EurekaMag.com logo
+ Site Statistics
References:
53,869,633
Abstracts:
29,686,251
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on LinkedInFollow on LinkedIn

+ Translate

Synthesis and analgesic activity of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-b]pyridin-2-ones and 3-(substituted phenyl)-1,2,3-triazolo[4,5-b]pyridines



Synthesis and analgesic activity of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-b]pyridin-2-ones and 3-(substituted phenyl)-1,2,3-triazolo[4,5-b]pyridines



Journal of Medicinal Chemistry 21(9): 965-978



In a study of nonsteroidal antiinflammatory and analgesic agents, a series of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-b]pyridin-2-ones-and 3-(substituted phenyl)triazolo[4,5-b]pyridines was prepared. Many of the imidazolones were alkylated on the free nitrogen. In a modified Randall-Selitto analgesic assay, the pain thresholds of both the inflamed and normal foot were elevated. This is not commonly observed with nonsteroidal antiinflammatory agents. The most active compounds were 1,3-dihydro-3[3,4-(methylenedioxy)phenyl]imidazo[4,5-b]pyridin-2-one (I-15) and its N-allyl (I-21) and N-isopropyl (I-121) derivatives. In the triazole series the 3-(2-fluoro- and 2,4-difluorophenyl)triazolo[4,5-b]pyridines (T-1 and T-8) were the best. The imidazole compounds were somewhat superior in analgesic activity to codeine and d-propoxyphene without showing any narcotic characteristics. Some of the compounds also possessed activity against carrageenan-induced foot edema in the rat, so these compounds represent a new class of nonnarcotic analgesic antiinflammatories, capable of producing a greater degree of analgesia than that obtainable with other nonsteroidal antiinflammatory agents.

(PDF emailed within 0-6 h: $19.90)

Accession: 041517412

Download citation: RISBibTeXText

PMID: 309950

DOI: 10.1021/jm00207a023



Related references

A new method for preparation of 1-(4-substituted phenyl)-6-phenyl-2-thiouracils via cyclization of N-(4-substituted phenyl)-N'-3-phenylpropenoylthioureas and Dimroth rearrangement of 2-(4-substituted phenylimino)-6-phenyl-5,6-dihydro-4H-1,3-thiazin-4-ones. Collection of Czechoslovak Chemical Communications 52(9): 2260-2265, 1987

Synthesis, antituberculostatic, antifungal and antibacterial activities of 3-substituted phenyl-6-substituted phenyl-1,2,4-triazolo[4,3-b]pyridazines. Acta Poloniae Pharmaceutica 67(5): 555-562, 2010

Synthesis and QSAR evaluation of 2-(substituted phenyl)-1H-benzimidazoles and [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones. European Journal of Medicinal Chemistry 44(3): 1119-1127, 2008

2-Amino-3-substituted-6-((E)-1-phenyl-2-(N-methylcarbamoyl)vinyl)imidazo-(1,2-a)pyridines as a novel class of inhibitors of human rhinovirus: Stereospecific synthesis and antiviral activity. Journal of Medicinal Chemistry 42(1): 50-59, 1999

Synthesis and biological evaluation of some representative 10-substituted 9,10-dihydro-8H-imidazo-(1,2-a)- and 10-substituted 8H-1,2,4-triazolo-(4,3-a)perimidine derivatives. Chinese Pharmaceutical Journal 45(6): 511-518, 1993

Synthesis and biological evaluation of some representative 10-substituted 9,10-dihydro-8H-imidazo- - and 10-substituted 8H-1,2,4-triazolo- perimidine derivatives. Chinese Pharmaceutical Journal 45(6): 511-518, 1993

Synthesis and antimycobacterial activity of novel 4-5-(substituted phenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazolyl-2-methylphenol derivatives. 2007

Novel 2-(nitrooxy)ethyl 2-(4-(substituted phenyl)-2-((substituted phenyl)amino)thiazol-5-yl)acetate as anti-inflammatory, analgesic and nitric oxide releasing agents: Synthesis and Molecular Docking studies. Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry, 2017

Synthesis and anticonvulsant activity of some 2-(2-{1-[substituted phenyl]ethylidene}hydrazinyl)-4-(4-methoxy-phenyl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile. Journal of Enzyme Inhibition and Medicinal Chemistry 27(6): 825-831, 2013

Synthesis and biological activities of some 2-substituted phenyl-3-(3-alkyl/aryl-5,6-dihydro-s-triazolo- thiadiazol-6-yl)indoles. Indian Journal of Chemistry Section B, Organic including Medicinal 36(8): 707-710, 1997

Synthesis and antifungal activity of 1 3 bis 2 or 4 substituted cinnamoyl or 1 acyl 4 5 dihydro 5 substituted phenyl 1h pyrazol 3 yl phenoxy 2 propanols and related compounds. Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 31(9): 590-594, 1992

A facile iodine(III)-mediated synthesis of 3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridines via oxidation of 2-((3-aryl-1-phenyl-1H-pyrazol-4-yl)methylene)-1-(pyridin-2-yl)hydrazines and their antimicrobial evaluations. Organic and Medicinal Chemistry Letters 1(1): 1-1, 2012

Synthesis and anti inflammatory activity of some new 3 omega substituted phenyl 4 substituted phenyl 5 alkyl alkenyl mercapto 1h 1 2 4 triazoles. Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 20(11): 1017-1018, 1981

Synthesis and in-vitro antifungal activity of 6-substituted-phenyl-2- {[(4'-substituted phenyl-5'-thioxo)-1,2,4-triazol-3-yl]-methyl}-2,3,4,5-tetrahydropyridazin-3-one derivatives. Acta Poloniae Pharmaceutica 65(2): 223-228, 2008

Synthesis and pharmacological activity of 2-(substituted phenyl)-3-(2 or 3-((4-substituted phenyl-4-hydroxy)piperidino)ethyl or propyl)-1,3-thiazolidin-4-ones. Farmaco (Rome) 52(4): 237-241, 1997