Synthesis and properties of a novel fluorescent nucleobase, naphthopyridopyrimidine

A new base-discriminating fluorescent nucleoside, NPP, that can sharply distinguish between A and G bases opposite NPP is described. The hybridization of an ODN probe containing NPP with a target DNA facilitates the judgment of the type of purine base located at a specific site on the target DNA.     

Synthesis and triplex-forming ability of 2',4'-BNAs bearing imidazoles as a nucleobase

To expand the sequence of double-stranded DNA (dsDNA) targets in a triplex formation, 2',4'-BNAs (2'-O,4'-C-methylene bridged nucleic acids) having imidazoles as a nucleobase were synthesized and incorporated into oligonucleotides. Triplex-forming ability of the modified oligonucleotides was evaluated by using melting temperature (Tm) measurements.     

2-苯硫基苯并咪唑的合成

在不使用金属催化剂、配体及强碱的情况下,以DMF为溶剂,于130℃反应24 h,2-巯基苯并咪唑与二苯基碘三氟甲磺酸盐高选择性地发生芳基化反应,合成了2-苯硫基苯并咪唑,收率80.7%,其结构经1H NMR和13C NMR确证。     

Bis-arylsulfonamide Derivatives of 2-Amino-5(6)-(4-aminophenylthio)benzimidazole

Three different procedures have been developed for the preparation of bis-arylsulfonamide derivatives of 2-amino-5(6)-(4-aminophenylthio)benzimidazole, and biological activity of the products have been studied.     

Synthesis and properties of 1,3-diphenyl-5-(benzothiazol-2-yl)-6-R-verdazyls

1. Download high-res image (102KB)
2. Download full-size image

     

微波辐射快速合成2-(2＇-羟苯基)-5(6)取代苯并咪唑衍生物

苯并咪唑衍生物具有一定的抗病毒能力[1],一些苯并咪唑衍生物已用作农用抗植物病毒剂[2].一锅煮合成反应时间较长,产率中等[3,4].本文用取代邻苯二胺和水杨酸为原料,吡啶为溶剂,POCl3为催化剂,微波辐射法合成了标题化合物.     

Structures and luminescence properties of two copper(I) halide complexes featuring 2-(2-benzimidazolyl)-6-methylpyridine

Two new copper（I） halide complexes bearing 2-（2-benzimidazolyl）-6-methylpyridine（Hbmp） and PPh₃ ligands, Cu（Hbmp）（PPh₃）X（X = Br（1）;I（2））,have been synthesized and characterized.Single-crystal X-ray structure analysis reveals that the halide ligand has a significant impact on the Cu-N_pyridyl bond lengths.Complexes 1 and 2 show the solid-state emissions at ambient temperature,varying with the halide bound to the {Cu（Hbmp）（PPh₃）} motif,which are perhaps best attributed to the metal-to-ligand charge-transfer（Cu（I）→Hbmp） transition mixed with some ligand-to-ligand charge-transfer（X and PPh₃→Hbmp） character.     

Synthesis and spectral-luminescence properties of 2-(2′-tosylaminophenyl)benzimidazole and its substituted derivatives

Tosylamino-substituted 2-arylbenzimidazoles have blue or green fluorescence in the crystalline state and in toluene at room temperature. The effect of the substituents on the position of the absorption and fluorescence bands and on the strength of the intramolecular hydrogen bond was investigated. An anomalously large Stokesian shift within the limits 8800–11450 cm^¡1 is characteristic for compounds that contain an o-tosylamino group.     

Stereoselective Synthesis of (6R)-6-(5-Methyl-2-furyl)-2-oxocyclohexanecarboxyl-10', 2'-Sultam

PseudolaricacidA(l)whichexhibitsantifungalandantifertilityactivitieswasisolatedfromPeudolarl-xKaenlpjbriGord'.Theabsoluteconfigurationsofthesechiralcenterswereassignedtobe3S,4S,10RandIIRrespectively'.Accordingtotheretrosyfltheticanalysis.theskeletonofIcouldbeconstructedbyintramolecular[4- 31cycloadditiontyomaseven-memberedlactone2(Schemel)whichcouldbeobtainedfrom(6S)-6-Thesynthesisbeganwithbetalprotected0-ketoacid4,tbllowedbyamidationwith(-)-camphorsultamandDCCtoobtainapairofdiastereomer…     

Promotion of stable triplex formation by partial incorporation of 2',5'-phosphodiester linkages into triplex-forming oligonucleotides

Pentadecamer homopyrimidine oligonucleotides containing three or more 2',5'-phosphodiester linkages in different modes were prepared and used to evaluate the ability as a triplex-forming oligonucleotide (TFO), and it was found that discontinuous replacement of the 3',5'-phosphodiester linkages in TFO by 2',5'-linkages significantly stabilizes parallel-motif triplexes.     

Synthesis of Methyl 5(6)-(4-Aminophenoxy)- and 5(6)-(2-Aminophenoxy)-2-benzimidazolyl Carbamates and Their Biological Properties

A procedure was developed for preparation of methyl 5(6)-(4-aminophenoxy)- and 5(6)-(2-aminophenoxy)-2-benzimidazolyl carbamates by reaction of 3,4,4`-triaminodiphenyl or 3,4,2`-triaminodiphenyl ethers respectively with methyl cyanocarbamate in water solution in the presence of 7-10 molar excess of acetic acid. The helminthicidal properties, embryotoxicity, and overall toxicity of compounds obtained were estimated.     

2-(5-Hydrazinocarbonyl-2-thienyl) -5, 6-methylenedioxybenzofuran and 2-(5-hydrazinocarbonyl-2-furyl)-5, 6-methylenedioxybenzofuran as novel fluorescence derivatisation reagents for carboxylic acids in liquid chromatography

The new acid hydrazides, 2-(5-hydrazinocarbonyl-2-thienyl)-5,6-methylenedioxybenzofuran (TMBH) and 2-(5-hydrazin-ocarbonyl-2-furyl)-5, 6-methylenedioxybenzofuran (FMBH), were synthesized as precolumn fluorescence derivatisation reagents for carboxylic acids in liquid chromatography. These compounds readily react with carboxylic acids in the presence of a coupling reagent under mild conditions in aqueous solution to give fluorescent derivatives. The detection limits of lauric acid were both 0.1 pmol per 10 μl injection volume at a signal-to-noise ratio of 3. The methods in which these compounds are used were applied to the assay of a standard mixture of prostaglandins (25 μM) and prostaglandins in a human seminal fluid.     

Synthesis and thermotropic studies of a novel series of nematogenic liquid crystals 2-(6-alkoxynaphthalen-2-yl)-5-cyanopyridines

A novel series of highly birefringent liquid crystalline compounds, 2-(6-alkoxynaphthalen-2-yl)-5-cyanopyridines (nO-NpPyCN, n?=?2–8) that have potential as commercially useful, were synthesised using a short two-step reaction with overall yields between 55% and 85%. Spectral analyses were in accordance with the expected structures. Their thermotropic behaviours were investigated by polarising optical microscopy and differential scanning calorimetry. It was found that the desymmetrised core results in a nematic phase with a broad mesophase range.     

Synthesis and properties of 5-(5-nitro-2-furyl)thiazolines

The reactions of 2-amino-4-methyl-5-(5-nitro-2-furyl)thiazole with excess methyl iodide leads to 3,4-dimethyl-2-methylamino-5-(5-nitro-2-furyl)thiazolium iodide, which is converted to 2-imino-3,4-dimethyl-5-(5-nitro-2-furyl)thiazoline under the influence of bases. The iminothiazoline structure was proved by comparison of the spectral characteristics of its acetyl derivative and the isomeric 2-(N-acetyl-N-methyl) amino-4-methyl-5-(5-nitro-2-furyl)thiazole. The pKa values of 2-amino-4-methyl-5-(5-nitro-2-furyl)thiazole and 3,4-dimethyl-2-imino-5-(5-nitro-2-furyl)-thiazoline were determined, and the constant of the aminothiazole-iminothiazoline tautomeric equilibrium was calculated.Translated from Khimiya Geterosiklicheskikh Soedinenii, No. 10, pp. 1337–1340, October, 1985.     

Synthesis and properties of 1-(6-methoxy)-2-benzothiazolyl)-2-pyridones

Substituted ]-(6-methoxy-2-benzothiazolyt)-2-pyridones were prepared from 2-amino-6-methoxybenzathiazate through N-(6-methoxy-2-benzothiazotyl) cyanvorearmileaznd-3-aryl-N-(6-methoxy-2-benzothiazolyt)-2-cyano-2-propenamides. The cyclization of the latter with malonodinitrile in the presence of piperidine gave the corresponding pyridones. The structures of the synthesized compounds were confirmed by¹H NMR and mass spectral data.Department of Organic Chemistry, Mass Spectrometry Laboratory, Slovak Technical University, 812 37 Bratislava, Slovakia. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1402–1404, October, 1995. Original article submitted August 24, 1995.     

Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole

The synthesis of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole, which undergoes a nucleophilic substitution with pyridine in the absence of additional base, is reported. The key steps are the reaction of 1,2-phenylenediamine to give exclusively the mono-substituted product and the avoidance of minor by-products via the use of glycolic acid for the cyclisation step. The X-ray structures of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazolium chloride and 1-[1-(4-nitrobenzyl)benzimidazol-2-ylmethyl]pyridinium chloride are presented.     

Chemistry of 2-hetarylbenzimidazoles. 8. Synthesis and properties of 1-methyl-2-(5′-methyl-2′-selenienyl)benzimidazole

1-Methyl-2-(5-methyl-2-selenienyl)benzimidazole was synthesized and subjected to electrophilic-substitution reactions: nitration, bromination, sulfonation, chloromethylation, formylation, and acylation. The substituent usually enters the 4 position of the selenophene ring, but nitration with acetyl nitrate leads to a mixture of 5-nitro and 4-nitro derivatives. Oxidation of 2-selenienylbenzimidazole with potassium permanganate leads to the 5-carboxy derivative, while oxidation with selenium dioxide leads to the 5-hydroxymethyl and 5-formyl derivatives.See [1] for Communication 7.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1636–1639, December, 1987.     

2-乙氧羰基-6-(2-苯并咪唑基)吡啶锌配合物的合成、表征及荧光性质

以2-乙氧羰基-6-(2-苯并咪唑基)吡啶为配体,通过液相反应合成了其与氯化锌的金属配合物,通过元素分析、摩尔电导率、红外光谱、紫外光谱、热重等对配合物进行了表征,并利用荧光光谱研究了它的发光性质。结果表明,在360nm紫外光激发下,固体配合物能发射出较强的蓝色荧光,最大发射波长为440nm,具有很好的荧光性质和较高的热稳定性,可以作为一种潜在的荧光光学材料。