Synthesis and Antimicrobial Activity of Some New Cyanopyridines, Isoxazoles, Pyrazoles, and Pyrimidines Bearing Sulfonamide Moiety

Moustafa, O. S.; Ahmad, Ragaa A.

doi:10.1080/10426500307933

Cited by 26 publications

(14 citation statements)

References 10 publications

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“…Several authors used this reaction successfully in refluxing ethanol and using NaOH [85] or KOH [86][87][88][89][90][91] as base. The reaction of chalcones with hydroxylamine hydrochloride can also be performed in the presence of NaOAc and glacial acetic acid to give 3,5diarylisoxazoles [92,93]. Using the same conditions, the condensation of benzimidazolyl-, benzofuranyl-, indolyl-and quinoxalinyltype chalcones with hydroxylamine hydrochloride provided, respectively, benzimidazolyl- [94], benzofuranyl- [95], indolyl- [96] and quinoxalinyl-isoxazoles [97].…”

Section: Transformation Of Chalcones To Isoxazolesmentioning

confidence: 99%

“…The most common approach for the synthesis of 2-pyrazolines starting from chalcones involves the reaction with hydrazines in refluxing ethanol [93,113,[198][199][200][201][202][203][204][205][206][207][208][209] or methanol [113,125,133,210]. Under these conditions, a large variety of substituents can be found in the synthesis of functionalized 2-pyrazolines such as benzodioxane [211], benzofuran [118,212,213], coumarin [214], indenoquinoxaline [215], naphthalene [125], quinoline [216,217], 1,3-thiazole [218] and thiophene [219][220][221].…”

Section: Transformation Of Chalcones To Pyrazolesmentioning

confidence: 99%

See 1 more Smart Citation

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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Section: Transformation Of Chalcones To Isoxazolesmentioning

confidence: 99%

Section: Transformation Of Chalcones To Pyrazolesmentioning

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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“…[8,17,18] Some noteworthy examples of biologically active drugs containing sulfonamide are shown in Figure 1. [3,8,19] In the light of the immense biological significance of sulfonamides and in the continuity of our research projects on the synthesis of biologically effective compounds, [20][21][22][23] we have undertaken in this study the synthesis of novel sulfonamide derivatives from the readily accessible N-(4-acetylphenyl)benzenesulfonamide (1) [24,25] to evaluate their cytotoxic activities in vitro.…”

Section: Introductionmentioning

confidence: 99%

Convenient synthesis of novel sulfonamide derivatives as promising anticancer agents

El‐Mekabaty

Awad

2019

Journal of Heterocyclic Chem

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Novel sulfonamide derivatives have been synthesized from the readily accessible N‐(4‐acetylphenyl)benzenesulfonamide (1). Condensation of 1 with phenylhydrazine in refluxing ethyl alcohol gave the corresponding phenylhydrazone 2, which was then added to the Vilsmeier‐Haack reagent (POCl3/DMF) to give the 4‐formylpyrazole derivative 3. Fusion of 1 with thiourea in the presence of iodine at 130°C afforded the 2‐aminothiazole derivative 4. Refluxing 1 with an excess of N, N‐dimethylformamide dimethyl acetal furnished the enaminone 5. The chemical reactivity of enaminone 5 toward some nitrogen and carbon nucleophiles has been studied to obtain polyfunctionalized heteroaromatic systems bearing a sulfonamide moiety. Besides, the enaminone 5 undergoes the Gewald reaction and reacts with ethyl cyanoacetate and elemental sulfur in the presence of morpholine to yield the 2‐aminothiophene derivative 18. Moreover, the utility of 5 for the synthesis of 4‐(phenylsulfonamido)benzoic acid (19) was investigated. The synthesized sulfonamides were evaluated for their in vitro cytotoxic activities against two human cell lines, MCF‐7 (breast adenocarcinoma cells) and RPE‐1 (normal retina pigmented epithelium cells). The results revealed that compounds 1‐3, 6‐8, 10, 12b, 18, 19, and 21 have a potent cytotoxic effect on MCF‐7 and less on RPE‐1 cells compared to the positive control doxorubicin®.

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“…Soc. 886 are already known, [35][36][37][38][39] even though their crystal structures have not been elucidated thus far. The nuclear magnetic resonance (NMR) data of two of these compounds (4 and 5) is also new (see Supplementary Information).…”

Section: Introductionmentioning

confidence: 99%

Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity

Castro¹,

Aragão²,

Silva³

et al. 2015

Journal of the Brazilian Chemical Society

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Four sulfonamide-chalcone derivatives were prepared and their crystal structure were elucidated by single-crystal X-ray diffraction technique. They were synthesized by Claisen-Schmidt condensation reaction between N-(4-acetylphenyl)benzenesulfonamide or N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide with benzaldehyde or p-nitrobenzaldehyde. Values of Z' > 1 are found in three compounds as a consequence of conformerism. The chalcone molecular backbones are featured by different levels of planarity in their conformers. Another conformational variability is in its benzenesulfonamide moiety. In the compound came from N-(4-acetylphenyl) benzenesulfonamide and benzaldehyde, there is a rotation of ca. 180° on the bond axis bridging the sulfonamide and chalcone motifs of one conformer if the two others are taken as references. The cytotoxic activity of all compounds synthesized here and of two other related sulfonamide chalcones was also assessed against three cancer cell lines (SF-295, HCT-8 and MDA-MB-435). The para-nitro compounds were the most active ones among all those tested, regardless of substitution pattern in benzenesulfonamide core.

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Synthesis and Antimicrobial Activity of Some New Cyanopyridines, Isoxazoles, Pyrazoles, and Pyrimidines Bearing Sulfonamide Moiety

Cited by 26 publications

References 10 publications

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

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

Convenient synthesis of novel sulfonamide derivatives as promising anticancer agents

Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity

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