41082-18-2Relevant 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
The ortho effect in pyridines. Part XI(1). Substituent effects on basicity of 2- and 4-substituted 3-aminopyridines
Rasala, D.
, p. 79 - 84 (2007/10/02)
The substituent effects on the pKa values corresponding to the first protonation site of thirty 2- and 4-substituted 3-aminopyridines have been studied.It was found that the relative localized and delocalized effects are apparently sensitive to the variation of substituent position in the pyridine ring.An interaction of the 2-substituent with the protonation centre has mainly inductive character, whereas, the pKa values of 4-substituted 3-aminopyridines are highly affected by through-resonance.The steric effect was found to be insignificant.Keywords: substituent effects / 2- and 4-substituted 3-aminopyridines / basicity
