An Efficient Method for the Synthesis of Novel N-acylsulfonamides Using Tin (IV) Chloride as Catalysts

Bouchareb, Fouzia; Boufas, Wahida; Cheloufi, Hadjer; Berredjem, Malika; Aouf, Nour‐Eddine

doi:10.1080/10426507.2013.843000

Cited by 14 publications

(9 citation statements)

References 22 publications

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“…[17] Some reports from the literature describe the use of esters as acylating agents of sulfonamides, in the presence of Lewis acids. [20] [18] This methodology was further applied to a wider panel of esters, allowing the synthesis of N-acylsulfonamides of pharmaceutical interest.…”

Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

et al. 2017

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Sulfonamide is a common structural motif in naturally occurring and synthetic medicinal compounds. The rising interest in sulfonamides and N-acyl derivatives is attested by the large number of drugs and lead compounds identified in last years, explored in different fields of medicinal chemistry and showing biological activity. Many acylsulfonamide derivatives were designed and synthesized as isosteres of carboxylic acids, being the characteristics of these functional groups very close. Starting from chemical routes to N-acylsulfonamides, this review explores compounds of pharmaceutical interest, developed as enzymatic inhibitors or targeting receptors.

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Section: Acylation Of Sulfonamidesmentioning

confidence: 99%

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

et al. 2017

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“…Following our efforts to develop novel methods for acylation [24][25][26][27]12 and in continuation of our investigation on the use of ultrasound irradiation to accelerate reactions [28][29][30] , we describe a novel method for acylation the different amines and sulfonamides with acetic anhydride under ultrasonic irradiation, in absence of solvent and catalyst.…”

Section: Resultsmentioning

confidence: 99%

A Novel and Green Method for N-acylation of Amines and Sulfonamides under Ultrasound Irradiation

Bouasla¹,

Bechlem²,

Belhani³

et al. 2017

Orient. J. Chem

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A facile and versatile method for acylation of structurally diverse amines and sulfonamides under focused ultrasonic irradiation in catalyst-free and solvent-free conditions is reported. There are several advantages to this approach such as simple and easier workup conditions, small amount of time and high yielding. The acylation reaction was carried out with acetic anhydride. All structures of synthesized products have been identified by NMR and mass spectroscopy.

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“…In 2014, our group applied a new efficient method for the synthesis of novel N ‐acylsulfonamides, [50] via direct condensation of parent sulfonamide ( 114 ) with ethyl lactate as an acylating agent in the presence of tin (IV) chloride (SnCl 4 ) as a Lewis acid catalyst in acetonitril or toluene. The sulfonamides ( 114 ) were prepared, starting from chlorosulfonyl isocyanate ( 108 ), in three steps (carbamoylation, sulfamoylation, and deprotection) with excellent yields (Scheme 19).…”

Section: Synthesis Of N‐acylsulfonamidesmentioning

confidence: 99%

“…the synthesis of various sulfonamide amino acid (53) and (54). The preparation of N-sulfonylformamidines is reported via the direct condensation of sulfonyl chlorides (50) with p-hydroxybenzoic acid (52) or amino acids (51) in water with Na 2 CO 3 . The sulfonamide derivatives were produced with high yields and purities (Scheme 6).…”

Section: Conflict Of Interestsmentioning

confidence: 99%

Recent Progress in Synthesis of Sulfonamides and N‐Acylsulfonamides, Biological Applications and Their Structure‐Activity Relationship (SAR) Studies

Berredjem,

Bouchareb,

Djouad

et al. 2023

ChemistrySelect

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In recent years, sulfonamide and N‐acylsulfonamide have emerged as prominent areas of scientific research across multiple fields, including chemistry, biology, and medicine. The large number of drugs and lead compounds reported in recent literature evidences the growing interest in these derivatives. Chemists are increasingly intrigued by these molecules owing to their seemingly limitless potential to serve as preferred molecules for numerous applications. Consequently, powerful activities are needed to think of new efficacious therapeutic agents, and it is imperative to discover novel synthetic analogs towards bacterial targets. Advancements in medicinal chemistry have focused on the development of novel sulfonamide and NAS‐bearing analogs that are less harmful, exhibit minimum side‐effort and enhanced dynamic properties. These advanced research areas are currently at the forefront of scientific inquiry. This present review elucidates the contemporary advancements in sulfonamide and N‐acylsulfonamide derivatives, which exhibit diverse and promising pharmacological activities. The different aspects of structure‐activity relationship (SAR) were discussed.

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An Efficient Method for the Synthesis of Novel N-acylsulfonamides Using Tin (IV) Chloride as Catalysts

Cited by 14 publications

References 22 publications

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

A Novel and Green Method for N-acylation of Amines and Sulfonamides under Ultrasound Irradiation

Recent Progress in Synthesis of Sulfonamides and N‐Acylsulfonamides, Biological Applications and Their Structure‐Activity Relationship (SAR) Studies

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