Rapid Synthesis of Sulfone Derivatives as Potential Antiinfectious Agents.

Curti, Christophe; Laget, M.; Carle, Ann; Gellis, Armand; Vanelle, Patrice

doi:10.1002/chin.200742085

Cited by 21 publications

(24 citation statements)

References 1 publication

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“…Among the derivatives of sulfones, special attention has been drawn to the construction and reactivity of β‐keto sulfones . Some β‐keto sulfones have been reported as effective antimicrobial agents . Moreover, β‐keto sulfones have been reported as key starting materials in the synthesis of several biologically active compounds; for example, β‐keto sulfones was used in the preparation of fused pyrimidine derivatives as potent Aurora‐A kinase inhibitors , and they were used also in the preparation of novel celecoxib analogs as potent anti‐inflammatory agents .…”

Section: Introductionmentioning

confidence: 99%

Novel 4‐Heteroaryl‐antipyrines: Synthesis, Molecular Docking, and Evaluation as Potential Anti‐breast Cancer Agents

Tao

Gomha

Badrey

et al. 2018

Journal of Heterocyclic Chem

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Reaction of 1‐[4‐(1,2‐dihydro‐1,5‐dimethyl‐2‐phenyl‐3‐oxo‐3H‐pyrazol‐4‐yl)‐2‐phenylsulfonyl‐1‐ethanone (1) with phenyl isothiocyanate afforded the 4‐(3‐mercapto‐3‐(phenylamino)‐2‐(phenylsulfonyl)acryloyl)‐1,5‐dimethyl‐2‐phenyl‐1H‐pyrazol‐3(2H)‐one (2). Treatment of compound 2 with hydrazonoyl chlorides 3a–h afforded the corresponding1,3,4‐thiadiazole derivatives 5a–h. Cyclocondensation reaction of compound 2 with the appropriate α‐halo‐compounds 6, 8, 10, 12a,b or 14 (ethyl 2‐chloroacetate, chloroacetonitrile, 1‐chloropropan‐2‐one, 2‐bromo‐1‐phenylethanone, 2‐bromo‐1‐p‐tolylethanone, and 2‐bromoacetyl‐3H‐benzo [f]chromen‐3‐one) afforded the 1,3‐thiazole derivatives 7, 9, 11, 13a,b, and 15, respectively. Coupling of the ketosulphone 1 with the appropriate diazotized 4H‐1,2,4‐triazol‐3‐amine 16 and 2‐aminobenzimidazole 19 afforded triazolo[5,1‐c][1, 2, 4]triazine 18 and benzo[4,5]imidazo[2,1‐c][1, 2, 4]triazine 21, respectively. The structures of the synthesized compounds were confirmed on the basis of their elemental analysis and spectral data and evaluated as potential anti‐breast cancer agents. Moreover, the computational studies using MOE 2014.09 software are confirming the results in biological activity.

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Section: Introductionmentioning

confidence: 99%

Novel 4‐Heteroaryl‐antipyrines: Synthesis, Molecular Docking, and Evaluation as Potential Anti‐breast Cancer Agents

Tao

Gomha

Badrey

et al. 2018

Journal of Heterocyclic Chem

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“…β‐Keto sulfones are attractive synthetic scaffolds owing to their useful biological properties7 and diverse synthetic applications ranging from natural products8 to important organic compounds 9. Consequently, β‐keto sulfones have been described as the target of synthesis in numerous reports 3e,3i,10.…”

Section: Introductionmentioning

confidence: 99%

Inside Cover: Out‐of‐Cell Oxygen Diffusivity Evaluation in Lithium–Air Batteries (ChemElectroChem 12/2014)

Wang

et al. 2014

ChemElectroChem

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“…Alternatively, the sulfur atom can be oxidized, producing the corresponding β‐carbonyl sulfoxides, which are important starting materials for biotransformation to produce chiral β‐hydroxy sulfoxides 4. These types of sulfone derivatives have potential anti‐infective activity 5. Various β‐amino thioether compounds, which could easily be synthesized by functional group interconversion of α‐sulfenylated carbonyl compounds, are reported to be apoptosis promoters;6 their enantiomerically pure isomers are also widely employed as chiral ligands in asymmetric catalysis 7.…”

Section: Introductionmentioning

confidence: 99%

Atom‐Efficient Gold(I)‐Chloride‐Catalyzed Synthesis of α‐Sulfenylated Carbonyl Compounds from Propargylic Alcohols and Aryl Thiols: Substrate Scope and Experimental and Theoretical Mechanistic Investigation

Biswas

Dahlstrand

Watile

et al. 2013

Chemistry A European J

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Gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols showed a wide substrate scope with respect to both propargylic alcohols and aryl thiols. Primary and secondary aromatic propargylic alcohols generated α-sulfenylated aldehydes and ketones in 60–97 % yield. Secondary aliphatic propargylic alcohols generated α-sulfenylated ketones in yields of 47–71 %. Different gold sources and ligand effects were studied, and it was shown that gold(I) chloride gave the highest product yields. Experimental and theoretical studies demonstrated that the reaction proceeds in two separate steps. A sulfenylated allylic alcohol, generated by initial regioselective attack of the aryl thiol on the triple bond of the propargylic alcohol, was isolated, evaluated, and found to be an intermediate in the reaction. Deuterium labeling experiments showed that the protons from the propargylic alcohol and aryl thiol were transferred to the 3-position, and that the hydride from the alcohol was transferred to the 2-position of the product. Density functional theory (DFT) calculations showed that the observed regioselectivity of the aryl thiol attack towards the 2-position of propargylic alcohol was determined by a low-energy, five-membered cyclic protodeauration transition state instead of the strained, four-membered cyclic transition state found for attack at the 3-position. Experimental data and DFT calculations supported that the second step of the reaction is initiated by protonation of the double bond of the sulfenylated allylic alcohol with a proton donor coordinated to gold(I) chloride. This in turn allows for a 1,2-hydride shift, generating the final product of the reaction.

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Rapid Synthesis of Sulfone Derivatives as Potential Antiinfectious Agents.

Cited by 21 publications

References 1 publication

Novel 4‐Heteroaryl‐antipyrines: Synthesis, Molecular Docking, and Evaluation as Potential Anti‐breast Cancer Agents

Novel 4‐Heteroaryl‐antipyrines: Synthesis, Molecular Docking, and Evaluation as Potential Anti‐breast Cancer Agents

Inside Cover: Out‐of‐Cell Oxygen Diffusivity Evaluation in Lithium–Air Batteries (ChemElectroChem 12/2014)

Atom‐Efficient Gold(I)‐Chloride‐Catalyzed Synthesis of α‐Sulfenylated Carbonyl Compounds from Propargylic Alcohols and Aryl Thiols: Substrate Scope and Experimental and Theoretical Mechanistic Investigation

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