New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 -1,3-benzoxazine-2(3 )-ones and 6-chloro-3-phenyl-2 -1,3-benzoxazine-2,4(3 )-dithiones

Waisser, Karel; Gregor, Jiřı́; Kubicová, Lenka; Klimešová, Věra; Kuneš, Jiřı́; Macháček, Miloslav; Kaustová, Jarmila

doi:10.1016/s0223-5234(00)00174-4

Cited by 75 publications

(34 citation statements)

References 13 publications

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“…Alternatively, mono bromo derivative 3b was obtained by brominating of the furochromone 1 in glacial acetic acid followed by oxidative cleavage of 9-bromofurochromone 4 with hydrogen peroxide in alkaline medium (Chart 1). Furosalicylanilides 6a-n were prepared from their corresponding furosalicylic acids 3a-c by reaction with the appropriate aromatic amines in chlorobenzene using phosphorus trichloride as a condensing agent [20][21][22] (Chart 2). Furobenzoxazines 8a-f were obtained from the corresponding anilides by reaction with ethyl chloroformate and subsequent cyclization of the resultant esters 7a-f with sodium ethoxide in ethanol (Chart 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anti-inflammatory Activity of Some Benzofuran and Benzopyran-4-one Derivatives

Ragab¹,

Eid²,

Hassan³

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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New series of furosalicylic acids 3a-c, furosalicylanilides 6a-n, furobenzoxazines 8a-f, 1-benzofuran-3-arylprop-2-en-1-ones 12a,b, 6-(aryl-3-oxoprop-1-enyl)-4H-chromen-4-ones 16a-c and 6-[6-aryl-2-thioxo-2,5-dihydropyrimidin-4-yl]-4H-chromen-4-ones 17a-c were synthesized. Anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema model in rats and prostaglandin E 2 (PGE 2 ) synthesis inhibition activity. Some of the tested compounds revealed comparable activity with less ulcerogenic effect than Diclofenac at a dose 100 mg/kg. All the synthesized compounds were docked on the active site of cyclooxygenase-2 (COX-2) enzyme and most of them showed good interactions with the amino acids of the active site comparable to the interactions exhibited by Diclofenac.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Anti-inflammatory Activity of Some Benzofuran and Benzopyran-4-one Derivatives

Ragab¹,

Eid²,

Hassan³

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The studied compounds were synthesized along similar lines as done in previous papers where the synthetic details and analytical data of the studied compounds are described: 2-phenyl-1,3-benzoxazoles [4], 4-(benzylsulfanyl)pyridines [5], and benzoxazines [6]. Acetonitrile Chromasolv (SigmaAldrich) with water content below 2×10 −3 vol% (determined by gas chromatography) was used for the measurements.…”

Section: Determination Of Retention Datamentioning

confidence: 99%

Prediction of retention characteristics of heterocyclic compounds

et al. 2015

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The CORAL software ( http://www.insilico.eu/coral ) was used to build up quantitative structure-property relationships (QSPRs) for the retention characteristics of 93 derivatives of three groups of heterocyclic compounds: 2-phenyl-1,3-benzoxazoles, 4-benzylsulfanylpyridines, and benzoxazines. The QSPRs are one-variable models based on the optimal descriptors calculated from the molecular structure represented by simplified molecular input-line entry systems (SMILES). Each symbol (or two undivided symbols) of SMILES is characterized by correlation weight. The optimal descriptor is the sum of the correlation weights. The numerical data on the correlation weights were calculated with the Monte Carlo method by the manner which provides best correlation between endpoint and optimal descriptor for the calibration set. The predictive ability of the model is checked with the validation set (compounds invisible during building up of the model). The approach has been checked with three random splits into the training, calibration, and validation sets: all models have apparent predictive potential. The mechanistic interpretation of the molecular features extracted from SMILES as the promoters of increase or decrease of examined endpoints is suggested.

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“…They possess various biological activities such as antimicrobial [3], hypolipidacmic [4], antidiabetic [5], anti-inflammatory [6], antimycobacterial [7], antithrombotic [8], antagonism to progesterone receptor [9], antitumor [10], antiviral [11], leucocyte clastase [12] and scrotonin reuptakes [13]. The ground state equilibration of organic compounds was established using spectroscopic data [14].…”

Section: Intrductionmentioning

confidence: 99%

Hammett Spectral Correlations in some Aryl 1,3-Oxazine-4-Thione Derivatives

Thirunarayanan

Sekar

2014

ILCPA

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A series of some aryl 1,3-oxazine-4-thione derivatives have been synthesized by 1-methyl imidazole catalyzed three component one pot synthetic method in room temperature. The purities of these thiones were studied by their physical constants and spectroscopic data. The infrared and 13 C NMR spectral data of CN and CS were correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituent on the spectral data was studied.Keywords: 1,3-oxazine-4-thiones; IR spectra; 13 C NMR spectra; Hammett correlation INTRDUCTIONAryl 1,3-oxazine-4-thiones are pharmaceutical important heterocycles [1,2] [21]. The spatial arrangement of protons such as cis and trans of organic stereo chemical compounds [22] were studied using NMR spectra. Currently chemists and spectroscopic researchers [23][24][25][26][27][28][29] have paid much more interest for correlation of spectral data with Hammett substituent constants. Thirunarayanan and Ravi [30] have studied the effect of substituents of some pyrazoline-1-ethanones. Substituent effects on the spectral group frequencies of 9H-fluorenayl bromides were studied by Thirunarayanan [31]. Sakthinathan et al., have investigated the effect of substituents on naphthyl based pyrazoline derivatives [32]. Sasikala et al.,[22] have evaluated the effect of substituents and antimicrobial activities of some 5-bromo-2-thienyl based pyrazolines. The spectral correlation of infrared and nuclear magnetic resonance spectra of E-imines have been predicted by Sakthinathan et. al. and Suresh et al.,[33,34]. Thirunarayanan and Sekar have investigated the substituent effects on the IR and NMR spectral frequencies of some 3-(3,4-

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New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 -1,3-benzoxazine-2(3 )-ones and 6-chloro-3-phenyl-2 -1,3-benzoxazine-2,4(3 )-dithiones

Cited by 75 publications

References 13 publications

Synthesis and Anti-inflammatory Activity of Some Benzofuran and Benzopyran-4-one Derivatives

Synthesis and Anti-inflammatory Activity of Some Benzofuran and Benzopyran-4-one Derivatives

Prediction of retention characteristics of heterocyclic compounds

Hammett Spectral Correlations in some Aryl 1,3-Oxazine-4-Thione Derivatives

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