水杨酸(4a～4d),其结构经uv,1H NMR,IR和元素分析表征.初步抗菌活性测试结果表明,4a-4d均有一定程度的抗真菌活性.     

Dually Activated Organo- and Nano-cocatalyzed Synthesis of Coumarin Derivatives

A wide range of substituted coumarin derivatives were synthesized by refluxing in acetonitrile, ethyl acetoacetate, and ethyl benzoyl acetate with a wide range of structurally diverse phenol derivatives within a short reaction time with a catalytic combination of pyridine dicarboxylic acid as organocatalyst and nanocrystalline ZnO.     

香豆素基Schiff碱类化合物的合成及抗氧化性能

以2,3,4-三甲氧基苯甲醛为原料,经脱甲基、Knoevenagel缩合、亲核加成等反应合成了2个香豆素基Schiff碱类化合物,其结构经核磁共振谱(¹H NMR))和质谱(MS)确证。 并采用淬灭二苯代苦味肼基自由基(DPPH)、2,2'-联氮双(3-乙基苯并噻唑啉-6-磺酸)二铵盐(ABTS)和羟自由基等方法对其体外抗氧化性能进行了表征。 结果表明,目标化合物对3种自由基均具有一定的淬灭活性,其中对DPPH和羟自由基的淬灭活性高于母体化合物7,8-二甲氧基-3-氨基香豆素,具有较高的抗氧化活性。     

3-二茂铁基二氢吡唑衍生物的合成及晶体结构

以乙酰基二茂铁为原料合成了6种二茂铁取代的4,5-二氢吡唑化合物,用IR、MS、1H NMR测试技术对其结构进行了表征,并采用X射线衍射方法测定了化合物2b的晶体和分子结构。C30H26Fe2N2O(化合物2b)属于三斜晶系,空间群P1,晶胞参数：a=0.9275(4) nm,b=1.1327(5) nm,c=1.1912(5) nm,α=88.67(2)°,β=79.925(18)°,γ=70.345(18)°,V=1.1595(9) nm3,Z=2,F(000)=560,Dc=1.553 g/cm3,μ=1.279 mm-1,R1=0.0351,wR2=0.0934。     

Synthesis of Coumarin Derivatives as Inhibitors of Platelet Aggregation

In a search for the inhibitors of platelet aggregation, certain coumarin derivatives were synthesized and evaluated for antiplatelet activity against thrombin(Thr)-, arachidonic acid(AA)-, collagen(Col)-, and platelet-activating-factor(PAF)-induced aggregation in washed rabbit platelets. These compounds were synthesized from 4-hydroxycoumarin ( 1 ) or naphthalen-1-ol via alkylation and Reformatsky-type condensation (Schemes 1–3). Among them, 4-[(2,3,4,5-tetrahydro-4-methylidene-5-oxo-2-phenylfuran-2-yl)methoxy]-2H-1-benzopyran-2-one ( 6b ) showed potent antiplatelet effects on AA- and PAF-induced aggregation with IC₅₀ values of 8.21 and 103.67 m?M , respectively (see Tables 1 and 2). The antiplatelet potency of 6b against PAF-induced aggregation could be further improved by introducing a proper substituent at the 2-phenyl group of the lactone ring.     

Synthesis and Antibacterial Evaluation of Novel 3,6-Disubstituted Coumarin Derivatives

A novel series of 3,6-disubstituted coumarin derivatives were synthesized by the reaction of ethyl-2-(3-acetyl-2-oxo-2H-chromen-6-yl)-4-methylthiazole-5-carboxylate with thiosemicarbazide and various phenacyl bromides / 3-(2-bromoacetyl)-2H-chromen-2-ones / 2-(2-bromoacetyl)-3H-benzo[f]chromen-3-one in ethanol having catalytic amount of acetic acid under reflux conditions with good yields. All the synthesized compounds were fully characterized by spectral studies and evaluated for their in vitro antibacterial activity against Pseudomonas aeruginosa, Bacillus subtilis (Gram positive), Escherichia coli, and Azatobacter (Gram negative) bacterial strains. Activity results revealed that the compound 6h against Escherichia coli and compound 6i against Pseudomonas aeruginosa and Escherichia coli have shown maximum zones of inhibition. Remaining compounds showed moderate to good activity against all the tested bacterial strains compared with the standard drug cefotaxime.     

香豆素单取代蔗糖衍生物的合成及其荧光性能

以7-羟基-4-甲基香豆素为原料制得两个香豆素衍生物(2a和2b);2与蔗糖反应合成了两个新型的香豆素单取代蔗糖衍生物(3a和3b),其结构经1H NMR,IR和LC-MS表征.3a和3b均具有较强的荧光强度,且荧光强度对pH的变化较为敏感,可选择性地识别Fe3+.     

Synthesis and Cytotoxic Activity of Coumarin Derivatives Containing Benzotriazole Moieties

Three coumarin derivatives containing benzotriazole moieties, 3-(1-benzotriazolyl)-4-methyl-coumarin (BMC), 3-(1-benzotriazolyl)-4-methyl-benzo[7,8]coumarin (BMBC), and 3-(4-methyl-1-benzotriazolyl)-4-methyl-benzo[7,8]coumarin (MBMBC), were synthesized. Among them, 3-(4-methyl-1-benzotriazolyl)-4-methyl-benzo[7,8]coumarin has been structurally characterized by X-ray crystallography. The cytotoxic effect by Sulforhodamine B (SRB) assay with these compounds against the human hepatocellular carcinoma cell lines (HepG-2) was carried out in vitro. The preliminary results showed that all compounds inhibit HepG-2 growth effectively.     

新型香豆素衍生物的设计、合成及除草活性研究

以(未)取代的间苯二酚与β-酮酸酯类化合物为起始原料,在酸的催化下发生Pechmann 反应,合成了4个关键中间体--7-羟基香豆素衍生物(1a~1d),其与芳氧乙(丙)酰氯作用,合成了8个结构新颖的7-芳氧乙酰氧基香豆素衍生物(2a~2h),其结构经¹H NMR、¹³C NMR和元素分析表征。油菜平皿法和稗草小杯法的测试结果表明,目标化合物对双子叶植物油菜根长的抑制效果好,与阳性对照药2,4-D相当,并表现出一定的构效关系。进一步的温室盆栽实验(50 g/亩)表明,茎叶处理时,部分目标化合物(如2a~2e)对双子叶植物的抑制率为100%,与2,4-D的防效相当,具有作为先导化合物进一步优化的价值。      

4-苯氨基喹唑啉类衍生物的合成、表征及晶体结构

以香草醛为原料,经过7个步骤合成得到了12个新的4-苯氨基喹唑啉类化合物8a～81,产物的结构经1H NMR,13C NMR,IR,MS和元素分析确认,并用X射线衍射法测定化合物8b的晶体结构.化合物8b属三斜晶系,P-l空间群,晶胞参数:α=0.8868(5)nm,b=1.0239(6)nm,c=1.4515(9)nm,α=71.02(2)°,β=82.42(2)°,γ=71.78(2)°,V=1.1831 um3,Z=2,Dc=1.430Mg/m3,μ(MoKα)=1.773mm-1,λ=0.071073nm,F(000)=522.     

含氟香豆素透明质酸衍生物的合成及其荧光性能

以间氨基苯酚与三氟乙酰乙酸乙酯反应生成4-三氟甲基-7-氨基香豆素,其与氯乙酰氯反应生成-4-三-氟甲基-7-氯乙酰氨基香豆素。 该化合物与透明质酸钠反应得到了含氟香豆素透明质酸衍生物。 利用荧光光谱等分析技术研究了浓度、pH值和温度变化对该透明质酸衍生物荧光强度的影响,同时研究了金属离子对其荧光强度的影响。 结果表明,一定浓度范围内,荧光强度随透明质酸衍生物浓度增大而逐渐增强;在pH值为3.86～8.85范围内,其荧光强度较为稳定;在10～80 ℃范围内,其荧光强度随温度的升高而逐渐减弱;在常见干扰离子存在下,Fe3+对其荧光强度有较为显著的影响,其荧光强度显著降低。 这为探索透明质酸在生命机体内的药物载体机理及其靶向作用提供良好的实验基础。     

L-7-羟基香豆素氨基酸衍生物的合成及其性能

以保护L-谷氨酸（2）为原料,与N,N′-羰基二咪唑反应制得化合物3; 3与丙二酸单乙酯镁盐反应制得β-酮酯（4）; 4分别与4-氟间苯二酚和4-氯间苯二酚进行Pechmann缩合后,在酸中脱除保护基合成了L-7-羟基香豆素氨基酸（1a）及其两个衍生物（1b, 35.3%和1c, 40.6%）,其结构经¹H NMR, ¹³C NMR和HR-MS(ESI)确证。采用UV-Vis研究了1b和1c的pKa。结果表明：1b和1c的pKa分别为6.21和6.14。两个衍生物的荧光性能与pH密切相关。     

Synthesis of Coumarin Substituted Triazolothiadiazine Derivatives via Ring Transformation Reaction

A novel ring transformation reaction for the synthesis of 3‐(3‐aryl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl)‐2H‐chromen‐2‐ones has been described. Reaction of 3‐(2‐bromoacetyl)coumarins ( 1 ) with 5‐aryl‐1,3,4‐oxadiazole‐2‐thiol ( 2 ) gave ketones ( 4a–h ). The in situ formed ketones ( 4a–h ) were reacted with hydrazine hydrate to give 3‐(3‐aryl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl)‐2H‐chromen‐2‐ones ( 3a–h ) and not 5 or 6 . The compounds ( 3a–h ) can also be prepared by the reaction of 3‐(2‐bromoacetyl)coumarins ( 1 ) with 5‐aryl‐1,3,4‐oxadiazole‐2‐thiol ( 2 ) in anhydrous ethanol to give corresponding 3‐(2‐(5‐aryl‐1,3,4‐oxadiazol‐2‐ylthio)acetyl)‐2H‐chromen‐2‐ones ( 4a–h ). These on reaction with hydrazine hydrate in acetic acid gave corresponding 3‐(3‐aryl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl)‐2H‐chromen‐2‐ones ( 3a–h ).