1,3,4-(噁)二唑类化合物杀菌活性研究进展

1,3,4-二唑类化合物因其独特的生物活性在农药、医药等领域受到广泛关注.将1,3,4-二唑环引入不同的化合物结构中,通过结构修饰能生成一系列具有广谱生物活性的化合物.它在新型农药创制中发挥越来越重要的作用.按照不同的结构进行分类,从杀菌方面对1,3,4-二唑类化合物的生物活性研究进展进行了综述,重点介绍了该类化合物的一些生物活性研究方面的工作,并对它的发展趋势和应用前景作了展望.     

Biological Activity,Lipophilicity and Cytotoxicity of Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines

Antibiotic resistance is now a global problem, and the lack of effective antimicrobial agents for the treatment of diseases caused by resistant microbes is increasing. The 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines presented in this article may provide a good starting point for the development of potential new effective antimicrobial agents useful in the treatment of bacterial and fungal infections. Particular attention is drawn to the 1,3,4-oxadiazole derivative marked with the number 29 with 5-nitrofuran-2-yl substituent in its chemical structure. This substance showed a strong bactericidal effect, especially against Staphylococcus spp., and no cytotoxicity to the L929 normal cell line.     

In Vitro and In Silico Evaluation of New 1,3,4-Oxadiazole Derivatives of Pyrrolo[3,4-d]pyridazinone as Promising Cyclooxygenase Inhibitors

Since long-term use of classic NSAIDs can cause severe side effects related mainly to the gastroduodenal tract, discovery of novel cyclooxygenase inhibitors with a safe gastric profile still remains a crucial challenge. Based on the most recent literature data and previous own studies, we decided to modify the structure of already reported 1,3,4-oxadiazole based derivatives of pyrrolo[3,4-d]pyridazinone in order to obtain effective COX inhibitors. Herein we present the synthesis, biological evaluation and molecular docking studies of 12 novel compounds with disubstituted arylpiperazine pharmacophore linked in a different way with 1,3,4-oxadiazole ring. None of the obtained molecules show cytotoxicity on NHDF and THP-1 cell lines and, therefore, all were qualified for further investigation. In vitro cyclooxygenase inhibition assay revealed almost equal activity of new derivatives towards both COX-1 and COX-2 isoenzymes. Moreover, all compounds inhibit COX-2 isoform better than Meloxicam which was used as reference. Anti-inflammatory activity was confirmed in biological assays according to which title molecules are able to reduce induced inflammation within cells. Molecular docking studies were performed to describe the binding mode of new structures to cyclooxygenase. Investigated derivatives take place in the active site of COX, very similar to Meloxicam. For some compounds, promising druglikeness was calculated using in silico predictions.     

2-(4-氨基苯基)-5-(2-烷氧基苯基)-1,3,4-(噁)二唑的合成及表征

以对硝基苯甲酸和水杨酸甲酯为起始原料合成了两种新的1,3,4-噁二唑类化合物——2-(4-氨基苯基)-5-(2-乙氧基苯基)-1,3,4-噁二唑和2-(4-氨基苯基)-5-(2-戊氧基苯基)-1,3,4-噁二唑。合成过程中,1,3,4-噁二唑化合物上的硝基采用钯碳催化氢化的方法还原成氨基,使后处理变得容易,产率显著提高,分别达98.4%和96%。通过IR和1HNMR确证了相关化合物的结构。     

含1,3,4-(噁)二唑环的有机电致发蓝光材料及器件研究进展

1,3,4–口恶 二唑环是一个具有高电子亲和势和空穴阻挡作用的基团,含该基团的化合物是一类具有良好电子传输功能的有机电致发光材料。近年来含1,3,4–口恶 二唑环化合物发蓝光的有机电致发光材料已成为材料科学研究的一个热点。综述了含1,3,4–口恶 二唑环的小分子和高分子发蓝光的有机电致发光材料的分子结构、性能及其器件性能的研究现状,并对提高这类材料性能的分子设计方面作了简要的展望。     

新型熊果酸喹啉衍生物抗肿瘤活性研究

原料为五环三萜类天然产物熊果酸,合成新型熊果酸喹啉衍生物。使用元素分析法、ESIMS、13C NMR等,分析1,3,4-噁二唑衍生物4a-4f,以及熊果酸喹啉酰肼衍生物3a-3f。采用MTT法,对4a-4f、3a-3f进行测试,分析对三种肿瘤细胞株的增殖抑制活性。结果显示,对三种肿瘤细胞株,包括SMMC-77213、HeL、MDA-MB-231,3a-3c都有明显的抑制活性。比对照依托泊苷更强,对SMMC-77213、HeL、MDA-MB-231的IC50值,分别是17.49～19.43μmol/L、0.84～1.19μμmol/L、1.17～1.85μμmol/L。根据抗肿瘤活性结果显示,喹啉基引入熊果酸分子中,羧基修饰为1,3,4-噁二唑基、酰肼基,抗肿瘤活性能够明显增强,酰肼的衍生物为侧链,相比噁二唑的衍生物活性更佳。因此,能够进一步优化熊果酸结构,提升抗肿瘤活性。     

Synthesis and anti-inflammatory activity of some novel 1,3,4-oxadiazole derivatives

Some novel 1,3,4-oxadiazoline and 1,3,4-oxadiazole derivatives have been synthesized from 3-hydroxy-5,6-diphenyl-1,2,4-triazine. Illucidation of the structures of the isolated products has been proved in the light of their elemental analysis, spectroscopic data and unambiguous synthesis in certain cases. Some derivatives have shown promising anti-inflammatory activity in comparison to phenylbutazone.     

1，3，4-噁二唑类化合物合成及应用的研究新进展

1,3,4-噁二唑类化合物因具有独特的生物活性和光学活性而被广泛研究,该类化合物在农药、医药、材料等领域有广泛应用。将1,3,4-噁二唑环引入不同的化合物结构中,通过结构修饰能生成一系列具有广谱生物活性的化合物及电致发光材料。因此,1,3,4-噁二唑衍生物的合成也成了人们研究的热点。文章综述了近年来合成1,3,4-噁二唑类化合物的传统方法、微波辅助合成法、固相合成法,对其在医药、材料等方面的应用进行了总结,并对其发展趋势和应用前景作了展望。     

Preparation and characterization of ordered thin films based on aromatic poly(1,3,4-oxadiazole)s

Ultrathin layers of aromatic polyoxadiazoles by using the Langmuir-Blodgett technique are prepared for the first time. The syntheses and characterization of new soluble aromatic poly(1,3,4-oxadiazole)s are described. The polyoxadiazoles contain tetraphenyl silane units in the main chain or pendent alkylamido groups. Both the precursor route via polyhydrazide followed by thermal cyclization in bulk, and the direct spreading of poly(1,3,4-oxadiazole)s are used for film forming. The supramolecular structures of all ordered poly(arylene-1,3,4-oxadiazole) LB films are characterized by FTIR spectroscopy, X-ray scattering and atomic force microscopy, respectively.     

1,3,4-噁二唑类液晶化合物研究进展

介绍了近年来1,3,4-噁二唑类液晶研究进展,包括线型、星型1,3,4-噁二唑类液晶及带1,3,4-噁二唑基团的聚合物液晶。介绍了这类化合物结构与液晶性能及光电性能间的关系,所有的研究表明这类物质在制备光电器件方面具有广泛的应用前景。     

2-对溴苯基-5-芳基-1,3,4噁二唑类化合物的合成研究

设计并合成了3个2-对溴苯基-5-芳基-1,3,4-噁二唑类化合物,它们是进一步合成具有光电功能特性的噁二唑类化合物的重要前体。探讨了不同的合成条件和途径,发现以P(Ph)3/(Et)3N/CCl4作为脱水剂来合成非对称的1,3,4-噁二唑是较好的合成方法。     

1,3,4-噻二唑类液晶化合物的研究进展

综述了近年来1,3,4-噻二唑类液晶化合物的研究进展,该类化合物形成棒状液晶、楔形液晶、弓形液晶、Polycatenar液晶、盘状液晶的分子结构及其自组装形成的液晶相结构。介绍了分子中末端基团、烷基链数目、刚性核长度等结构常数对液晶自组装结构的的影响。与含氧的杂环类似物1,3,4-噁二唑液晶化合物相比,1,3,4-噻二唑类液晶化合物的液晶性、光电性等更加优越。液晶方面类比表明,它具有更好的液晶性质。     

Synthesis of Ecofriendly Functionalized Oxadiazole,Imidazole, Triazole and Pyridine Derivatives

5-Pentadecyl-1,3,4-oxadiazol-2-amine (2) was employed as key intermediate for the synthesis of some new functionalized five and six membered heterocyclic derivatives. The synthesized compounds were reacted with propylene oxide to obtain surface active agents having good surface activity, high solubility in water and good biodegradability. Moreover, the functionalized surfactants showed good antimicrobial activity against gram negative and gram positive organisms. The new compounds are easily synthesized, economical and environmentally friendly and are expected to constitute an important class of organic compounds for medicinal purposes in the future.     

含噁二唑类有机电致发光材料的研究进展

有机电致发光器件(OLED)具有视角宽、功耗低、响应速度快、发光亮度和发光效率高、能实现全色显示等优点,备受科学界和产业界的广泛重视。特别是自从1987年Tang首次报道了工作电压低、发光亮度高的OLED以来,其研究工作取得了更快速地发展。近十余年里,已经逐渐成为多学科交叉的具有高技术含量的前沿课题。含1,3,4-噁二唑环的-聚合物作为一种新型的具有电子传输功能的有机电致发光材料在近10年的研究中引起了人们的极大关注。由于1,3,4-噁二唑环是一个具有高电子亲和势和空穴阻挡作用的基团,因此含该基团的化合物是一类具有良好电子传输功能的有机电致发光材。     

The synthesis,optical properties and x-ray crystal structure of novel 1,3,4-oxadiazole derivatives carrying a thiophene unit

Novel, 1,3,4-oxadiazole derivatives carrying a thiophene unit were synthezised and their structures confirmed by elemental analysis, FT-IR and ¹H NMR. UV–vis absorption and photoluminescence spectroscopy revealed emission peaks located between 427 and 437 nm; the measured absorption λ_max and emission λ_em reflected the electron-donor character of the 1,3,4-oxadiazole derivatives. The crystal structure of one of the compounds was investigated.     

1,3,4-噁二唑硫醚及(亚)砜类化合物的生物活性研究进展

按照生物活性的类别进行分类,综述了国内外近年来有关1,3,4-噁二唑硫醚及(亚)砜类化合物的生理活性研究进展,展望了其发展趋势及应用前景。     

Fatty Acids in Heterocyclic Synthesis. Part XIV: Synthesis of Surface Active Agents from Some Novel Class of Oxadiazole,Thiadiazole and Triazole Derivatives Having Microbiological Activities

Reaction of stearic acid with semicarbazide in refluxing POCl₃ afforded 2-amino-5-heptadecyl 1,3,4-oxadiazole. Acylation of the amino group with acetic anhydride, ethyl chloroacetate and chloroacetic acid gave amide and β-amino acid derivatives. These compounds were cyclized to imidazo[2,1-b]oxadiazole derivatives by two different techniques. Treating the starting oxadiazole compound with P₂S₅, hydroxyl amine and hydrazine hydrate in benzene afforded thiadiazole and triazole derivatives. Unexpectedly, triazolo[3,4-b][1,3,4]oxadiazole derivative was obtained when 1,3,4-oxadiazole derivative was refluxed with hydrazine hydrate in ethanol. The biological activities of the synthesized compounds were screened in vitro against some gram positive and gram negative bacteria and fungi. Addition of quantitative amount of propylene oxide units (3, 5, 7 mol) to the synthesized compounds afforded new nonionic surfactants. The physico-chemical and surface properties of the novel synthesized surfactants such as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. In addition, surface parameters including effectiveness (π _CMC), efficiency (PC₂₀), maximum surface excess (Γ_max) and (A _min) were examined.     

Synthesis and characterization of a new oxadiazole-functionalized maleic anhydride-N-vinylpyrrolidone copolymer and its application in CaCO3 based microparticles

A new polymer–drug conjugate based on poly(N-vinylpyrrolidone-co-maleic anhydride) as support and 2-amino-5-(4-methoxy-phenyl)-1,3,4-oxadiazole, having antimicrobial and antifungal activity, was synthesized by Higashi–Yamazaki reaction. The functionalized copolymer having a substitution degree of 29% was fully characterized in terms of chemical structure by ¹H NMR, FTIR and UV–Vis spectroscopy, and by molecular weight measurements. The crystallization of CaCO₃ particles from saturate aqueous solutions in the presence of the newly synthesized conjugate copolymer, comparative with particles prepared in similar conditions but without polymer, has been investigated. The obtained particles were characterized by scanning electron and polarized optical microscopy, X-ray diffraction, particles charge density, and electrophoresis. These new composite materials are excellent candidates for use in biomedical applications, particularly for drug delivery.     

New fluorinated poly(1,3,4-oxadiazole-ether-imide)s

New fluorinated poly(1,3,4-oxadiazole-ether-imide)s have been prepared by solution polycondensation reaction of different aromatic diamines having preformed 1,3,4-oxadiazole ring, such as 2,5-bis(p-aminophenyl)-1,3,4-oxadiazole, 2,5-bis[p-(4-aminophenoxy)phenyl]-1,3,4-oxadiazole, 2,5-bis[p-(3-aminophenoxy)phenyl]-1,3,4-oxadiazole, 2-(4-dimethylaminophenyl)-5-(3,5-diaminophenyl)-1,3,4-oxadiazole and 2-(4-fluorophenyl)-5-(3,5-diaminophenyl)-1,3,4-oxadiazole, with an aromatic dianhydride incorporating ether linkages and hexafluoroisopropylidene group, namely 1,1,1,3,3,3-hexafluoro-2,2-bis-[(3,4-dicarboxyphenoxy)phenyl]-propane dianhydride. The polymers were easily soluble in polar organic solvents, such as N-methylpyrrolidinone, N,N-dimethylformamide, and pyridine, as well as in certain low boiling-point organic solvents, such as tetrahydrofuran and chloroform. Very thin coatings deposited onto silicon wafers exhibited smooth, pinhole-free surface in atomic force microscopy. The polymers showed high thermal stability with decomposition temperature being above 410 °C. They exhibited a glass transition in the temperature range of 183-217 °C, with reasonable interval between glass transition and decomposition temperature. Solutions of some polymers in N,N-dimethylformamide exhibited blue fluorescence, having maximum emission wavelength in the range of 411-424 nm.     

Application of silicon polymer as positive photosensitive material

A new positive-working photosensitive system of silicon polymer, containing silylether groups in the main chain and a photo-induced acid precursor was investigated. The silicon polymer is hydrolized by a photogenerated acid and degraded to low molecular weight compounds. Thus the effect of solubility inhibition of the polymer is diminished. The higher photosensitivity of this system as compared with 1,2-quinone diazide compounds is due to the catalytic reaction of the acid on the hydrolysis of the silicon polymer. The chemical structure around silylether groups in the polymer, in particular more hydrophilic and less steric structures, affects the rate of hydrolysis and thus the photosensitivity. Among various types of photo-induced acid precursors examined, e.g., s-triazine and 1,3,4-oxadiazole compounds substituted by trihalomethyl groups were effective.