2012
DOI: 10.1007/s12272-012-0904-2
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Design, synthesis and pharmacophoric model building of novel substituted nicotinic acid hydrazones with potential antiproliferative activity

Abstract: Novel 6-aryl-2-methylnicotinic acid hydrazides 4a-c and their corresponding hydrazones 5a-c and 6a-i were synthesized. X-ray single crystal diffraction of 6h confirmed the chemical structure of hydrazones 6a-i. Antiproliferative activity of the synthetic compounds was investigated against K562 leukemia cell lines. Variable cell growth inhibitory activities were obtained with IC₅₀ range from 24.99 to 66.78 μM where the compound 6c exhibited the maximum activity. Structure activity relationship analysis has been… Show more

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Cited by 28 publications
(11 citation statements)
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“…Furthermore, 13 C NMR spectra of 5a-o showed signals resonating in the range δ 162.82-165.46 ppm attributable for the carbons of carbonyl groups, while the carbons of the methyl groups appeared in the range δ 23.13-25.52 ppm. Furthermore, we confirmed in a previous study the Z-structure of hydrazones 5a-o under the basics of X-ray single crustal analysis for similar analogue [46].…”
Section: Methodssupporting
confidence: 89%
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“…Furthermore, 13 C NMR spectra of 5a-o showed signals resonating in the range δ 162.82-165.46 ppm attributable for the carbons of carbonyl groups, while the carbons of the methyl groups appeared in the range δ 23.13-25.52 ppm. Furthermore, we confirmed in a previous study the Z-structure of hydrazones 5a-o under the basics of X-ray single crustal analysis for similar analogue [46].…”
Section: Methodssupporting
confidence: 89%
“…The present study is an extension of our ongoing efforts towards developing potent isatin-based anticancer agents [35,36,[45][46][47], utilizing a hybrid pharmacophore approach. In view of the previous findings, we decided to design and synthesize three different set of isatin-pyridine hybrids 5a-o, 8 and 11a-d (Figure 1), with the prime aim of developing potent anticancer agents.…”
Section: Figurementioning
confidence: 99%
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“…The compounds containing arylidene-hydrazide structure may exist as E/Z geometrical isomers about -C= N-double bond and cis/trans amide conformers. 19) According to literature, the presence of single downfield resonating (8.43-8.99 ppm) imine hydrogen signal accounts for formation of E-isomers exclusively, in DMSOd 6 solution, whereas Z-isomer can be stabilized in less polar solvents by an intramolecular hydrogen bond. 20) In the present study, the spectral data were recorded in DMSO-d 6 , and the signal corresponding to the imine hydrogen was observed in the range of 8.…”
Section: Resultsmentioning
confidence: 96%
“…Thus, there is necessity to improve the known analyses methods for this class of compounds or develop new methods. In continuation for our previous work [1924] in the chemistry of the title compounds, certain enaminones 4a–j were synthesized and used as model compounds for this current study.…”
Section: Introductionmentioning
confidence: 99%