1,4-Diaryl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acids as endothelin receptor antagonists

Mederski, Werner W. K. R.; Osswald, M.; Dorsch, Dieter; Christadler, Maria; Schmitges, C.‐J.; Wilm, Claudia

doi:10.1016/s0960-894x(97)00319-3

Cited by 40 publications

(9 citation statements)

References 13 publications

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“…Based on their receptor binding abilities in rat iorta and porcine kidney membranes, it was concluded that compound 180 exhibited a balance affinity in sub micromolar range [198]. One of the strategies to combat diseases associated with central nervous system is to design modulators of maxi-K channels [192], in neurons and smooth muscle cells [194].…”

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confidence: 99%

Recent Advances in Coumarins and 1-Azacoumarins as Versatile Biodynamic Agents

Kulkarni¹,

Kulkarni²,

Chao³

et al. 2006

CMC

222

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Coumarins, also referred as benzopyran-2-ones, and their corresponding nitrogen counterpart, 1-azacoumarins also referred to as carbostyrils, are a family of nature-occurring lactones and lactams respectively. The plant extracts containing coumarin-related heterocycles, which were employed as herbal remedies in early days, have now been extensively studied for their biological activities. These investigations have revealed their potentials as versatile biodynamic agents. For example, coumarins with phenolic hydroxyl groups have the ability to scavenge reactive oxygen species and thus prevent the formation of 5-HETE and HHT in the arachidonic pathway of inflammation suppression. Recent in vivo studies have revealed the role of coumarins in hepatotoxicity and also in depletion of cytochrome P450. Similarly 1-azacoumarins which is part of quinoline alkaloids, are known for their diverse biological activity and recently, a 6-functionalized 1-aza coumarins are undergoing human clinical trials as an orally active anti-tumor drug in view of its farnesyl protein-inhibiting activity in the nanomolar range. Furthermore, several synthetic coumarins with a variety of pharmacophoric groups at C-3, C-4 and C-7 positions have been intensively screened for anti-microbial, anti-HIV, anti-cancer, lipid-lowering, anti-oxidant, and anti-coagulation activities. Specifically, coumarin-3-sulfonamides and carboxamides were reported to exhibit selective cytotoxicity against mammalian cancer cell lines. The C4-substituted aryloxymethyl, arylaminomethyl, and dichloroacetamidomethyl coumarins, along with the corresponding 1-azacoumarins, have been demonstrated to be potential anti-microbial and anti-inflammatory agents. To expand the structural diversity of synthetic courmarins for biological functions, attempts have also been made to attach a chloramphenicol side chain at C-3 position of courmarin. In addition, the bi- and tri-heterocyclic coumarins and 1-azacoumarins with benzofuran, furan and thiazole ring systems along with biocompatible fragments like vanillin have shown remarkable potency as anti-inflammatory agents in animal models. Photobiological studies on pyridine-fused polycyclic coumarins have highlighted their potential as thymine dimer photosensitisers and the structurally related compounds of both coumarin and carbostyrils have also been found to act via the DNA gyrase pathway in their anti-bacterial activity. Apart from the above works, the present review also addresses the potential roles of coumarins and carbostyrils as protease inhibitors, or fluorescent probes in mechanistic investigation of biochemical pathways, and their application for QSAR in theoretical studies. Though 1-Azacoumarins have received less attention as compared to coumarins in the literature, an attempt has been made to compare both the systems at various stages, so that it can spark new thoughts on synthetic methodologies, reactivity pattern and biological activities.

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mentioning

confidence: 99%

Recent Advances in Coumarins and 1-Azacoumarins as Versatile Biodynamic Agents

Kulkarni¹,

Kulkarni²,

Chao³

et al. 2006

CMC

222

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“…Several rational variations of known antagonists were reported in the recent years. 1,4-Diaryl-2-oxo-1,2-dihydroquinoline-3-carboxylic acids were discovered as natural extension of an indole compound [99], benzapine-2-one as well as dibenzodiazepine-10-acetic acid derivatives were designed from BQ-123, 4,5-dihydro-1H-benz[g]indazole-3-carboxylic acid derivatives were potent ET antagonists [100], and sulfonylamido derivative of indole-6-carboxylic acid [101] has been described; Fig. (21).…”

Section: Nonpeptide and Nonsulfonamide Anta-gonistsmentioning

confidence: 99%

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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“…[2] They are also beneficial intermediates in organic synthesis. [3] In addition, quinolin-2(1H)-ones have attracted considerable attentions because of their intriguing broad range of biological activities as endothelin receptor antagoists, [4] p38aMAP kinase inhibitors, [5] angiotensin II receptor antagonists, [6] antitumor agents, [7][8] and CDK5 inhibitor. [9] Nybomycin and deoxynybomycin, as promising antibiotics possess quinolin-2(1H)-ones and are found to exhibit activity against bacteria.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel 1,3‐Cyclohexadiene Derivatives Bearing 2‐Oxo‐Quinoline Moiety via a 4‐CR Strategy**

2021

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Herein, we report the first example of green synthesis of hybridized 1,3‐cyclohexadiene (1,3‐CHD) scaffolds in moderate to excellent yields. The catalyst‐free sequential four‐component reaction of 2‐chloroquinoline‐3‐carbaldehydes, 1‐phenyl‐2‐(1,1,1‐triphenyl‐λ5‐phosphanylidene)ethan‐1‐one, ethyl acetoacetate and primary amine in ethanol afforded tetrasubstituted 1,3‐cyclohexadienes bearing 2‐oxo‐1,2‐dihydroquinoline moiety during 4 hours. The structure of the synthesized products was determined via X‐ray analysis. This approach is characterized by its operational simplicity, readily available precursors, green solvent, mild conditions, and moderate to excellent yields.

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1,4-Diaryl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acids as endothelin receptor antagonists

Cited by 40 publications

References 13 publications

Recent Advances in Coumarins and 1-Azacoumarins as Versatile Biodynamic Agents

Recent Advances in Coumarins and 1-Azacoumarins as Versatile Biodynamic Agents

Endothelin Receptor Antagonists - An Overview

Synthesis of Novel 1,3‐Cyclohexadiene Derivatives Bearing 2‐Oxo‐Quinoline Moiety via a 4‐CR Strategy**

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