Balanced AT1 and AT2 angiotensin II antagonists. I. New orally active 5-carboxyl imidazolyl biphenyl sulfonylureas

Deprez, Pierre; Heckmann, Bertrand; Corbier, Alain; Vevert, Jean-Paul; Fortin, M.; Guillaume, Jacques

doi:10.1016/0960-894x(95)00478-c

Cited by 18 publications

(7 citation statements)

References 17 publications

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“…The sulfonylurea group is common to many compounds that have been recognized for their biological activities. These include antihypertensive,47 antineoplastic48 and antibacterial49 drugs, in addition to some compounds that exhibit herbicidal action 50. Notably, sulfonylurea ( SU ) drugs have been used extensively in the treatment of non-insulin dependent diabetes mellitus.…”

Section: Resultsmentioning

confidence: 99%

Experiment stands corrected: accurate prediction of the aqueous pK_avalues of sulfonamide drugs using equilibrium bond lengths

2019

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Section: Resultsmentioning

confidence: 99%

Experiment stands corrected: accurate prediction of the aqueous pK_avalues of sulfonamide drugs using equilibrium bond lengths

2019

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“…The sulfonylurea group is common to many compounds that have been recognized for their biological activities. These include antihypertensive 46 , antineoplastic 47 and antibacterial 48 drugs, in addition to some compounds that exhibit herbicidal action 49 . Notably, sulfonylurea (SU) drugs have been used extensively in the treatment of non-insulin dependent diabetes mellitus.…”

Section: Models: Sulfonylureas (Su)mentioning

confidence: 99%

Experiment Stands Corrected: Accurate Prediction of the Aqueous pKa Values of Sulfonamide Drugs Using Equilibrium Bond Lengths

Caine

Bronzato

Popelier

2019

Preprint

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We show here for the first time that strongly correlated linear relationships exist between equilibrium bond lengths of the sulfonamide group and aqueous pKa values. Models are constructed for three variants of the SO2NHR group: primary benzene sulfonamide derivatives (e.g. diuretic drugs furosemide and hydrochlorothiazide), N-phenyl substituted 4-amino-N-phenylbenzenesulfonamide analogues (e.g. the sulfa antibiotic sulfadiazine) and phenylsulfonylureas (e.g. insulin secretogogue, glimepiride). In the context of these compounds, we present solutions to some of the more complex challenges in pKa prediction: (i) prediction for multiprotic compounds, (ii) predicting macroscopic values for compounds that tautomerize, and (iii) quantum chemical pKa prediction for compounds with more than 50 atoms. Using bond lengths as a powerful descriptor of ionization feasibility, we also identify that literature values for drug compounds celecoxib, glimepiride and glipizide are inaccurate. Our newly measured experimental values match our initial predictions to within 0.26 pKa units, whereas previous values were found to deviate by up to 1.68 pKa units. For glimepiride, our corrected value denotes a percentage of ionization at intracellular pH, which is only now in excellent agreement with its known therapeutic efficacy. We propose that linear relationships between bond lengths and pKa should emerge for any set of congeners, thus providing a powerful method of pKa prediction obviating the need for thermodynamic cycles.

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“…In 2011, a NaI‐catalyzed direct condensation of sulfonamide and formamide was demonstrated by us to give various N ‐sulfonylamidines using TBHP as the oxidant, which are the core framwork in many bioactive natural products and pharmacophores, and also serve as useful synthetic intermediates or as efficient ligands in coordination chemistry . This methodology was applied to a series of sulfonamides and formamides and the corresponding N ‐sulfonylamidines were isolated in moderate to excellent yields (Scheme ).…”

Section: (Hypo)iodite Processmentioning

confidence: 99%

Combination of Tetrabutylammonium Iodide (TBAI) with tert‐Butyl Hydroperoxide (TBHP): An Efficient Transition‐Metal‐Free System to Construct Various Chemical Bonds

Chen

Zhang

et al. 2018

The Chemical Record

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In this account, we describe our recent progress on transition-metal-free-catalyzed cross-coupling reactions using tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant. A rich variety of important organic compounds including α-acyloxy ethers, tert-butyl peresters, allylic esters, amides, α-amino nitriles, fully substituted pyrazoles, N-sulfonyl formamidines, α-amino acid esters, cyanomethyl esters, N-nitrosamines, and 3-acyloxy-2,3-dihydrobenzofurans have been successfully achieved in high chemoselectivity. Mechanistic studies suggested that TBAI could decompose TBHP to BuO and BuOO or be oxdized to (hypo)iodite by TBHP.

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Balanced AT1 and AT2 angiotensin II antagonists. I. New orally active 5-carboxyl imidazolyl biphenyl sulfonylureas

Cited by 18 publications

References 17 publications

Experiment stands corrected: accurate prediction of the aqueous pK_avalues of sulfonamide drugs using equilibrium bond lengths

Experiment stands corrected: accurate prediction of the aqueous pK_avalues of sulfonamide drugs using equilibrium bond lengths

Experiment Stands Corrected: Accurate Prediction of the Aqueous pKa Values of Sulfonamide Drugs Using Equilibrium Bond Lengths

Combination of Tetrabutylammonium Iodide (TBAI) with tert‐Butyl Hydroperoxide (TBHP): An Efficient Transition‐Metal‐Free System to Construct Various Chemical Bonds

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Balanced AT1 and AT2 angiotensin II antagonists. I. New orally active 5-carboxyl imidazolyl biphenyl sulfonylureas

Cited by 18 publications

References 17 publications

Experiment stands corrected: accurate prediction of the aqueous pKavalues of sulfonamide drugs using equilibrium bond lengths

Experiment stands corrected: accurate prediction of the aqueous pKavalues of sulfonamide drugs using equilibrium bond lengths

Experiment Stands Corrected: Accurate Prediction of the Aqueous pKa Values of Sulfonamide Drugs Using Equilibrium Bond Lengths

Combination of Tetrabutylammonium Iodide (TBAI) with tert‐Butyl Hydroperoxide (TBHP): An Efficient Transition‐Metal‐Free System to Construct Various Chemical Bonds

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Experiment stands corrected: accurate prediction of the aqueous pK_avalues of sulfonamide drugs using equilibrium bond lengths

Experiment stands corrected: accurate prediction of the aqueous pK_avalues of sulfonamide drugs using equilibrium bond lengths