Sodium Cyanate Mediated Synthesis of Sulfonylurea and Sulfonyltriuret from Sulfonyl Chloride and Amine

Hadianawala, Murtuza; Shaik, Althaf; Hasija, Nisha; Vasu, Anuji K.; Datta, Bhaskar

doi:10.1002/slct.201600259

Cited by 5 publications

(4 citation statements)

References 12 publications

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“…Compounds 1 , 2 , and 3 were synthesized according to the reported method [ 68 ]. Sulfonyl chloride (2.4 mmol) was stirred in pyridine (5.0 mmol) for 5 min.…”

Section: Methodsmentioning

confidence: 99%

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Design and Development of Novel Urea, Sulfonyltriurea, and Sulfonamide Derivatives as Potential Inhibitors of Sphingosine Kinase 1

et al. 2020

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Sphingosine kinase 1 (SphK1) is one of the well-studied drug targets for cancer and inflammatory diseases. Recently discovered small-molecule inhibitors of SphK1 have been recommended in cancer therapeutics; however, selectivity and potency of first-generation inhibitors are great challenge. In search of effective SphK1 inhibitors, a set of small molecules have been designed and synthesized bearing urea, sulfonylurea, sulfonamide, and sulfonyltriurea groups. The binding affinity of these inhibitors was measured by fluorescence-binding assay and isothermal titration calorimetry. Compounds 1, 5, 6, and 7 showed an admirable binding affinity to the SphK1 in the sub-micromolar range and significantly inhibited SphK1 activity with admirable IC50 values. Molecular docking studies revealed that these compounds fit well into the sphingosine binding pocket of SphK1 and formed significant number of hydrogen bonds and van der Waals interactions. These molecules may be exploited as potent and selective inhibitors of SphK1 that could be implicated in cancer therapeutics after the required in vivo validation.

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“…Compounds 1 , 2 , and 3 were synthesized according to the reported method [ 68 ]. Sulfonyl chloride (2.4 mmol) was stirred in pyridine (5.0 mmol) for 5 min.…”

Section: Methodsmentioning

confidence: 99%

“…1. General procedure for the synthesis of sulfonyltriurea (Compounds 1, 2, and 3) Compounds 1, 2, and 3 were synthesized according to the reported method [68]. Sulfonyl chloride (2.4 mmol) was stirred in pyridine (5.0 mmol) for 5 min.…”

Section: Synthesismentioning

confidence: 99%

Design and Development of Novel Urea, Sulfonyltriurea, and Sulfonamide Derivatives as Potential Inhibitors of Sphingosine Kinase 1

et al. 2020

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“…As an alternative, starting from sulfonyl chlorides, an intermediate isocyanate is formed with NaOCN that reacts further with amines to sulfonylureas (Figure 23). is single-step reaction is easily accessible for both aliphatic and aromatic sulfonylureas [140].…”

Section: Synthesis Of Sulfonylureasmentioning

confidence: 99%

Carboxylic Acid Bioisosteres in Medicinal Chemistry: Synthesis and Properties

Bredael

Geurs

Clarisse

et al. 2022

Journal of Chemistry

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Lead optimization represents the tedious process of fine-tuning lead compounds from biologically active hits to suitable drug candidates for clinical trials. By chemically modifying a hit structure, an improved compound can be obtained in terms of activity, selectivity, and pharmacokinetic ADME (absorption, distribution, metabolism, and excretion) properties. The carboxylic acid moiety is known to be a crucial functionality in many pharmaceutically active compounds. Despite its common use as a key functionality in drugs, its presence in a lead molecule is often associated with poor pharmacokinetic properties and toxicity. In this literature overview, we discuss how the shortcomings of a carboxylic acid can be circumvented by replacing this functionality with bioisosteres. In this way, the positive aspects of this moiety, such as its activity, for example, by virtue of its capacity to form hydrogen bonds, can be maintained or even improved. To that end, we provide an overview of the most promising carboxylic acid bioisosteres and discuss a selection of synthetic routes towards the main functionalities.

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“…The patent literature [48,49] reports the preparation of aliphatic sulfonylureas by treatment of sulfonyl chloride with sodium cyanate in the presence of base followed by addition of amine. The NaOCN-mediated [50] singlestep reaction works with a variety of sulfonylchlorides 60 and amines 61 making easily accessible both aliphatic and aromatic sulfonylureas 62 including a series of derivatives with effect on the modulation of zinc metalloenzymes (Scheme 21). [51] The reaction of arylsulfonamides 63 with diphenyl carbonate (DPC) in the presence of 4-dimethylaminopyridine (DMAP) produces safe and stable 4-dimethylaminopyridinium carbamoylides 65 via the non-isolable carbamates 64.…”

Section: Syntheses Of Sulfonyl Ureas Based On Disconnection B): N'/c-mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfonylureas

Ventura

Zanirato

2021

Eur J Org Chem

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Sulfonylureas are employed in a variety of applications including use as drugs to treat type II diabetes and as plant growth regulators or herbicides. Traditionally, the synthesis of sulfonylureas has been accomplished either by the treatment of sulfamides with isocyanates in the presence of a base or through sulfonamides conversion into N-sulfonyl isocyanates or N-sulfonyl carbamate derivatives which provide the corresponding sulfonylureas upon treatment with amines. Both approaches are severely limited by the weak nucleophilicity of sulfamides and by the difficulty in synthesizing and handling isocyanate species. Such a drawback could be mitigated by the emergence of protocols establishing the labile electrophilic functional groups in situ so that their coupling with nucleophilic partners takes place in one-pot. Recently, the development of environmentally friendly methods to prepare sulfonylurea containing compounds without using harmful reagents has attracted considerable attention. The aim of the minireview is to explore the different protocols emerged in the literature to generate sulfonylureas giving importance to the reaction mechanisms of crucial synthetic steps.

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Sodium Cyanate Mediated Synthesis of Sulfonylurea and Sulfonyltriuret from Sulfonyl Chloride and Amine

Cited by 5 publications

References 12 publications

Design and Development of Novel Urea, Sulfonyltriurea, and Sulfonamide Derivatives as Potential Inhibitors of Sphingosine Kinase 1

Design and Development of Novel Urea, Sulfonyltriurea, and Sulfonamide Derivatives as Potential Inhibitors of Sphingosine Kinase 1

Carboxylic Acid Bioisosteres in Medicinal Chemistry: Synthesis and Properties

Recent Advances in the Synthesis of Sulfonylureas

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