New 1-(2-chloroquinolin-3-yl)-4-dimethylamino-2-(naphthalen-1-yl)-1-phenylbutan-2-ols with antituberculosis activity

Russian Chemical Bulletin - New 4-dimethylamino-2-(naphthalen-1-yl)-1-phenyl-1-(quinolin-3-yl)butan-2-ols with antituberculosis activity were synthesized....     

Synthesis,Characterization, and Antioxidant Properties of Novel 1-(4-Aryl-1,3-thiazol-2-yl)-2-{[1-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methylidene}hydrazines

Russian Journal of Organic Chemistry - A series of novel 1-(4-aryl-1,3-thiazol-2-yl)-2-{[1-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyli­dene}hydrazines were synthesized and properly...     

Transamination of cyanothioacetamide with morpholine. Molecular and crystal structure of 3-(morpholin-1-yl)-3-thioxopropanenitrile and 3-(morpholin-1-yl)-3-thioxopropanethioamide

Transamination of cyanothioacetamide with equimolar amount of morpholine resulted in the formation of 3-(morpholin-1-yl)-3-thioxopropanenitrile, and with twofold excess of morpholine 3-(morpholin-1-yl)-3-thioxopropanethioamide was obtained. By the alkylation of the resulting products 2-[2-(morpholin-1-yl)-2-thioxoethylidene]thiazolidin-4-one, 3-amino-N-(4-acetylphenyl)-5-(morpholin-1-yl)-thiophene-2-carboxamide, 3-amino-3-methylthio-1-morpholinoprop-2-ene-1-thione, (2E,4E)-2-(morpholin-4-yl)thiocarbonyl)-5-phenylpenta-2,4-dienothioamide, and 3-{2??-[2??-(molrpholin-1-yl)-2-thioxoethyl]thiazol-4??-yl}-2H-chromen-2-one were synthesized. The 3-(morpholin-1-yl)-3-thioxopropanenitrile and 3-(morpholin-1-yl)-3-thioxopropanethioamide structures were studied by the X-ray diffraction.     

N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)酰胺类新化合物的合成及生物活性

以N-吡啶基吡唑甲酸和2-氨基-3-甲基苯甲酸为起始原料,经由亲核加成、环化和酰化等多步反应合成了一系列结构新颖的N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)酰胺类化合物.测试了所合成化合物的杀虫及抑菌活性,结果表明,新化合物大多化合物在200 mg·L^-1浓度下对东方粘虫(Mythimna separataWalker)具有一定的杀虫活性,尤其是N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)乙酰胺(8a)和N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-3-氯-2,2-二甲基丙酰胺(8e)致死率可达70%;部分化合物在50 mg·L^-1浓度下对油菜菌核病菌的抑菌活性相对较好(54.5%~63.6%),优于triadimefon和chlorantraniliprole;部分化合物如N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-3,3-二甲基丁酰胺80和N-(2-(5-(3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基)-1,3,4-噁二唑-2-基)-4-氯-6-甲基苯基)-4-氟苯甲酰胺(8h)对苹果轮纹病菌具有中等抑菌活性.值得注意的是,化合物8e的杀粘虫活性和对油菜菌核病菌的抑菌活性都较为突出,可用作新农药创制研究的新型参考结构.     

Synthesis and antimycobacterial screening of new 4-(4-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-3-yl)quinoline derivatives

A new series of 4-(4-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-3-yl)quinoline ( 6a-t ) have been synthesized by a click reaction of 4-(4-ethynyl-1-phenyl-1H-pyrazol-3-yl)quinoline ( 4a-d ) with a substituted benzyl azide ( 5a-e ). The starting alkyne derivatives 4a-d are obtained from Bestmann-Ohira reaction of 1-phenyl-3-(quinolin-4-yl)-1H-pyrazole-4-carbaldehyde and dimethyl(1-diazo-2-oxopropyl)phosphonate. The newly synthesized compounds are screened against M. tuberculosis H37Ra dormant and active, Escherichia coli, Pseudomonas fluorescence, Staphylococcus aureus and Bacillus subtilis strains at 30 μg/mL concentration. Most of the screened compounds showed good to moderate antibacterial activity against S. aureus, B. subtilis, and Mycobacterium tuberculosis H37Ra strains. The synthesized derivatives of quinolinyl-pyrazole-4-carbaldehyde and quinolinyl-pyrazole-4-ethyne reportd good to moderate activity against both strains of M. tuberculosis H37Ra. Ten derivatives of quinolinyl-pyrazole presented good activity against B. subtilis. These results suggested that further optimization and development of quinolinyl-pyrazolyl-1,2,3-triazole moeity could serve as lead compounds for antimycobacterial activity.     

Solvent-free reaction of 3-aryl-6-(3-nitrophenyl)-1,2,4-triazines with 4-(cyclohex-1-en-1-yl)morpholine

The aza-Diels–Alder reaction of 3-aryl-6-(3-nitrophenyl)-1,2,4-triazines with 4-(cyclohex-1-en-1-yl)morpholine as dienophile was accompanied by reduction of the nitro group to amino. In the reaction of 3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1,2,4-triazine with 4-(cyclohex-1-en-1-yl)morpholine, 3-[3-(4-methoxyphenyl)-1,2,4-triazin-6-yl)aniline was formed together with the cycloaddition product.     

Synthesis of 1-(4-butoxyphenyl)-1-cyclohexyl-3-(4-arylpiperazin-1-yl)-2-phenylpropan-1-ols and their dihydrochlorides

Aminomethylation of 1-(4-butoxyphenyl)-2-phenylethanone with paraformaldehyde and substituted piperazines in ethanol medium results in 1-(4-butoxyphenyl)-3-(4-R-piperazin-1-yl)-2-phenylpropan-1-ones. The latter react with cyclohexylmagnesium halide to give 1-(4-butoxyphenyl)-1-cyclohexyl-3-(4-arylpiperazin-1-yl)-2-phenylpropan-1-ols. Reduction of the prepared β-aminoketones with lithium aluminum hydride in absolute diethyl ether leads to the secondary aminopropanols. The prepared compounds could be converted into the corresponding dihydrochlorides.     

Synthesis of 3-(2-Phenylquinolin-4-yl)/3-(l-p-Chlorophenyl-5-methyl-1, 2,3-triazol-4-yl)-s-triazolo[3,4-b]-1, 3,4-thiadiazine Derivatives

s-Triazolo[3, 4-b]-1,3,4-thiadiazine derivatives constitute an important class of organic compounds with diverse biological activities. 2-Phenylquinoline and 1,2, 3-triazole derivatives are very attractive heterocyclic systems due to their wide use in medicine, agriculture and industry^[1]. Incorporation of 2-phenylquinoline and 1,2,3-triazole moiety into the 3-position of s-triazolo[3,4-b]-l, 3,4-thiadiazine ring system may enhance their biological activity. In light of the above findings, we synthesized some new s-triazolo[3, 4-b]-1, 3, 4-thiadiazine derivatives 2a-b~6a-b by the condensation of 4-amino-5-mercapto-3-(2-phenylquinolin-4-yl)/3-(1-p-chlorophenyl-5-methyl-1, 2,3-triazol-4-yl)-1, 2, 4-triazoles 1a-b with chloroacetalde-hyde, ω-bromo-ω-(1H-1, 2, 4-triazol-1-yl)acetophenone, chloranil, 2-bromocyclohexanone, 2, 4'-dibromoacetophenone, respectively.     

Microwave Assisted Synthesis and Antimicrobial Activity of (E)-1-{2/3/4-[(1-Aryl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-3-(2-morpholinoquinolin-3-yl)prop-2-en-1-ones

Russian Journal of General Chemistry - A novel series of (E)-1-{2/3/4-[(1-aryl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-3-(2-morpholinoquinolin-3-yl)prop-2-en-1-ones is synthesised from terminal...     

N-甲基-2-(4-取代哌嗪)-N-[3-(萘氧基)-3-(2-噻吩基)丙基]乙酰胺衍生物的设计与合成

以N-甲基-3-(1-萘氧基)-3-(2-噻吩基)-丙胺(度洛西汀)为原料,通过N-酰氯化反应和N-烷基化反应,合成了5个新型的N-甲基-2-(4-取代哌嗪)-N-[3-(萘氧基)-3-(2-噻吩基)丙基]酰胺衍生物,其结构经1H NMR,IR和MS表征。     

Synthesis of C-Nucleoside Analogues： 2-[2-（Hydroxymethyl）-1, 3-dioxolan-5-yl]1, 3-thiazole-4-carboxamide and 2-[2-（Mercaptometh-yl）-1, 3-dioxolan-5-yl] 1, 3-thiazole-4-carboxamide

Novel C-nucleosides of tiazofurin analogue (2-[2-(hydroxymethyl)-1,3-dioxolan-5-yl] 1,3-thiazole-4-carboxamide) and its thiol-substituted derivative (2-[2-(mercaptomethyl)-1,3-dioxolan-5-yl] 1, 3-thiazole-4-carboxamide) were synthesized from methyl acrylate through a multistep procedure. Their structures were confirmed by IR, ^1HNMR, ^13CNMR and elemental analysis.     

Synthesis of 3-[5-(biphenyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones by palladium-free cross-coupling between pyrroles and haloalkynes on aluminum oxide

Cross-coupling of 2-(biphenyl-4-yl)pyrroles derived from 1-(biphenyl-4-yl)ethanone oximes and acetylene with 3-bromo-1-phenylprop-2-yn-1-one on aluminum oxide gave 3-[5-(biphe-nyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones in 35–46% yields.     

Theoretical study on the geometry and vibration of 1-[6-(4-Chlorophenyl)-1-[(6-chloropyridin-3-yl)methyl]-2-[(6-chloropyridin-3-yl)methylsulfanyl]-4-methyl-1,6-dihydropyrimidin-5-yl]ethanone

The solid phase FT-IR and FT-Raman spectra of 1-[6-(4-chlorophenyl)-1-[(6-chloropyridin-3-yl)methyl]-2-[(6-chloropyridin-3-yl)methylsulfanyl]-4-methyl-1,6-dihydropyrimidin-5-yl]ethanone (C25H21Cl3N4OS) were recorded in the region 4000-400 and 3500-100cm(-1), respectively. The vibrational spectra have been computed using density functional theory (B3LYP) and ab initio molecular orbital calculation (HF) with 6-31G(d, p) basis sets. A close agreement was achieved between the observed and calculated frequency by employing normal coordinate calculations. The observed and simulated spectra were found to be well comparable.     

Ensembles of rings with a coumarin unit 1. Synthesis of 3-(2-R-thiazol-4-yl)-and 3-(4-R-thiazol-2-yl)coumarins

We have synthesized 3-(2-R-thiazol-4-yl)coumarins (R=H, CH₃, CH₂CN, Ar) by condensation of 3-(-bromoacetyl)coumarins with thioamides. We obtained 3-(4-R-thiazol-2-yl)coumarins (R=H, Ar) by several methods. By reaction of 2-cyanomethyl-4-phenylthiazole with 2-hydroxybenzaldehydes, we synthesized 2-imino-3-(4-phenylthiazol-2-yl)coumarins, which were converted to the corresponding coumarins by acid hydrolysis. For 3-(2-R-thiazol-4-yl)coumarins (R=CH₂CN), we carried out reactions with aromatic aldehydes. We propose alternative methods for synthesis of 2-[2-aryl(hetaryl)-1-cyanoethenyl]-4-(coumarin-3-yl)thiazoles.Ukrainian Pharmaceutical Academy, Kharkov 310002. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1345–1355, October, 1997.     

Solvent-free microwave assisted synthesis of substituted (E)-phenyl{3-(2-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]vinyl)benzofuran-2-yl}methanones and their antimicrobial activity

Russian Journal of General Chemistry - New substituted (E)-phenyl{3-(2-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]vinyl)benzofuran-2-yl}methanones have been synthesized from substituted...     

Synthetic cephalosporins. VI. Synthesis and antibacterial activity of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxy-1-methyl) ethoxyiminoacetamido]- 3-(3-hydroxy-4-pyridon-1-yl)methyl-3-cephem-4-carboxylic acid and related compounds

Synthesis and antibacterial activity of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxy-1-methyl)ethoxyimin oacetamido]- 3-(3-hydroxy-4-pyridon-1-yl)-3-cephem-4-carboxylic acid (12) and its related compounds are described. Compound 12 exhibited excellent antibacterial activity against gram-negative bacteria, and its anti-pseudomonal activity was ten to fifteen times greater than that of ceftazidime.     

Synthesis of Geminally Activated 4-(Furan-2-yl)- and 4-(Thiophen-2-yl)-1-nitrobuta-1,3-dienes

The condensation of 3-(furan-2-yl)- and 3-(thiophen-2-yl)prop-2-enals with nitro-substituted CH acids, namely ethyl nitroacetate, nitroacetone, nitroacetophenone, and nitroacetonitrile, afforded a series of geminally activated nitro dienes, 4-(furan-2-yl)- and 4-(thiophen-2-yl)-1-nitrobuta-1,3-dienes. The product structure was confirmed by NMR and IR spectroscopy.

     

4-(3-Dialkylamino-2,5-dioxopyrrolidin-1-yl)benzoic acid esters

Reactions of alkyl 4-aminobenzoates with maleic anhydride give the corresponding alkyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoates, and the latter are converted into 4-(3-dialkylamino-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrol-1-yl)benzoates by treatment with secondary amines.     

Synthetic cephalosporins. VII. Synthesis and antibacterial activity of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(3-(3-hydroxy-4-pyridon-1-yl)-3- carboxypropoxyimino)acetamido]-3-(1,2,3-thiadiazol-5-yl)-thiomethyl-3- cephem-4-carboxylic acid and its related compounds

Synthesis and antibacterial activity of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(3-(3-hydroxy-4-pyridon-1-y l)-3- carboxypropoxyimino)acetamido]-3-(1,2,3-thiadiazol-5-yl)thio methyl-3-cephem-4-carboxylic acid (12a) and its related compounds are described. Compound 12a exhibited excellent antibacterial activity against gram-negative bacteria, including Pseudomonas aeruginosa.     

Synthesis of Fluorine-Containing 2-(1-Aryl-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic Acids

Acid hydrolysis of ethyl 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetates gives 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2,2-dihydroxyacetic acids which undergo dehydration on heating in toluene to afford 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic acids. Reactions of the latter with excess morpholine result in replacement of two fluorine atoms in positions 5 and 7 by the amine residues.