Synthesis and molluscicidal evaluation of some new pyrazole, isoxazole, pyridine, pyrimidine, 1,4-thiazine and 1,3,4-thiadiazine derivatives incorporating benzofuran moiety

Shehry, Mohamed F. El; Swellem, R. H.; Abu-Bakr, Sherifa M.; El-Telbani, Emad M.

doi:10.1016/j.ejmech.2010.07.043

Cited by 30 publications

(18 citation statements)

References 14 publications

(13 reference statements)

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“…[31] The progress of the reaction and the purity of the compounds were routinely monitored on TLC by pre-coated aluminum silica gel 60F254 thin layer plates obtained from Merck (Germany) eluting with petroleum ether/ethyl acetate. The yields of all products were not optimized.…”

Section: Methodsmentioning

confidence: 99%

“…The fact that α,β-unsaturated carbonyl compounds are push-pull olefins, and Michael acceptors permits them as adaptable intermediates in the synthesis of many azole and azine molecules. [31] Changes in their structure have offered a high degree of diversity that has proven useful for the development of new therapeutic agents having improved potency and lowered toxicity. Based on the above considerations and in continuation of our research on biologically potent heterocyclic derivatives, [32][33][34][35][36][37][38] herein, we report the synthesis, structural elucidation and antidiabetic activity of some new azoles and azines prepared from commercially available reagents.…”

Section: Introductionmentioning

confidence: 99%

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Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

2017

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Various interesting heterocycle skeletons were synthesized via Michael type addition reaction with 1,2; 1,3-bidentate nitrogen and carbon nucleophiles. Cycloaddition of different α,β-unsaturated systems afforded bromopyrimidinone 3/5, bromothiazine 4 and bromopyrazole 6a/6b pyrazole-1-carboxylate 8, pyridinylmethanone 9, nicotinonitrile 10, pyrazolopyridine 11a/11b, pyran-3-carbonitrile 12/13, chromenopyridine 14 and N-butyrylpyrazolyl-1-butanone 15 derivatives. The structures of the synthesized compounds were elucidated based on IR, NMR and mass spectral analyses. Group of the newly synthesized compounds were screened for their anti-diabetic activities, whereas compounds 8 and 11b exhibited promising anti-diabetic activities at micro molar concentration against α-glucosidase inhibitor with IC50 values ranging between 13.80-500 μM. On the other hand compound 10 showed a week effect as compared to the standard anti-diabetic agent.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

2017

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“…This one-pot reaction involves an oxidative cyclocondensation followed by an electrophilic hydroarylation [105]. Instead of 3,5-diarylisoxazoles, a series of 3,5-diaryl-2isoxazoline derivatives is attained from the reaction of chalcones with hydroxylamine hydrochloride with minor modifications in an appropriate solvent (usually a protic solvent such as ethanol and methanol) and using a catalytic amount of a base such as KOH [102,[106][107][108][109], NaOH [102][103][104][105][106][107][108][109][110][111][112][113][114][115] and NaOAc [116][117][118][119]. Replacing the solvent by acetic acid, a series of 2-isoxazolines arises from the reaction of hydroxylamine hydrochloride in the presence of NaOAc with chalcone-based compounds bearing pyrrole [120], methylenebisthiazolidinone [121] and benzimidazole [122] moieties.…”

Section: Transformation Of Chalcones To Isoxazolesmentioning

confidence: 99%

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Albuquerque¹,

Santos²,

Cavaleiro³

et al. 2014

COC

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Chalcones belong to the flavonoid family which constitutes one of the major classes of naturally occurring oxygen heterocyclic compounds. The ,-unsaturated carbonyl system of chalcones possesses two electrophilic reactive centers allowing them to participate in addition reactions via attack to the carbonyl group (1,2-addition) or involving the-carbon (1,4-conjugate addition), leading to the synthesis of promising bioactive heterocyclic compounds. The purpose of this review is to present a systematic survey of the most recent literature that uses chalcones in the synthesis of biologically active 5-and 6-membered nitrogen heterocycles such as pyrroles, indoles, isoxazoles, imidazoles, pyrazoles, indazoles, triazoles, tetrazoles, pyridines and pyrimidines. Efficiency, easy-to-handle and cheap reagents, alternative heating conditions and greener protocols will be highlighted. In this review we will cover the literature since the beginning of the 21 st century in more than 400 publications.

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“…They are the main precursors for the synthesis of a wide range of a biologically active heterocyclic compounds such as pyrazoles [1][2][3][4][5], isoxazoles [4,5], oxazines [6], pyrimidines [7,8], thiazine derivatives, and many other heterocycles [9]. Chalcone substructure is also well-known for the biosynthesis of flavonoids and isoflavonoids that have high therapeutic and preventive potential of many diseases [10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of new 3,5-disubstituted-4,5-dihydro-1H-pyrazole and their carbothioamide derivatives

Ibrahim

2015

Eur. J. Chem.

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A new series of substituted pyrazolines (6-10) were synthesized in moderate to excellent yield by treatment of chalcones (1-5) with hydrazine monohydrate. The carbothioamide compounds (11)(12)(13)(14) were obtained in 65% to quantitative yield by treatment of chalcones (2, 4, and 5) either with thiosemicarbazide or with phenylisothiocyanate. All new compounds were characterized by various spectroscopic methods such as 1 H NMR, 13 C NMR, DEPT, COSY, HSQC spectroscopy, elemental analysis, and high resolution mass spectroscopy. The obtained compounds are currently under biological investigations, and the results will be reported elsewhere. KEYWORDS

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Synthesis and molluscicidal evaluation of some new pyrazole, isoxazole, pyridine, pyrimidine, 1,4-thiazine and 1,3,4-thiadiazine derivatives incorporating benzofuran moiety

Cited by 30 publications

References 14 publications

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Synthesis and characterization of new 3,5-disubstituted-4,5-dihydro-1H-pyrazole and their carbothioamide derivatives

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