Design and development of sulfonylurea derivatives as zinc metalloenzyme modulators

Hadianawala, Murtuza; Datta, Bhaskar

doi:10.1039/c5ra27341b

Cited by 10 publications

(8 citation statements)

References 30 publications

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“…We are interested in the exploration of sulfonylureas as pharmacophores in new medicinal contexts. In this regard, we have recently synthesized a series of novel aliphatic sulfonylurea derivatives by suitably modifying a reported method and used them for their zinc metalloenzyme modulating activity . The sodium cyanate mediated synthesis of sulfonylureas from sulfonyl chlorides and amines has previously been used for the preparation of specific compounds.…”

Section: Resultsmentioning

confidence: 99%

“…We have reported synthesis of several sulfonylurea derivatives using the single‐step reaction methodology described in Scheme . Notably, we were able to access aliphatic sulfonylureas by use of a variety of aliphatic (methyl, ethyl, propyl, isopropyl and cyclohexyl) sulfonyl chlorides and phenylbutylamine.…”

Section: Resultsmentioning

confidence: 99%

“…We have previously used Scheme for synthesis of several aromatic sulfonylureas . The greater yield of aromatic sulfonylureas compared to aliphatic sulfonylureas reflects the greater reactivity of the isocyanate intermediates (see Figure ) vis‐à‐vis aliphatic sulfonyl chlorides compared to tosyl chloride.…”

Section: Resultsmentioning

confidence: 99%

“…We have been pursuing aliphatic sulfonylureas as prospective pharmacophores . In this regard our attempts to use the above mentioned approaches were unsuccessful and spurred us towards the search for an alternative method for the synthesis of sulfonylureas.…”

Section: Introductionmentioning

confidence: 99%

“…This translates to a lack of literature on scope of reaction and reactivity pattern of reaction with different substrates. We have recently reported the successful use of the single‐step reaction from sulfonyl chlorides and amines for preparing sulfonylureas capable of enzyme modulation . In the present work we analyze the scope of sodium cyanate mediated synthesis of sulfonylureas from sulfonyl chlorides and amines.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2016

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Synthetic methods providing access to sulfonylureas are immensely valuable considering the wide usage of sulfonylurea derivatives as hypoglycemic drugs and herbicides. In this work, the scope of a sodium cyanate mediated single-step synthesis of sulfonylureas from amines and sulfonyl chlorides as starting materials has been examined. Success of the single-step reaction in affording desired aliphatic and aromatic sulfonylurea products depends on the combination of suitable nucleophilicity of amines and reactivity of sulfonyl chlorides. In addition to providing access to sulfonylureas, the interplay of reactivities of the amine and sulfonyl chloride is found to result in emergence of specific oligomeric products that are characterized as novel sulfonyltriurets. In effect, the sodium cyanate mediated single-step reaction for synthesis of sulfonylureas also provides a method for synthesis of specific sulfonyltriurets. Electronic effects accompanying the amine and sulfonyl chloride modulate the nature of major product between sulfonylureas and sulfonyltriurets. The sodium cyanate mediated single-step reaction is thus sought to be considered as a method for synthesis of sulfonyltriurets in addition to sulfonylureas.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2016

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Heme Oxygenase Database (HemeOxDB) and QSAR Analysis of Isoform 1 Inhibitors

et al. 2017

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Due to increasing interest in the field of heme oxygenases (HOs), we built a ligand database called HemeOxDB that includes the entire set of known HO-1 and HO-2 inhibitors, resulting in more than 400 compounds. The HemeOxDB is available online at http://www.researchdsf.unict.it/hemeoxdb/, and having a robust search engine allows end users to build complex queries, sort tabulated results, and generate color-coded two- and three-dimensional graphs. This database will grow to be a tool for the design of potent and selective HO-1 or HO-2 inhibitors. We were also interested in virtually searching for alternative inhibitors, and, for the first time in the field of HOs, a quantitative structure-activity relationship (QSAR) model was built using half-maximal inhibitory concentration (IC ) values of the whole set of known HO-1 inhibitors, taken from the HemeOxDB and employing the Monte Carlo technique. The statistical quality suggested that the model is robust and possesses desirable predictive potential. The screening of US Food and Drug Administration (FDA)-approved drugs, external to our dataset, suggested new predicted inhibitors, opening the way for replacing imidazole groups. The HemeOxDB and the QSAR model reported herein may help in prospectively identifying or repurposing new drugs with optimal structural attributes for HO enzyme inhibition.

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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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Design and development of sulfonylurea derivatives as zinc metalloenzyme modulators

Abstract: Sulfonylurea derivatives are zinc metalloenzyme modulators.

Cited by 10 publications

References 30 publications

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

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

Heme Oxygenase Database (HemeOxDB) and QSAR Analysis of Isoform 1 Inhibitors

Recent Advances in the Synthesis of Sulfonylureas

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