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1.
Seo Y Park KE Kim YA Lee HJ Yoo JS Ahn JW Lee BJ 《Chemical & pharmaceutical bulletin》2006,54(12):1730-1733
Thunbergols A (4) and B (5), tetraprenyltoluquinols, along with three known compounds (1-3) have been isolated from the brown alga Sargassum thunbergii. The structures of these two new compounds were determined to be 9-(3,4-dihydro-2,8-dimethyl-6-hydroxy-2H-1-benzopyran-2-yl)-6-methyl-2-(4-methyl-3-pentenyl)-(2E,6E)-nonadienoic acid (4) and 10-(2,3-dihydro-5-hydroxy-7-methyl-1-benzofuran-2-yl)-10-hydroxy-6-methyl-2-(4-methyl-3-pentenyl)-(2E,6E)-undecadienoic acid (5), respectively, by combined spectroscopic methods. Both of them exhibited significant scavenging activities on radical and potently inhibited generation of ONOO(-) from morpholinosydnonimine (SIN-1). 相似文献
2.
Isoprenylated flavonoids 5,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-3,6,4'-trimethoxyflavone (1), 3,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-5,6,4'-trimethoxyflavone (2) and an isoprenylated acetophenone derivative (3) have been isolated from Duranta repens along with known compounds, 5-hydroxy-3,6,7,4'-tetramethoxyflavone (4), rosenonolactone (5), 6,7-dimethoxycoumarin (6), 5alpha,8alpha-epidioxyergosta-6,22-dien-3beta-ol (7) and 5alpha,8alpha-epidioxyergosta-6,9(11),22-trien-3beta-ol (8), isolated for the first time from this species. Their structures and the relative configuration were determined by spectroscopic methods (1H- and 13C-NMR, IR, UV and MS) and two-dimensional (2D)-NMR experiments. The compounds 1-5 showed inhibitory activity against prolyl endopeptidase while 4 and 5 were also active against thrombin. 相似文献
3.
Lácová M Puchala A Solcanyova E Lac J Kois P Chovancova J Rasala D 《Molecules (Basel, Switzerland)》2005,10(7):809-821
One-pot and facile preparations of 6-(2-hydroxy-5-R-benzoyl)-4-methyl-2-R1- pyrazolo[3,4-b]pyridines 4a-o are described, using the reaction of 3-formyl chromones 1 with 5-amino-1-R1-pyrazoles 2. An enamine-intermediate 2-ethyloxy-6-R-3-(3-methyl-1- phenylpyrazol-5-ylaminomethylene)chroman-4-one 3 was isolated at lower temperatures. Acyloxy-derivatives 5 of compounds 4 were obtained by acylation with acid chlorides or acid anhydrides. Coumarins 6 substituted at the 3- and 4-positions were prepared from the pyrazolo[3,4-b]pyridines 4 by condensation reactions and hydrazones 7 were formed from their reaction with 2,4-dinitrophenyl hydrazine. Reactions under microwave irradiation proceeded significantly faster and with high yields. 相似文献
4.
Tetsuji Kametani Kazuo Kigasawa Mineharu Hiiragi Nagatoshi Wagatsuma Tuneo Uryu Hideo Sugi 《Journal of heterocyclic chemistry》1973,10(1):27-29
Treatment of 1,2,5,6-tetrahydro-2-(4-hydroxy- and/or 4-methoxybenzyl)-3,4-dimethyl-I-(3-methyl-2-butenyl)pyridines (IV and V) and 2-(4-methoxybenzyl)-3,4-dimethyl-1-(3-methyl-2-butenyl)-4-piperidinol (X) with acid afforded 9-(4-hydroxy- and/or 4-methoxybenzyl)-4,4,5,6-tetramethyl-1-azabicyelo[3,3,1]non-6-ene (XIII and XIV). In contrast, the corresponding 1-allyl-substituted derivatives VI, VII, and XI were converted into the expected 3-allyl-1,2,3,4,5,6-hexahydro-8-hydroxy- and/or 8-methoxy-6,11-dimethyl-2,6-methano-3-benzazocine (II and III). 相似文献
5.
Isothiazolopyridines, pyridothiazines and pyridothiazepines are important compounds that possess valuable biological activities. This paper reports on the synthesis of these compounds using both conventional chemical methods and modern microwave techniques. 3-Bromo-6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide, 5-arylazo-6-hydroxy-4-methyl-2-thioxo-1,2-dihydropyridine-3-carboxamides, 3,5-bis-arylazo-6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-caboxamide, 4-methyl-2,3,6,7-tetra-hydroisothiazolo[5,4-b]-pyridine-3,6-dione, 2,2'-(methylene-bis-(sulfanediyl))bis(4-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide), 2-hydroxy-5-methyl-4H-pyrido[3,2-e][1,3]-thiazine-4,7(8H)-dione and 2-arylmethylene-8-hydroxy-6-methyl-2,3,4,5-tetrahydropyrido-[3,2-f][1,4]thiazepine-3,5-diones have been prepared from 6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide. Some of these compounds were prepared using microwave-assisted reaction conditions, that provided higher yields in shorter times than the conventional methods. 相似文献
6.
A mixture of 3-(α,β-epoxyisopropyl)-1-phenyl-2-azetidinone and benzylamine was heated in a sealed tube at 120–130° yielding 4-anilinomethyl-1-benzyl-3-hydroxy-3-methyl-2-pyrrolidinone as a mixture of diastereoisomers. By this method, 4-anilinomethyl-3-hydroxy-3-methyl-1-phenyl-2-pyrrolidinone and 4-anilinomethyl-3-hydroxy-3-methyl-1-(3,4-dimethoxyphenethyl)-2-pyrrolidinone were obtained by using aniline and 3,4-dimethoxyphenethylamine, respectively, instead of benzylamine. The reaction of 4-formyl-1-phenyl-2-azetidinone with 3,4-dimethoxyphenethylamine afforded 4-anilino-1-(3,4-dimethoxyphenethyl)-2,3-dihydro-2-oxopyrrole. In a similar fashion, the 1-n-butyl and 1-isobutyl analogues were obtained by the use of n-butylamine and isobutylamine, respectively, instead of 3,4-dimethoxyphenethylamine. 相似文献
7.
The reaction between 2-hydroxybenzaldehyde and 4-hydroxy-6-methyl-2-pyrone (triacetic acid lactone) affords 3-acetoacetyl-2-chromenone, 7 , instead of 3-(2-hydroxybenzylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione, 6 . The structures previously reported in the literature for the products formed in the reactions of 4-hydroxy-2-chromenone with 2-hydroxybenzaldehydes in a molar ratio 1:1 are considered erroneous. Thus, the previously reported 3-(2-hydroxybenzylidene)chroman-2,4-dione, 10 , should be formulated as 3-(2-hydroxybenzoyl)-2-chromenone, 11 . 相似文献
8.
Bade Thirupaiah 《合成通讯》2014,44(4):513-519
A one-pot procedure has been developed for the synthesis of substituted 2,3-dihydro-2-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazin-3-yl)phthalazine-1,4-diones by reaction of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and phthalic anhydrides in acetic acid medium. Similarly, a one-pot, three-component synthetic procedure has been developed for substituted 3-[3-(N1-benzylidene-hydrazino)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-4-hydroxy-6-methyl-pyran-2-ones from 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and various aromatic aldehydes in absolute ethanol and a few drops of glacial acetic acid.
[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] 相似文献
9.
Yoshihisa Kurasawa Tomomi Kureyama Noriko Yoshishiba Ritsuko Katoh Atsushi Takada Ho Sik Kim Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1993,30(2):537-541
The reaction of 6-chloro-2-(1-methylhydrazino)quinoxaline 4-oxide 8 with furfural, 3-methyl-2-thiophene-carbaldehyde, 2-pyrrolecarbaldehyde, 4-pyridinecarbaldehyde and pyridoxal hydrochloride gave 6-chloro-2-[2-(2-furylmethylene)-1-methylhydrazino]quinoxaline 4-oxide 5a , 6-chloro-2-[1-methyl-2-(3-methyl-2-thienyl-methylene)hydrazino]quinoxaline 4-oxide 5b , 6-chloro-2-[1-methyl-2-(2-pyrrolylmethylene)hydrazino]quinoxa-line 4-oxide 5c , 6-chloro-2-[1-methyl-2-(4-pyridylmethylene)hydrazino]quinoxaline 4-oxide 5d and 6-chloro-2-[2-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridylmethylene)-1-methylhydrazino]quinoxalme 4-oxide 5e , respectively. The reaction of compound 5a or 5b with 2-chloroacrylonitrile afforded 8-chloro-3-(2-furyl)-4-hydroxy-1-methyl-2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline-5-carbonitrile 6a or 8-chloro-4-hydroxy-1-methyl-3-(3-methyl-2-thienyl)-2,3-dihydro-1H-1,2-diazepino[3,4-b]quinoxaline-5-carbonitrile 6b , respectively, while the reaction of compound 5e with 2-chloroacrylonitrile furnished 11-chloro-7,13-dihydro-4-hydroxy-methyl-5,14-methano-1,7-dimethyl-16-oxopyrido[3′,4′:9,8][1,5,6]oxadiazonino[3,4-b]quinoxaline 7. 相似文献
10.
Anis E Anis I Ahmed S Mustafa G Malik A Afza N Hai SM Shahzad-ul-hussan S Choudhary MI 《Chemical & pharmaceutical bulletin》2002,50(1):112-114
Two new compounds, 7'-(3',4'-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (4), and 7'-(4'-hydroxy,3'-methoxyphenyl)-N-[(4-butylphenyl)ethyl]propenamide (5) have been isolated from Cuscuta reflexa along with five known compounds, 6,7-dimethoxy-2H-1-benzopyran-2-one (1), 3-(3,4-dihydroxyphenyl)-2-propen-1-ethanoate (2), 6,7,8-trimethoxy-2H-1-benzopyran-2-one (3), 3-(4-O-beta-D-glucopyranoside-3,5-dimethoxyphenyl)-2-propen-1-ol (6), 2-(3-hydroxy-4-methoxyphenyl)-3,5-dihydroxy-7-O-beta-D-glucopyranoside-4H-1-benzopyrane-4-one (7), reported for the first time from this species. Structures of these compounds were determined by spectral analysis. These compounds showed strong inhibitory activity against alpha-glucosidase. 相似文献
11.
P. P. Mukovoz A. V. Gorbunova V. O. Koz’minykh P. A. Slepukhin I. N. Ganebnykh O. S. El’tsov E. N. Koz’minykh 《Russian Journal of Organic Chemistry》2016,52(7):993-999
Methyl 3,4-dihydroxy-6-oxoalka-2,4-dienoates reacted with anthranilic acid hydrazide to give methyl [5-alkyl-1-(2-aminobenzamido)-2-hydroxy-3-oxo-2,3-dihydro-1H-pyrrol-2-yl]acetates. The reaction of anthranilic acid hydrazide with ethyl 3,4-dihydroxy-6-oxohepta-2,4-dienoate afforded ethyl (2Z)-(3a-hydroxy-2-methyl-10-oxo-3,3a,5,10-tetrahydro-4H-pyrazolo[5,1-c][1,4]benzodiazepin-4-ylidene)acetate as solvate with one methanol molecule. The structure of the isolated compounds was determined on the basis of IR and NMR spectra and X-ray diffraction data. 相似文献
12.
Thymidine and uridine were modified at the C2' and C5' ribose positions to form amine analogues of the nucleosides (1 and 4). Direct amination with NaBH(OAc)3 in DCE with the appropriate aldehydes yielded 1-{5-[(bis(pyridin-2-ylmethyl)amino)methyl]-4-hydroxytetrahydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (L1), 1-{5-[(bis(quinolin-2-ylmethyl)amino)methyl]-4-hydroxytetrahydrofuran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione (L2), and 1-[3-(bis(pyridin-2-ylmethyl)amino)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione (L5), while standard coupling procedures of 1 and 4 with 5-(bis(pyridin-2-ylmethyl)amino)pentanoic acid (2) and 5-(bis(quinolin-2-ylmethyl)amino)pentanoic acid (3) in the presence of HOBT-EDCI in DMF provided a second novel series of bifunctional chelators: 5-(bis(pyridin-2-ylmethyl)amino)pentanoic acid [(3-hydroxy-5-(5-methyl-4-oxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-yl)methyl] amide (L3), 5-(bis(quinolin-2-ylmethyl)amino)pentanoic acid [(3-hydroxy-5-(5-methyl-4-oxo-3,4-dihydro-2H-pyrimidin-1-yl)tetrahydrofuran-2-yl)methyl] amide (L4), 5-(bis(pyridin-2-ylmethyl)amino)pentanoic acid [2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] amide (L6), and 5-(bis(quinolin-2-ylmethyl)amino)pentanoic acid [2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl] amide (L7). The rhenium tricarbonyl complexes of L1-L4, L6, and L7, [Re(CO)3(LX)]Br (X=1-4, 6, 7: compounds 5-10, respectively), have been prepared by reacting the appropriate ligand with [NEt4][Re(CO)3Br3] in methanol. The ligands and their rhenium complexes were obtained in good yields and characterized by common spectroscopic techniques including 1D and 2D NMR, HRMS, IR, cyclic voltammetry, UV, and luminescence spectroscopy and X-ray crystallography. The crystal structure of complex 6.0.5NaPF6 displays a facial geometry of the carbonyl ligands. The nitrogen donors of the tridentate ligand complete the distorted octahedral spheres of the complex. Crystal data: monoclinic, C2, a = 24.618(3) A, b = 11.4787(11) A, c = 15.5902(15) A, beta = 112.422(4) degrees , Z = 4, D(calc) = 1.562 g/cm3. 相似文献
13.
7-Acetyl-8-aryl-2-(1-chloro-2-hydroxy-3-propyl)thio-9-cyano-6-methyl-1,4-dihydropyridines were obtained by treatment of 1,4-dihydropyridine-2(3H)-thiones
with epichlorohydrin in the presence of sodium bicarbonate. When treated with NaOMe, these compounds are readily intramolecularly
alkylated with formation of 7-acetyl-8-aryl-3-hydroxy-9-cyano-6-methyl-3,4-dihydro-2H,8H-pyrido[2,1-b]-[1,3]thiazines. We
have studied amination of 2-(1-chloro-2-hydroxy-3-propyl)thio-1,4-dihydropyridines and acylation of 3-hydroxy-3,4-dihydro-2H,8H-pyrido[2,1-b][1,3]thiazines.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1394–1399, September, 2005. 相似文献
14.
7'-(4'-hydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (1), 7'-(3',4'-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (2), N-p-trans-coumaroyltyramine (3), N-trans-caffeoyltyramine (4), beta-sitostenone (5), ferulic acid (6), hydroferulic acid (7), 5-hydroxy-3,4-dimethoxycinnamic acid (8), veratic acid (9), vanillic acid (10), isovanillic acid (11), syringic acid (12), (+)-syringaresinol (13), and pheophorbide a (14) were isolated from the stems of Capsicum annuum (Solanaceae). Among them, 1 is a new amide compound. The structures of these compounds were characterized and identified by spectral analyses. 相似文献
15.
David Miller 《Journal of heterocyclic chemistry》1984,21(4):1025-1027
The rapid addition of methyl lithium to the 4-vinylpyridine system present in 4-{2,6-dihydroxy-4-(3-methyl-2-octyl)phenyl}-2-methyl-4-(4-pyridyl)but-3-en-2-ol ( 2 ) is reported. The α and β-4-{2,6-dihydroxy-4-(3-methyl-2-octyl)phenyl}-2,3-dimethyl-4-(4-pyridyl)butan-2-ols 4 and 5 formed, are cyclised by heating with 5N hydrochloric acid to trans and cis-3,4-dihydro-5-hydroxy-7-(3-methyl-2-octyl)-4-(4-pyridyl)-2,2,3-trimethyl-2H-1-benzopyran 6 and 7 respectively. 相似文献
16.
Zusammenfassung 5-Chlor-2-(N-methyl-jodmethansulfonamido)-benzophenon (6 b) reagiert mit flüss. NH3 zu 6-Chlor-4-hydroxy-1-methyl-4-phenyl-3,4-dihydro-1H-2,1-benzothiazin-2,2-dioxid (7), mit NH3 in absol. Alkohol zu 6-Chlor-4-hydroxy-3-jod-1-methyl-4-phenyl-3,4-dihydro-1H-2,1-benzothiazin-2,2-dioxid (9). Der Mechanismus dieser Reaktionen wird diskutiert.
The reaction of ammonia with 5-Chloro-2-(N-methyl-iodo-methanesulfonamido)-benzophenone
The reaction of 5-chloro-2-(N-methyl-jodomethanesulfon-amido)-benzophenone (6b) with liquid or absol. alcoholic ammonia leads to 6-chloro-4-hydroxy-1-methyl-4-phenyl-3,4-dihydro-1H-2,1-benzothiazine-2,2-dioxid (7) and 6-chloro-4-hydroxy-3-jodo-1-methyl-4-phenyl-3,4-dihydro-1H-2,1-benzothiazine-2,2-dioxid (9) resp. The mechanism of these reactions is discussed.相似文献
17.
A high-performance liquid chromatographic method is described for the determination in human urine and plasma of catecholamines, their precursor and metabolites [amino compounds (norepinephrine, epinephrine, dopamine, normetanephrine, metanephrine, 3-methoxytyramine and L-DOPA), acidic compounds (3,4-dihydroxymandelic acid, 3,4-dihydroxyphenylacetic acid, vanillylmandelic acid and homovanillic acid) and alcoholic compounds (3,4-dihydroxyphenylethyleneglycol and 4-hydroxy-3-methoxyphenylethyleneglycol)]. Urine (0.5 ml) containing 3,4-dihydroxybenzylamine and 4-hydroxy-3-methoxycinnamic acid (internal standards) is deproteinized with perchloric acid, and the resulting solution is fractionated by solid-phase extraction on a strong cation-exchange resin cartridge (Toyopak IC-SP S) into two fractions (amine fraction and acid-alcohol fraction), which include 3,4-dihydroxybenzylamine and 4-hydroxy-3-methoxycinnamic acid, respectively. Plasma (0.7 ml) is deproteinized in the presence of 3,4-dihydroxybenzylamine (internal standard) in the same manner, and the resulting solution is directly used as an acid-alcohol fraction, while an amine fraction is obtained as for urine. Each fraction is subjected to the previously established ion-pair reversed-phase chromatography with post-column derivatization involving coulometric oxidation followed by fluorescence reaction with 1,2-diphenylethylenediamine. The detection limits, at a signal-to-noise ratio of 5, of the compounds measured in urine are 300 pmol/ml for the two mandelic acids, 2-7 pmol/ml for the other acidic and alcoholic compounds, 12 pmol/ml for L-DOPA and 0.6-2 pmol/ml for the other amino compounds; the corresponding values for plasma samples are 80, 0.5-3, 10 and 0.6-3 pmol/ml, respectively. 相似文献
18.
B. V. Lichitskii A. O. Osipov A. N. Komogortsev A. A. Dudinov M. M. Krayushkin 《Russian Chemical Bulletin》2014,63(2):457-461
A convenient method for the synthesis of earlier unknown substituted derivatives of 4-aryl-7-methyl-4,6-dihydro-3H-pyrano[3,2-c]pyridine-2,5-dione and ethyl 3-(4-hydroxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)-3-arylpropionate was developed based on the multi-component condensation of 4-hydroxy-6-methyl-1H-pyridin-2-one, Meldrum’s acid, and carbonyl compounds. 相似文献
19.
Giuseppe Daidone Salvatore Plescia Jole Fabra 《Journal of heterocyclic chemistry》1980,17(7):1409-1411
Thermal decomposition of the diazonium sulfate derived from N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-aminobenzamide afforded products formulated as 1-phenyl-3-methyl[2]benzopyrano[4,3-c]pyrazol-5-one (yield 10%), 1,4-dimethyl-3-phenylpyrazolo[3,4-c]isoquinolin-5-one (yield 10%), N-methyl-(1-phenyl-3-methylpyrazol-5-yl)-2-hydroxybenzamide (yield 8%) and 4′-hydroxy-2,3′-dimethyl-1′-phenylspiro[isoindoline-1,5′-[2]-pyrazolin]-3-one (yield 20%). Decomposition of the diazonium sulfate derived from N-methyl-(1,3-diphenylpyrazol-5-yl)-2-aminobenzamide gave products formulated as 7,9-dimethyldibenzo[e,g]pyrazolo[1,5-a][1,3]-diazocin-10-(9H)one (yield 8%), 4-methyl-1,3-diphenylpyrazolo[3,4-c]isoquinolin-5-one (yield 7%) and 4′-hydroxy-2-methyl-1′,3′-diphenylspiro[isoindoline-1,5′-[2]pyrazolin]3-one (yield 10%). The spiro compounds 6a,b underwent thermal and acid-catalysed conversion into the hitherto unknown 2-benzopyrano[4,3-c]pyrazole ring system 7a,b in good yield. Analytical and spectral data are presented which supported the structures proposed. 相似文献
20.
A series of 4-(2-keto-substituted)-3,4-dihydro-3-methyl-2H-1,3-benzoxazin-2-ones 1 (Table I) was synthesized by condensation of 3-alkyl-3,4-dihydro-4-hydroxy-2H-1,3-benzoxazin-2-ones 4 with ketones 5 having active alpha hydrogens. In the presence of alcoholic potassium borohydride, compounds 1 underwent reductive transacylation to give 1,3-oxazin-2-one derivatives 3 (Table III, a,b,c). When the other side of the ketone possessed substituents other than hydrogen, there were always also normal reduction products, i.e., secondary alcohols 2 (Table II) in addition to 3. 相似文献