61963-88-0Relevant academic research and scientific papers
Regioselective N-alkylation of some imidazole-containing heterocycles and their in vitro anticancer evaluation
Karaaslan, Cigdem,Doganc, Fatima,Alp, Mehmet,Koc, Asli,Karabay, Arzu Zeynep,G?ker, Hakan
, (2020/01/08)
Imidazole-containing heterocycles: Imidazopyridines, imidazopyrimidines and imidazopyra-zines can exist more tautomeric forms than benzimidazoles. Their regioselectivities were determined for N-alkylations with 4-fluorobenzyl bromide under basic conditions (K2CO3) in DMF. We observed that, regioisomers were mainly formed as a mixture in this reaction and N-benzylation occurs at a higher ratio on six membered heterocycles. Their structural assignments were made with the use of two-dimensional 1H–1H NOE (nuclear overhauser effect spectroscopy, NOESY). Complementary structural information was provided by 2D-HMBC spectra of the compounds. Synthesized compounds were tested for in vitro cytotoxic activities against Human colon cancer cell line (HCT-116) and leukemia cell lines (K562 and HL-60) by MTT test. Among them, imidazopyridine analogue 10, bearing bromine atom at the C-6 position of the pyridine moiety, gave the lowest IC50 value with 6–7 μg/mL against all three cancer cell lines.
Imidazopyridine derivatives, preparation method and pharmaceutical compositions containing same
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Page/Page column 3, (2008/06/13)
Compounds of formula (I): wherein: R1 represents hydrogen, halogen, alkyl, polyhaloalkyl, cyano, nitro, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, R2 represents hydrogen, alkyl, an opt
1H and 13C NMR Studies of Substituted Nitropyridines and Nitrobenzenes
Nudelman, N. S.,Cerdeira, S. B.
, p. 507 - 511 (2007/10/02)
The 1H and 13C NMR spectra of 3-nitro-, 5-nitro- and 3,5-dinitro-2-methoxypyridines have been determined.The results show the preferred cis conformation for the 2-methoxy group, and the importance of steric repulsion between the oxygen atom of this group
Synthesis and analgesic activity of 1,3-dihydro-3-(substituted phenyl)imidazo[4,5-6]pyridin-2-ones and 3-(substituted phenyl)-1,2,3-triazolo[4,5-b]pyridines
Clark,Pessolano,Shen,Jacobus,Jones,Lotti,Flataker
, p. 965 - 978 (2007/10/05)
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.
3-Phenyl,3H 1,2,3 triazolo[4,5-b]pyridines
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, (2008/06/13)
3H-1,2,3-Triazolo[4,5-b]pyridines substituted in the 3-position have utility as analgesic, anti-inflammatory and anti-pyretic agents. They are prepared by diazotization of a 3-amino-2-(substitute) aminopyridine.
