Xanthydrol as a Reagent for the Identification of Sulfonamides

Phillips, R. F.; Frank, Victor S.

doi:10.1021/jo01183a002

Cited by 9 publications

(5 citation statements)

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“…closer examination of _the diazotization and coupling results revealed that the compounds were being decoruposed in the acid solution, liberating soine of the free amine, which accounted for the positive tests. Thus, the disubstituted product with sulfanilamide is correctly represented as N1,N4-dixanthenylsulfanilamide, and not 3,N1-dixanthenylsulfanilamide as previously postulated (7).…”

Section: And Discussionsupporting

confidence: 55%

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Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN¹-monosubstituted sulfanilamides and related compounds

Moskalyk¹,

Chatten²

1967

Can. J. Chem.

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Sulfanilamjdes mere found to undergo alkylation with xanthydrul, yielding either mono-or di-xanthenyl derivatives. The site of substitution, common t o all sulfanilamides having a free p-amino group, was shown t o be the K4-position in the sulfanilamide molecule. Three additional unique reactive sites were observed. Sulfanilamides carrying a thiazole, thiadiazole, or pyridazine substituent in the N1-position were also alkylated on the annular nitrogen atom oi the heterocyclic ring, the reaction having occurred from the imido tautomeric form. Sulfisoxazole (Ik), on the other hand, reacted from the amido form t o give the N1,N4-dixanthenyl derivative. Sulfadimethoxine (Ih) mas substituted a t carbon, as well as a t nitrogen, t o yield N4-xantheny1-1\-'-(2,6-dimethoxy-5-(9-xanthenyl)-4-pyrjmidyl)sulfanilamide.Sulfanilamides possessing pK, values of about 5.5 were found t o be sufficiently acidic t o catalyze their own reaction with xanthydrol. and no external catalqst was necessary. The exceptional ease of formation of the xanthylium ion was postulated t o be associated with the resulting stability of this carbonium ion by virtue of its acquired aromatic character.

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Section: And Discussionsupporting

confidence: 55%

“…Primary benzenoid sulfonamides condense with the reagent to yield the corresponding N-xanthenylsulfonamides (7). The secondary sulfonamide N-ethyl-p-toluenesulfonamide failed to react.…”

Section: Introductionmentioning

confidence: 99%

Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN¹-monosubstituted sulfanilamides and related compounds

Moskalyk¹,

Chatten²

1967

Can. J. Chem.

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“…In this way, the anticipated products, which are useful precursors for benzylation, 8 could be prepared more simply than through conventional reactions involving relatively complex molecules such as xanthones 8 or 9-hydroxyxanthenes. 9 Here we present our results on the facile synthesis of N-(9-xanthyl)-4-toluenesulfonamides via an additioncyclization cascade of salicyl N-tosylimines and silylaryl triflates in the presence of CsF. Scheme 1 Salicyl N-tosylimine, which serves as a reaction partner of arynes As a starting point for our studies, we used salicyl N-tosylimine (2a) to trap the benzyne intermediate generated in situ from 2-(trimethylsilyl)phenyl triflate (1a) in the presence of CsF in acetonitrile at room temperature ( Table 1, entry 1).…”

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confidence: 99%

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confidence: 99%

Efficient Synthesis of N-(9-Xanthyl)-4-Toluenesulfonamides Enabled by an Addition-Cyclization Cascade of Arynes

2013

Synlett

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“…The desired 9-xanthenyl derivatives were obtained following a previously reported procedure describing the condensation of benzenoid sulfonamides with xanthydrol [31]. The solubilization of xanthydrol in glacial acetic acid allows the formation of the xanthylium ion.…”

Section: Chemistrymentioning

confidence: 99%

Xanthene Derivatives Targeting Bacterial Efflux Pumps, Quorum-Sensing, and Biofilm Formation

Maia

Durães

Resende

et al. 2022

DDC

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The rise of multidrug resistance (MDR) bacteria in nosocomial and health-care institutions is widespread and is currently recognized as a major medical challenge. Mechanisms of bacterial resistance, namely, quorum sensing (QS), biofilm formation, and efflux pumps, have been identified as critical biological processes in MDR bacteria. Following previous reports on the activity of phenothiazines against mechanisms of bacterial resistance, in this work we focus on the synthesis of xanthene derivatives aiming to discover phenothiazine bioisosteres with improved activity. Four compounds were obtained from the conjugation of xanthydrol with sulfonamides and aniline and were fully characterized. Their antibacterial activity was assessed considering their minimum inhibitory concentration (MIC) against Gram-positive and Gram-negative strains, efflux pump inhibition, influence on biofilm formation and quorum-sensing (QS) inhibition. It was observed that the MIC of all the tested compounds was above 64 µg/mL The four 9-xanthenyl derivatives obtained, particularly the xanthene sulfonamide derivatives 3b and 3c, showed promising results on QS inhibition with a reduction of pigment production of 48 and 41 mm, and on biofilm formation with a reduction of 78 and 79%, respectively.

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Xanthydrol as a Reagent for the Identification of Sulfonamides

Cited by 9 publications

References 1 publication

Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN¹-monosubstituted sulfanilamides and related compounds

Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN¹-monosubstituted sulfanilamides and related compounds

Efficient Synthesis of N-(9-Xanthyl)-4-Toluenesulfonamides Enabled by an Addition-Cyclization Cascade of Arynes

Xanthene Derivatives Targeting Bacterial Efflux Pumps, Quorum-Sensing, and Biofilm Formation

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Xanthydrol as a Reagent for the Identification of Sulfonamides

Cited by 9 publications

References 1 publication

Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN1-monosubstituted sulfanilamides and related compounds

Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN1-monosubstituted sulfanilamides and related compounds

Efficient Synthesis of N-(9-Xanthyl)-4-Toluenesulfonamides Enabled by an Addition-Cyclization Cascade of Arynes

Xanthene Derivatives Targeting Bacterial Efflux Pumps, Quorum-Sensing, and Biofilm Formation

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Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN¹-monosubstituted sulfanilamides and related compounds

Alkylation by secondary alcohols. I. The reaction of xanthydrol with someN¹-monosubstituted sulfanilamides and related compounds