Palladium-Catalyzed Synthesis of <i>N</i>-Benzoyl-2-arylethenesulfonamides from [2-(Benzoylsulfamoyl)ethyl]pyridinium Chloride and Aryl Halides

Hirooka, Syuzi; Tanbo, Yuzi; Takemura, Katsuya; Nakahashi, H.; Matsuoka, Toshifumi; Kuroda, Shigeyasu

doi:10.1246/bcsj.64.1431

Cited by 7 publications

(4 citation statements)

References 11 publications

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“…10) Under the same condition, methyl 4-bromobenzoate was reacted with 7 to afford the benzoic acid analogue (4l). Esterification of 4l gave the methyl ester 4k.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Structure-Activity Relationships in a Series of Ethenesulfonamide Derivatives, a Novel Class of Endothelin Receptor Antagonists.

Harada¹,

Kazami²,

Watanuki³

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Endothelin (ET), isolated from the conditioned medium of cultured porcine vascular endothelial cells in 1988, is a highly potent vasoconstrictive 21-amino acid peptide.3) There are three isoforms (ET-1, ET-2, ET-3). ET-1 is the predominant component of the three ET-isopeptides and is derived from precursor big ET-1.4) ET-1 has been believed to be implicated in the pathogenesis of various diseases, largely because of its ability to constrict vascular and nonvascular smooth muscle. 5)Two subtypes of receptors for ETs , termed the ET A receptor and ET B receptor, have been cloned and stably expressed in mammals. ET A receptor appears to exhibit affinity for ET-1 and ET-2 over ET-3, whereas the ET B receptor has nearly equipotent affinity for these three ETs. 6)A number of ET A -selective and ET A /ET B mixed antagonists have been reported for a decade, 7) and some of these ET antagonists are currently in clinical trials.In the previous paper, 8) we described a series of the 2-arylethenesulfonamide derivatives, a novel class of ET A -selective ET receptor antagonists, including the compounds (1a, b) (Fig. 1). Among these, the potassium salt of 1a (YM598 monopotassium) is in clinical trials. Compound 1a showed an IC 50 value of 3.1 nM for the ET A receptor and 1200 nM for the ET B receptor (ET B /ET A ratioϭ390). In the in vivo study, it showed a potent oral inhibitory activity of pressor response to big ET-1-treated rats and excellent pharmacokinetic profiles in rats and dogs. In this paper, we wish to report the investigation of the further details of the structureactivity relationships (SARs) of the 2-phenylethenesulfonamide region in 1a.In the previous study, 8b) replacement of the phenyl group of the 2-phenylethenesulfonmamide moiety in compound 1a with another aryl or heteroaryl groups was explored. This exercise revealed that these modifications were well tolerated in the ET A binding affinity and remarkably led to various ET B /ET A ratios in the 50-820 range. Intrigued by these observations, we became interested in the effect of the further modification of the phenyl group in the phenylethenesulfonamide moiety of 1a on both ET A and ET B binding affinities and the ET A /ET B ratio. We also investigated modification of the ethenyl group in the phenylethenesulfonamide moiety. ChemistryCharts 1 and 2 show the syntheses of alkenesulfonamide derivatives.The starting compound (3) was prepared according to the method reported by Burri and his coworkers.9) Nucleophilic substitution of the pyrimidine derivative 3 with (E)-alkenesulfonamide (4) resulted in the chloropyrimidine (5a-j, mx). The chloropyrimidine 5 was treated with sodium methoxide in N,N-dimethylformamide (DMF) or methanol to give the methoxy analogues (6a, c-j, m-x). Compound 3 was also treated with the methyl ester (4k) to give a mixture of the benzoic acid analogue (5l) and the methyl ester (5k). This mixture was treated with concentrated sulfuric acid in methanol to give 5k as a sole product. Treatment of 5k with sodium methoxide in methanol gave t...

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“…10) Under the same condition, methyl 4-bromobenzoate was reacted with 7 to afford the benzoic acid analogue (4l). Esterification of 4l gave the methyl ester 4k.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Structure-Activity Relationships in a Series of Ethenesulfonamide Derivatives, a Novel Class of Endothelin Receptor Antagonists.

Harada¹,

Kazami²,

Watanuki³

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Finally, styrylsulfonyl derivatives can also be accessed through Heck arylation of vinylsulfonyl derivatives. Compared to the plethora of examples of Heck arylations of acrylates, the analogous couplings of vinylsulfones and vinylsulfonic acid derivatives have hardly been explored , . Generally, successful Heck reactions of these substrates require aryl bromides, activating phosphine ligands such as PPh 3 or occasionally P( o ‐tolyl) 3 , reaction temperatures higher than 100 °C, and reaction times of several hours.…”

Section: Introductionmentioning

confidence: 99%

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

2016

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Arene diazonium salts undergo Matsuda-Heck reactions with vinylsulfonates and -sulfonamides to give styrylsulfonic acid derivatives in high to excellent yields and with high to excellent selectivities. By quantifying the evolution of nitrogen over time in a gas-meter apparatus, the reactivities of ethylvinylsulfonate and the benchmark olefin methyl acrylate were compared for an electron-rich and an -deficient arene diazonium salt. Tertiary sulfonamides react in Matsuda-Heck couplings with high conversions, but require long reaction

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“…p-Methylthiobromobenzene, for example, provides a yield of 77%, entry 1, [210] of coupled product (p-Cl, 93%; p-NH 2 , 73%; p-Me 2 N, 80%; p-AcNH, 83%, p-NO 2 , 73%; p-CN, 98%; p-OMe, 54%; p-CHO, 72%; p-OH, 98%; p-CO 2 Me, 81%; H, 88%) [22] but high yields are also achieved with most ortho-substituted bromobenzenes, such as with 2aminoiodobenzene, which affords the corresponding cinnamic acid in 72% yield, entry 2 [211] (o-NO 2 , 83%; o-OH, 24%; o-CHO, 28%; o-COMe, 89%; o-OAc, 66%; o-CO 2 Me, 69%). [22] High yields and a highly regioselective ␤-arylation are achieved in reactions of aryl halides with acrylic acid, [187] acrylamides, [210] acrylonitrile, [212] ␣,␤-unsaturatd carbonyl compounds, [141] sulfonamides, [213] and vinylphosphonates, [214] and with 1,2-disubstituted alkenes [215] as depicted in entries 3-9. The reactions are preferentially performed in polar nonprotic solvents such as acetonitrile or DMF, and frequently under phase transfer conditions.…”

Section: CI Arylation Of Electron-deficient Alkenesmentioning

confidence: 99%

Intermolecular Heck Reaction: Scope, Mechanism, and Other Fundamental Aspects of the Intermolecular Heck Reaction

Larhed

Hallberg

Handbook of Organopalladium Chemistry for Organic Synthesis

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Palladium-Catalyzed Synthesis of N-Benzoyl-2-arylethenesulfonamides from [2-(Benzoylsulfamoyl)ethyl]pyridinium Chloride and Aryl Halides

Abstract: A new, general synthesis of N-benzoyl-2-arylethenesulfonamides by the reaction of aryl halides including heteroaryl halides with [2-(benzoylsulfamoyl)ethyl]pyridinium chloride in the presence of palladium acetate is described.

Cited by 7 publications

References 11 publications

Synthesis and Structure-Activity Relationships in a Series of Ethenesulfonamide Derivatives, a Novel Class of Endothelin Receptor Antagonists.

Synthesis and Structure-Activity Relationships in a Series of Ethenesulfonamide Derivatives, a Novel Class of Endothelin Receptor Antagonists.

Styrylsulfonates and ‐Sulfonamides through Pd‐Catalysed Matsuda–Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts

Intermolecular Heck Reaction: Scope, Mechanism, and Other Fundamental Aspects of the Intermolecular Heck Reaction

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