Pyridine C-region analogs of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

Ryu, Hyung-Chul; Seo, Sejin; Lee, Jee Young; Ha, Tae Yong; Lee, Sunho; Jung, A Young; Ann, Jihyae; Kim, Sang Hoon; Yoon, Suyoung; Hong, Mannkyu; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Schiene, Klaus; Stockhausen, Hannelore; Christoph, Thomas; Frormann, Sven; Lee, Jeeyeon

doi:10.1016/j.ejmech.2015.02.001

Cited by 13 publications

(3 citation statements)

References 22 publications

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“…The resulting solution was allowed to react, with stirring, for 24 h at a reflux temperature in an oil bath. The resulting mixture was concentrated under vacuum, poured into crushed ice, and filtered by suction; the precipitate was washed with water and dried, yielding 2‐chloro‐6‐phenylnicotinonitrile ( 4a ) as a pale yellow solid, which was used directly without purification 26,27 . The m.p.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and fungicidal activity of novel N‐substituted piperazine‐containing phenylpyridines against cucumber downy mildew

Wang

2022

Pest Management Science

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BACKGROUND Cucumber downy mildew (CDM) is a severe plant disease and affects the yield of cucumber production worldwide. As the resistance toward conventional fungicides is emerging as a ubiquitous issue, it is urgent to discover efficient fungicides with unique structures. RESULTS In this study, a series of novel phenylpyridine derivatives were designed and synthesized. Bioassays revealed that most of these compounds possessed excellent fungicidal activities against CDM. Among the phenylpyridine compounds, 2‐(4‐(4‐(tert‐butyl)benzyl)piperazin‐1‐yl)‐6‐phenylnicotinonitrile (C8) [half‐maximal effective concentration (EC50) = 4.40 mg L−1] displayed the highest activity, which was better than those of the commercial fungicides, such as azoxystrobin (EC50 = 42.77 mg L−1) and flumorph (EC50 = 41.94 mg L−1). Furthermore, the molecular electrostatic potential of high‐activity compound C8 indicated that nitrogen atom of the cyano group on the pyridine ring was in the negative region and may easily form hydrogen bonds and allow for electrostatic interactions with potential receptors. CONCLUSIONS This study demonstrated that the novel N‐substituted piperazine‐containing phenylpyridine derivatives could be further developed as a candidate compound to control CDM.

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Section: Methodsmentioning

confidence: 99%

Design, synthesis, and fungicidal activity of novel N‐substituted piperazine‐containing phenylpyridines against cucumber downy mildew

Wang

2022

Pest Management Science

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“…In this work, we considered another approach to difluorodi(het)arylmethanes, which also relied on the use of (het)aryl difluoro methyl‐substituted building blocks, namely, β‐alkoxyenones of the type 1 [X = (het)aryl, Scheme ]. It should be noted that heterocyclizations of various fluorinated β‐alkoxyenones 1 (X = H, F, Cl, CF 3 , CHF 2 ) were reported in recent publications descri‐bing synthesis of fluoroalkyl‐substituted pyrazoles, isoxazoles, and pyrimidines,, , as well as other heterocycles , . However, no examples of (het)aryl difluoromethyl ‐substituted enones of the type 1 were reported to date.…”

Section: Introductionmentioning

confidence: 99%

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

et al. 2020

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An efficient approach to the preparation of β‐alkoxyenones bearing (het)aryl difluoromethyl substituents is described. The method included acylation of acyclic or cyclic vinyl ethers with (het)aryl difluoroacetyl chlorides. The method worked well for most substrates, except aryl‐substituted derivatives bearing electron‐donating groups in o‐ or p‐positions, and heteroaromatic compounds bearing sufficiently basic nitrogen atom. Synthetic utility of (het)aryl difluoromethyl‐substituted β‐alkoxyenones as CCC bis‐electrophiles was demonstrated by heterocyclizations with common 1,2‐ and 1,3‐bis‐nucleophiles leading to compounds with (het)aryl–CF2–(het)aryl motif, in particular (het)aryl difluoromethyl‐substituted pyrazoles, isoxazoles, and pyrimidines – promising chemotypes for drug discovery.

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“…The 2‐pyridones are prominent intermediates in the synthesis of polycyclic compounds of biological significance, as manifested in the antitumor agents, camptothecin . They are also structural subunits of naturally occurring products such as the heterocyclic annelated pyridone alkaloid Cerpegin, analgesic, antiulcer, and anti‐inflammatory agents . Funiculosine (Fig.…”

Section: Introductionmentioning

confidence: 99%

O‐Glycosylation/Alkylation and Antimicrobial Activity of 4,6‐Diaryl‐2‐Oxonicotinonitrile Derivatives

Haggam

El‐Sayed

Said

et al. 2016

Journal of Heterocyclic Chem

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Pyridine C-region analogs of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists

Cited by 13 publications

References 22 publications

Design, synthesis, and fungicidal activity of novel N‐substituted piperazine‐containing phenylpyridines against cucumber downy mildew

Design, synthesis, and fungicidal activity of novel N‐substituted piperazine‐containing phenylpyridines against cucumber downy mildew

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

O‐Glycosylation/Alkylation and Antimicrobial Activity of 4,6‐Diaryl‐2‐Oxonicotinonitrile Derivatives

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