Thiophenesulfonamides as endothelin receptor antagonists

Raju, B.; Wu, Chia-Chien; Kois, Adam; Verner, Erik; Okun, Ilya; Stavros, Fiona; Chan, Ming Fai

doi:10.1016/s0960-894x(96)00496-9

Cited by 27 publications

(11 citation statements)

References 12 publications

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“…The first series, prepared as 2-substituted and 3-substituted thiophenes from the corresponding bromo precursors, produced compounds that exhibited fairly good activity and selectivity for ET A . It was also noted that further substitution of the thiophene ring with aryl or alkyl-aryl group at a position adjacent to the sulfonamide changed the overall activity of the resulting molecules [57,58]. However, none was as good as best of benzenesulfonamides and even a biphenyl compound in the same series proved better; Fig.…”

Section: Sulfonamide Antagonistsmentioning

confidence: 98%

Endothelin Receptor Antagonists - An Overview

Dasgupta¹,

Mukherjee²,

Gangadhar³

2002

CMC

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In thirteen years since the appearance of Endothelin (ET) on the international scene, possibility of its involvement in a variety of diseases has attracted the attention of medicinal chemists in search of novel therapeutics for various cardiovascular diseases (CVDs). Discovery of pharmaceutical agents which either block the generation of ET from its precursor or antagonize its binding to cellular receptor, should not only provide means to assess the physiological role of ET, but lead to useful therapy for conditions associated with altered production or responsiveness to ET. In this review article, we have attempted to present in a classified format, the kaleidoscope of ET receptor antagonists that have emerged through structure activity relationship studies using the parent peptide as well as from screening of various compound libraries. By all indications, the variety and range of small molecules that are currently under investigation continues to open up newer opportunities and lures fresh groups of scientists into this research arena. Presently a number of these compounds are in the clinics, being evaluated for their beneficial effects in a range of human pathologies such as essential hypertension and chronic heart failure.

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Section: Sulfonamide Antagonistsmentioning

confidence: 98%

Endothelin Receptor Antagonists - An Overview

Dasgupta¹,

Mukherjee²,

Gangadhar³

2002

CMC

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“…In 2001, the scope and limitations of the Suzuki–Miyaura reaction of 2,3‐dibromothiophene ( 11c ) with boronic acid 19 and ( E )‐6‐hydroxy‐1‐hexenylboronic acid ( 21 ) were analyzed by de Lera et al 30a. (Scheme ), although the site‐selective C‐2 arylation of 11c by palladium‐catalyzed reaction with this boronic acid had previously been reported 30b. It was found that in the presence of a catalytic amount of Pd(PPh 3 ) 4 as the catalyst and K 2 CO 3 as the base ( Method A ), boronic acid 19 (1.1 equiv.)…”

Section: Cross‐coupling Reactions Of Polyhalogenated Five‐membered mentioning

confidence: 99%

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

2012

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The palladium-catalyzed Suzuki-Miyaura reaction of multiply halogenated, electron-rich and electron-deficient heteroarenes is one of the most reliable and environmentally friendly tools for installing a wide range of non-functionalized and functionalized carbon substituents onto heteroaromatic systems with exquisite chemo-and site-selectivity. For substrates with different halogen groups the chemoselectivity of the Suzuki-Miyaura reactions has been found to be dependent on the reactivity difference between the halogens. However, the hardest achievement of selectivity in Suzuki-Miyaura monocouplings involving polyhalogenated heteroarenes with identical halogen atoms has been shown to be dominated by steric and electronic effects and the presence of directing groups at positions neighbouring the reaction sites. Moreover, in the case of symmetrically substituted dihaloheteroarenes with identical halogen atoms, highly selective monocoupling reactions have often been achieved only after a careful optimization of reaction parameters including the catalyst precursor, base, solvent, and the molar ratio between electrophile and organoboron reagent. This critical review with 341 references covers developments on the chemo-and site-selective Suzuki-Miyaura monocoupling reactions of polyhalogenated heteroarenes with different or identical halogen atoms. It also includes the synthesis of polysubstituted heteroarenes, not easily accessible by other means, via consecutive monocoupling reactions and/ or a more synthetically valuable approach involving one-pot polycoupling reactions.

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“…Sulfonamides (R1SO 2 -NHR2) are a common pharmacophore in various biologically active molecules, enzyme inhibitors and receptor antagonists (Lendnicer & Mitscher, 1977;Raju et al, 1996;Raju & Timothy, 1997). This paper reports the structure of N-(4-aminobenzyl)-N,4-dimethylbenzenesulfonamide, (I) ( Fig.…”

Section: Commentmentioning

confidence: 99%