共查询到20条相似文献,搜索用时 31 毫秒
1.
F. M. Avotin'sh M. V. Petrova P. V. Pastors A. Ya. Strakov 《Chemistry of Heterocyclic Compounds》1999,35(6):722-728
Anthranilic acid and its 5-bromo and 4-chloro derivatives react with pinanoic and pinonoic acid chlorides to give the corresponding N-acyl derivatives. The pinanoyl derivatives give the corresponding 2-(3-ethyl-2,2-dimethyl-cyclobutylmethyl)-4-(3H)-quinazolinones when refluxed in formamide. Pinanoylanthranilic acid reacts with dicyclohexylcarbodiimide to give 2-(3-ethyl-2,2-dimethylcyclobutylmethyl)benz-3,1-oxazin-4(H)-one and subsequently with hydrazine hydrate to give 3-amino-2-(3-ethyl-2,2-dimethylcyclobutylmethyl)-4(3H)-quinazolinone. Refluxing of the pinanoyl- and pinonoylanthranilic acids with acetic anhydride gives acetylanthranilic acid, and pinonoylanthranilic acid gives 4(3H)-quinazolinone with formamide.Riga Technical University, Riga LV-1658, Latvia; e-mail: marina@osi.lanet.lv. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 811–817, June, 1999. 相似文献
2.
The application of (1S,2S)- or (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propylisothiocyanate as a new chiral derivatizing agent for the resolution of compounds possessing an amino group is described. The reagent is easily accessible in both enantiomeric forms after a simple two-step synthesis. Its applicability was demonstrated on the example of the resolution of a series of alpha-amino acids. The diastereomeric thiourea derivatives produced were separated by reversed-phase high-performance liquid chromatography. The effects of pH, temperature and reagent excess on the derivatization kinetics were investigated, as were the effects of pH and organic modifier on the separation. 相似文献
3.
I Ueda K Ishii K Shinozaki M Seiki H Arai M Hatanaka 《Chemical & pharmaceutical bulletin》1990,38(11):3035-3041
N-Phenoxypropylacetamide derivatives were prepared and tested for antiulcer activity. These compounds exhibited both gastric acid antisecretory and cytoprotective properties. Structure-activity studies led to the identification of N-[3-(3-(1-piperidinylmethyl)phenoxy)propyl]-2-(2-hydroxyethylt hio)acetamide (8), which was selected for further development and clinical evaluation. 相似文献
4.
M Uchida M Chihiro S Morita H Yamashita K Yamasaki T Kanbe Y Yabuuchi K Nakagawa 《Chemical & pharmaceutical bulletin》1990,38(6):1575-1586
A series of 4-substituted 8-[(2-benzimidazolyl)sulfinylmethyl]-1,2,3,4-tetrahydroquinolin es was synthesized and examined for their (H+ + K+)adenosine triphosphatase (ATPase)-inhibitory and antisecretory activities against histamine-induced gastric acid secretion in rats. Many compounds tested were potent inhibitors of (H+ + K+)ATPase. Most compounds showed antisecretory activity. The antiulcer activity against water-immersion stress-induced gastric ulcer, aspirin-induced gastric ulcer and gastric necrosis induced by hydrochloric acid also were tested in the rat. Some of these compounds, in particular, 4-(N-allyl-N-methylamino)-1-ethyl-8-[(5-fluoro-6-methoxy-2-benzimidazoly l) sulfinylmethyl]-1-ethyl-1,2,3,4-tetrahydroquinoline (XVIIx) were found to have potent activity. The structure-activity relationships are discussed. 相似文献
5.
Rajitha Deshineni Ravibabu Velpula Suneetha Koppu Jyothi Pilli Gyanakumari Chellamella 《Journal of heterocyclic chemistry》2020,57(3):1361-1367
A novel series of ethyl-2-(3-((2-(4-(4-aryl)thiazol-2-yl)hydrazono)methyl)-4-hydroxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate derivatives ( 4a-f and 5a-f ) were synthesized by employing one-pot multi-component approach involving ethyl 2-(3-formyl-4-oxy/isobutoxyphenyl)-4-methylthiazole-5-carboxylate, thiosemicarbazide and various phenacyl bromides/3-(2-bromoacetyl)-2H-chromen-2-one/2-(2-bromoacetyl)-3H-benzo[f]chromen-3-onein ethanol in the presence of catalytic amount of acetic acid. The structures of all the synthesized compounds were confirmed with spectral analysis, ie, IR, 1H NMR, 13C NMR and mass spectrometry, and all the compounds were screened for their in vitro antimicrobial activity. 相似文献
6.
F. M. Avotin'sh M. V. Petrova N. N. Tonkikh A. Strakov 《Chemistry of Heterocyclic Compounds》2000,36(11):1326-1328
Beckmann rearrangement of N-[3-(1-hydroxyimino)ethyl-2,2-dimethylcyclobutyl]acetylanthranilic acid, and its 5-bromo and 4-chloro derivatives gives the corresponding N-(3-acetylamino-2,2-dimethylcyclobutyl)acetylanthranilic acids. Treatment of these acylanthranilic acids with formamide gives 2-(3-acetylamino-2,2-dimethylcyclobutyl)methyl-4(3H)-quinazoline and its 6-bromo and 7-chloro derivatives. 相似文献
7.
3-(Pivaloylamino)- and 3-(acetylamino)-4(3H)-quinazolinones react with alkyllithium reagents to give 1,2-addition products in very good yields. Lithiation takes place with LDA and is regioselective at position 2. The lithium reagents thus obtained react with a variety of electrophiles to give the corresponding substituted derivatives in very good yields. Reactions of the lithium reagents with iodine give oxidatively dimerized cyclic structures. 3-(Pivaloylamino)- and 3-(acetylamino)-2-ethyl-4(3H)-quinazolinones and 3-(pivaloylamino)- and 3-(acetylamino)-2-propyl-4(3H)-quinazolinones are lithiated at the benzylic position with LDA. The lithium reagents so produced also react with a variety of electrophiles to give the corresponding 2-substituted-4(3H)-quinazolinone derivatives in very good yields. However, lithiation of 3-(acylamino)-2-(1-methylethyl)-4(3H)-quinazolinones was unsuccessful, as were lithiations of compounds having a diacetylamino group at position 3. The amide groups have been cleaved in good yield under basic or acidic conditions from some of the products to provide access to the free amino compounds. 相似文献
8.
Krasnov V. P. Vigorov A. Yu. Nizova I. A. Grishakov A. N. Evstigneeva N. G. Kodess M. I. 《Russian Chemical Bulletin》2004,53(6):1327-1330
The reaction of dimethyl (2S,4RS)-N-phthaloyl-4-bromoglutamate with 2-methylindoline afforded diastereomeric 4-(2-methylindolin-1-yl)-(S)-glutamic acid derivatives, whose oxidation gave rise to 4-(2-methylindol-1-yl)-(S)-glutamic acid derivatives. 相似文献
9.
(2S,3S)-[3-(2)H1]-4-Methyleneglutamic acid 1a and (2S,3R)-[2,3-(2)H2]-4-methyleneglutamic acid 1b have been synthesised for use in biosynthetic and metabolic studies. 相似文献
10.
A new, efficient, and readily available reagent, methyl 2-((succinimidooxy)carbonyl)benzoate (MSB), for N-phthaloylation of amino acids and amino acid derivatives is described. The phthaloylation procedure is simple and racemization-free and gives excellent results with alpha-amino acids, alpha-amino alcohols, dipeptides, alpha-amino carboxamides, and alpha-amino esters. 相似文献
11.
The metabolites 3 and 4 of 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline dimaleate (AS-2646, 1), a candidate as a gastric antisecretory and antiulcer drug, were synthesized to confirm the proposed structures. The effects of the metabolites 2-4 on ulcer induced by stress were determined. 相似文献
12.
MUHAMMAD Nadeem Arshad HASSAN M.Faidallah ABDULLAH M.Asiri OSMAN I.Osman FAISAL M.S.Aqlan 《结构化学》2019,(3)
Pyridinone derivatives are of great interest in medicinal chemistry where they were found to be potent to various diseases. Their metal complexes added more value to their applications. Here, we have synthesized two 2-pyridinone derivatives(3-cyano-4-(4-hydroxy-3-methoxyphenyl)-6-phenyl-2(1 H)-pyridinone and 3-cyano-4-chlorophenyl-6-(4-tolyl)-2(1 H)-pyridinone) using one-pot multicomponent system. They were well characterized using spectroscopic techniques like nuclear magnetic resonance(NMR-1 H 13 C), Fourier transform infrared(FT-IR) and UV/Vis spectroscopy. The final structures were determined using single-crystal X-ray diffraction technique which helps us to determine their geometries. Density functional theory(DFT) and time-dependent density functional theory(TD-DFT) with suitable basis-sets of calculations have correctly simulated these spectroscopic parameters. The intramolecular charge transfer(ICT) of both substrates has been discussed using natural bond orbital(NBO) technique. Molecular electrostatic potential(MEP) surfaces showed their reactive locations for intermolecular charge transfer. Compared to p-nitroaniline(pNA), both substrates were shown to have substantial molecular hyperpolarizability. 相似文献
13.
K Hino K Kawashima M Oka Y Nagai H Uno J Matsumoto 《Chemical & pharmaceutical bulletin》1989,37(1):110-115
The synthesis of a novel class of antiulcer agents, the substituted 4-phenyl-2-(1-piperazinyl)quinolines, and their pharmacological activities (inhibitory effects on hypothermia induced by reserpine and on gastric ulcers induced by stress or ethanol) are described. These compounds can be classified into three groups (a group predominantly effective on the stress-induced ulcer, one effective on both the stress- and ethanol-induced ulcers, and one selectively effective on the ethanol-induced ulcer), with regard to antiulcer activity. The inhibitory effect on stress-induced ulcer was found to be in close relation to the antagonism of hypothermia. The structure-activity relationships in these compounds are described. Among the compounds, 2-(4-ethyl-1-piperazinyl)-4-phenylquinoline dimaleate (9, AS-2646) showed a potent inhibition of stress-induced ulcer and gastric acid secretion, possively through action on the central nervous system, and it was selected for clinical evaluation. 相似文献
14.
Synthesis of (Z)-4-hydroxytamoxifen and (Z)-2-[4-[1-(p-hydroxyphenyl)-2-phenyl]-1butenyl]phenoxyacetic acid 总被引:1,自引:0,他引:1
The synthesis of (Z)-4-hydroxytamoxifen and (Z)-2-[4-[1-(p-hydroxyphenyl)-2-phenyl]-1-butenyl]phenoxyacetic acid was accomplished using a McMurry reaction as the key step. The perfluorotolyl derivatives of the McMurry products enabled the separation of the minor undesirable geometrical isomer. The methodology proceeds without E,Z isomerization, employs a very mild final debenzylation step compatible with a large array of functional groups, and can be applied to the generation of a variety of 4-hydroxytamoxifen analogues. 相似文献
15.
16.
Synthesis of 2-[[(4-fluoroalkoxy-2-pyridyl)methyl]sulfinyl]-1H- benzimidazoles as antiulcer agents 总被引:1,自引:0,他引:1
Many 2-[[(4-fluoroalkoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazoles were synthesized and tested for anti-secretory, antiulcer, and cytoprotective activities. Most of these compounds were superior to omeprazole in anti-secretory and antiulcer potencies, and especially in protecting the gastric mucosa from ethanol-induced damage. Among these compounds, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl] - 1H-benzimidazole, AG-1749 (lansoprazole) (6f), was selected for further development and clinical evaluation. 相似文献
17.
18.
P. Venkateshwarlu M. V. S. R. K. Chaitanya P. K. Dubey 《Phosphorus, sulfur, and silicon and the related elements》2013,188(6):711-721
Abstract of 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbohydrazide (4) with substituted phenyl isothiocyanates (5) in ethanol under reflux for 30 min gave thiosemicarbazide derivatives 6, which on cyclization in 2N NaOH under refluxing conditions for 1 h resulted in 3-(5-mercapto- 4-phenyl-4H-1,2,4-triazol-3-yl)-1,8-naphthyridin-4(1H)-one (7). Alternatively, 7 could also be prepared from following sequence of reactions, i.e., 4 → 8 → 7. In another sequence of reactions, condensation of 7 with chloroacetic acid in dimethylformamide (DMF) and K2CO3 as a mild base at 120 °C for 2 h resulted in 2-((5-(1,4-dihydro-4-oxo-1,8-naphthyridin-3-yl)-4-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl)acetic acid (10). The latter, on reaction with substituted o-phenylenediamine (11) in 6N HCl for 4 h yielded 3-(5-((1H-benzo[d]imidazol-2-yl)methylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-1,8-naphthyridin-4(1H)-one (12). Alternatively, 12 could also be prepared by reacting 7 with 13 in DMF and K2CO3 as a mild base at 120 °C for 2 h, followed by oxidation with H2O2 resulting in the corresponding sulfonyl derivatives 14. 相似文献
19.
A convenient method of synthesis of substituted and annulated 2-amino-spiro[(3' H)-indol-3',4-(4 H)-pyrans] at mild conditions and in good yields is developed. Three component reaction of wide variety of substituted isatins, cyanoacetic acid derivatives, and carbonyl compounds or phenols gives the target compounds. Forty new spiropyrans were obtained, and their structures were proved by elemental analysis and 1H NMR and IR spectral data. It is shown that the use of a not very large set of starting compounds can lead to the synthesis of a thousand-member 2-amino-spiro[(3' H)-indol-3',4-(4 H)-pyran] library. 相似文献
20.
V. O. Kozminykh D. B. Oborin V. I. Goncharov E. N. Kozminykh 《Chemistry of Heterocyclic Compounds》2007,43(8):978-980
3-Hydroxy-3-(2-oxoethyl)-6-phenyl-2,3-dihydropyridazin-4(1H)-ones were obtained by the reaction of methyl 3-oxo-5-phenylfuran-2(3H)-ylideneacetate
or 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one with benzoic or p-nitrobenzoic isopropylidenehydrazides.
Equilibrium C(5)H and C(5)H2 tautomeric forms were detected in solutions of the 4-chlorophenyl derivatives in DMSO-d6.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1156–1158, August, 2007. 相似文献