吡喃并[3,2-c]吡啶-5-酮衍生物与血清白蛋白相互作用的光谱和分子对接研究

通过荧光光谱和紫外-可见吸收光谱法,在模拟生理条件下,研究了吡喃并[3,2-c]吡啶-5-酮衍生物-2-氨基-7-甲基-3-氰基-4-(4-甲苯)-吡喃并[3,2-c]吡啶-5-酮(AMP)与牛血清白蛋白(BSA)的相互作用。探讨了AMP对BSA的荧光猝灭过程的猝灭机理。不同温度下的Stern-Volmer曲线和紫外-可见吸收光谱表明:该衍生物主要以静态猝灭的方式使牛血清白蛋白的荧光猝灭。热力学参数表明两者之间的作用力类型主要为疏水作用力。用同步荧光技术考察了这一衍生物对牛血清白蛋白构象的影响。分子对接表明,该衍生物可能位于白蛋白的疏水腔IIA处。     

微波辐射下吡喃并[3,2-c]吡啶酮和吡喃并[4,3-b]吡喃酮类化合物的高效绿色合成

对离子液体介质中微波辐射下芳香醛、吡啶(喃)酮和丙二腈的三组分缩合反应的研究发现,该反应可快速完成,无需使用催化剂,并以较高的收率生成相应的吡喃并[3,2-c]吡啶酮和吡喃并[4,3-b]吡喃酮类化合物。与文献方法相比,该方法具有反应速度快、效率高、原料易得、对环境友好等优点。另外,该方法已成功地应用于吡喃并[3,2-c]吡啶酮和吡喃并[4,3-b]吡喃酮-嘧啶核苷杂化体的合成中。     

1,4-二氢吡喃类化合物与牛血清白蛋白相互作用的研究

用荧光光谱法研究了人体生理pH条件下,3-甲基-6-氨基-5-氰基-4-(2-邻羟基苯基)-1-苯基-1,4-二氢吡喃并[2,3-c]吡唑(I)与牛血清白蛋白(BSA)间的结合反应。获得了不同温度下I与BSA作用的结合常数K和结合位点数n,计算给体-受体间距离r为5.75 nm及能量转移效率E为0.74。证实了I与BSA的相互结合作用为单一的静态猝灭过程,结合力以疏水作用力为主。     

香豆素并[4,3-b]吡喃-4-酮类衍生物的有效合成方法

在哌啶和聚乙二醇-400的作用下,通过3-乙酰基-4-羟基香豆素与芳香醛的缩合反应,合成了3-肉桂酰基-4-羟基香豆素,接着在I2-DMSO氧化体系下,成功制备了一系列香豆素并[4,3-b]吡喃-4-酮衍生物.该反应操作简单、条件温和、收率良好.产物结构经NMR,IR,MS及元素分析数据得以证实.     

吡喃并[3,2-c]吡啶酮-嘧啶核苷杂化体与白蛋白相互作用的光谱和分子模拟研究

在模拟生理条件下,用荧光、紫外吸收光谱法及分子模拟研究了具有抗病毒活性的吡喃并[3,2-c]吡啶酮-嘧啶核苷杂化体-3 ′,5 ′-二-O-乙酰基-5-[2-氨基-7-甲基-5-氧代-5,6-二氢-4H-吡喃并[3,2-c]吡啶-3-氰基]-2 ′-脱氧尿苷(PPNH)与牛血清白蛋白( BSA)的相互作用.PPNH对牛...     

有机催化不对称[3+3]环化合成新型光学活性稠合多环3,4-二氢吡喃并[4,3-b]吡喃-5-(2H)-酮（英文）

发展了一种手性双功能方酰胺催化的4-羟基-2(H)-吡喃并[2',3':4,5]吡喃并[2,3-c]吡唑-2,5(7H)-二酮与(E)-2-硝基烯丙基醋酸酯之间的对映选择[3+3]环化反应,为立体选择构筑稠合多环3,4-二氢吡喃并[4,3-b]吡喃-5-(2H)-酮骨架提供了途径.在衍生自(1R,2R)-1,2-二苯基乙-1,2-二胺的手性双功能方酰胺的催化下,以中等至较高产率、高的反式选择性和中等至优秀的对映选择性得到了一系列具有两个连续手性中心的新型稠合多环3,4-二氢吡喃并[4,3-b]吡喃-5-(2H)-酮衍生物.     

新型芳并吡喃类多环化合物的合成与光谱性质研究

本文设计并经由分子内碳-碳偶联反应合成了一系列基于芳并吡喃供电子功能片段的有机功能小分子,包括萘并[2,1-b：6,5-b’]二苯并吡喃4a,萘并[2,1-b：6,5-b’]二萘并吡喃4b,萘并[2,1-b：6,5-b’]二[2-（5-己基噻吩基）]苯并吡喃4c。通过紫外光谱和荧光光谱研究表明,这类化合物在370~400 nm波长范围内具有最大紫外吸收,在417~462 nm波长范围内具有最大荧光发射。说明随着共轭平面的增大或共轭链长度的增加,化合物的吸收和荧光光谱均发生显著的红移,是一类具有丰富光电活性的有机功能分子。     

微波辐射下一步合成吡啶和吡喃衍生物

吡啶衍生物具有重要的生物活性 ,用作药物和农用化学品如ｈｅｒｂｉｃｉｄｅｓ[1 ] 。有些吡啶衍生物具有荧光性质 ,已被用于液晶工业。一些 2 氨基 4Ｈ吡喃具有光化学活性[2 ] 。多取代的四氢吡喃还是许多天然产物的基本结构单元[3] 。 4 芳基四氢吡喃可以转变成吡啶衍生物 ,后者是药物上重要的钙离子通道调节剂[4～6] 。自从ＳａｋｕｒａｉａｎｄＭｉｄｏｒｉｋａｗａ[7] 于 1 968年第一次报道在醋酸铵存在下丙二腈与α、β 不饱和酮反应得到吡啶衍生物以来 ,丙二腈与α、β 不饱和酮反应用于吡啶和吡喃衍生物的合成已愈来愈引起人们兴趣…     

色烯并[4,3-d]吡唑并[3,4-b]吡啶衍生物的三组分合成及荧光性质研究

在三乙胺催化下,利用取代水杨醛、氰乙酸酯和5-氨基吡唑的三组分反应合成了一系列5-氨基色烯并[4,3-d]吡唑并[3,4-b]吡啶-6(3H)-酮衍生物4a～4v.荧光研究表明部分合成得到的化合物具有高的荧光量子产率.     

荧光光谱法研究一种噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物与牛血清白蛋白的相互作用

用荧光光谱法研究了在生理条件下,3-对氯苯基-2-(4-叔丁基苯氧基)-3’-氧环己烷并噻吩并[2,3-d]嘧啶-4(3H)-酮(PTP)与牛血清白蛋白(BSA)的相互作用。实验表明,PTP主要以静态猝灭方式使BSA荧光强度显著降低。计算了不同温度下二者的结合常数和结合位点数,并根据热力学参数确定了PTP与BSA之间的作用力主要为氢键或范德华力。根据Frster非辐射能量转移机理,测定了PTP与BSA相互结合时的作用距离,并用同步荧光技术讨论了其衍生物对BSA构象的影响。     

二氧化硫脲:一锅合成吡喃并[4,3-b] 吡喃类化合物的高效可重复使用有机催化剂（英文）简

A series of pyrano[4,3-b]pyran derivatives have been synthesized in excellent yields by the reaction of aromatic aldehydes with malononitrile or cyanoacetate and 4-hydroxy-6-methylpyran-2-one in water at 80℃, with the transformation being catalyzed by an aqueous solution of thiourea dioxide (TUD). Upon completion of the reaction, the product was isolated by filtration or extraction and the remaining aqueous TUD solution could be reused several times without any discernible impact on its catalytic activity. This procedure offers several advantages over existing procedures, including high yields, operational simplicity, the use of a non-toxic catalyst and solvent, short reaction time and minimum pollution of the environment, making it a useful and attractive process for the preparation of pyrano[4,3-b]pyran derivatives.     

4-(Succinimido)-1-butane sulfonic acid as a Bronsted acid catalyst for synthesis of pyrano[4,3-b]pyran derivatives under solvent-free conditions

4-(Succinimido)-1-butane sulfonic acid as an efficient and reusable Bronsted acid catalyzed the synthesis of pyrano[4,3-b]pyran derivatives under solvent-free conditions.The catalyst can be prepared by mixing succinimide and 1,4-butanesultone that is more simple and safer than the preparation of succinimide sulfonic acid.This method has the advantages of high yield,clean reaction,simple methodology and short reaction time.The catalyst could be recycled without significant loss of activity.     

Sequential approach to the synthesis of 'U and Z' shaped polycyclic heteroarenes

The synthesis of three new classes of heteroarenes, built through the sequential fusion of naphthalene, benzo/naphtho[b]oxepine and thiochromene rings with pyran and pyrimidine ring systems to give 'U and Z' shaped structural frameworks is reported. The methodology is based on the synthesis of pyran fused intermediates, 1-methylthio-3-oxo-5,6-dihydro-3H-benzo[f]chromene-2-carbonitrile (3), 4-methylthio-2-oxo-5,6-dihydro-2H-benzo/naphtho[b]pyrano[2,3-d]oxepine-3-carbonitriles (10, 20) and 4-methylthio-2-oxo-2,5-dihydrothiochromeno[4,3-b]pyran-3-carbonitriles (15) from the reaction of 2-tetralone, benzo/naphtho[b]oxepin-5-ones and thiochromen-4-ones with methyl 2-cyano-3,3-dimethylthioacrylate respectively. Further condensation of intermediates 3, 10, 20 and 15 with amidines led to the formation of tetracyclic 'U' shaped 4-amino-2-aryl-7,8-dihydro-5-oxo-5H-naphtho[2,1-b]pyrimido[4,5-d]pyrans (8) and 'Z' shaped 4-amino-2-aryl-5-oxo-12,13-dihydro-5H-benzo/naphtho[b]oxepino[5,4-b]pyrimido[4,5-d]pyrans (12, 22) and 4-amino-2-aryl-5-oxo-5,12-dihydrothiochromeno[4,3-b]pyrimido[4,5-d]pyrans (17). Compound 12f forms a chain of dimers through N-HO interactions as indicated by the X-ray structure analysis, and the quantum chemical calculations performed at the MP2 level indicate that this interaction energy is 10 kJ mol(-1).     

加热与超声辐照条件下4-(丁二酰亚胺基)-1-丁烷磺酸Brnsted酸催化剂催化吡喃并[4,3-b]吡喃衍生物合成(英文)

4-(Succinimido)-1-butane sulfonic acid was shown to be an efficient and reusable Brnsted acid catalyst for the synthesis of pyrano[4,3-b]pyran derivatives using thermal and ultrasonic conditions. The catalyst was prepared by mixing succinimide and 1,4-butanesultone, which is simpler and safer than the preparation of succinimide sulfonic acid. This method has the advantages of high yield, clean reaction, simple methodology, and short reaction time. The catalyst can be recycled without loss of activity.     

4-(Succinimido)-1-butane sulfonic acid as a Brönsted acid catalyst for synthesis of pyrano[4,3-b]pyran derivatives under solvent-free conditions

4-(Succinimido)-1-butane sulfonic acid as an efficient and reusable Brönsted acid catalyzed the synthesis of pyrano[4,3-b]pyran derivatives under solvent-free conditions. The catalyst can be prepared by mixing succinimide and 1,4-butanesultone that is more simple and safer than the preparation of succinimide sulfonic acid. This method has the advantages of high yield, clean reaction, simple methodology and short reaction time. The catalyst could be recycled without significant loss of activity.     

Synthesis of a novel bifunctional oxyammonium-based ionic liquid: Application for the synthesis of pyrano[4,3-b]pyrans and tetrahydrobenzo[b]pyrans

In the present investigation, a novel bifunctional oxyammonium-based ionic liquid, namely, 2,2′-(ethane-1,2-diylbis[oxy])bis(ethan-1-aminium)-2,2,2-trifluoroacetate, was designed and synthesized. The structure of the titled ionic liquid was characterized using Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (¹HNMR), carbon nuclear magnetic resonance (¹³CNMR), fluorine nuclear magnetic resonance (¹⁹FNMR), homonuclear COSY nuclear magnetic resonance (NMR), thermogravimetry (TG), derivative thermogravimetry (DTG) analysis, X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The described ionic liquid demonstrated robust catalytic performance in the synthesis of pyrano[4,3-b]pyrans and tetrahydrobenzo[b]pyran derivatives. The ionic liquid presents a high potential of recycling and reusing capability in both types of model reactions.     

Synthesis of New Fused Derivatives of 4-(Fur-2-yl)pyrano[4,3-b]pyridines

Russian Journal of General Chemistry - A method for the synthesis of new fused derivatives of 4-(fur-2-yl)pyrano[4,3-b]pyridines was developed by hydrolysis of...     

Fused Heterocyclic Systems Derived from 2,6-Diaryl-3,5-dibenzylidenetetrahydro-4H-thiopyran-4-ones

The reaction of 2,6-diphenyl and 2,6-di-p-tolyltetrahydro-4H-thiopyran-4-ones with benzaldehyde afforded 2,6-diphenyl and 2,6-di-p-tolyl-3,5-dibenzy-lidenetetrahydro-4H-thiopyran-4-ones, which, on treatment with hydroxylamine hydrochloride, hydrazine hydrate and thiourea, gave thiopyrano[4,3-c]isoxazole, thiopyrano[4,3-c]pyrazole and thiopyrano[4,3-d]pyrimidine derivatives, respectively. Also, the reaction of dibenzylidenetetrahydrothiopyran-4-ones with malononitrile in piperidine and malononitrile in ammonim acetate afforded thiopyrano[4,3-b]pyran and thiopyrano[4,3-b]pyridine derivatives, respectively, while treatment with ethyl acetoacetate gave acetyl thiopyrano[4,3-b]pyran derivatives. On the other hand, treatment of 2,6-diphenyl and 2,6-di-p-tolyltetrahydro-4H-thiopyran-4-ones with elemental sulfur and malononitrile in the presence of diethylamine gave thieno[2,3-c]thiopyran derivatives. Structures of all compounds were confirmed from their spectral and analytical data.     

Synthesis of New Fused Furo- and Thienopyridines

Russian Journal of General Chemistry - A method was developed for the synthesis of new fused derivatives of pyrano[4,3-b]thieno(furo)-pyridine, namely...     

Synthesis of a 4H-anthra[1,2-b]pyran derivative and its antimicrobial activity

The five-step synthesis of the new 4H-anthra[1,2-b]pyran derivative 1 is reported. The key steps in this approach included a Marschalk alkylation of 1,4-dihydroxyanthraquinone followed by a Baker-Venkataraman reaction and then an acid-catalyzed cyclization of ring A to form the 4H-anthra[1,2-b]pyran system. Two compounds, the 4H-anthra[1,2-b]pyran 1 and the anthraquinone derivative 6 were evaluated for antimicrobial activity and showed moderate antialgal, antifungal, and antibacterial activities.