authors |
Eddahmi, M; Moura, NMM; Bouissane, L; Faustino, MAF; Cavaleiro, JAS; Paz, FAA; Mendes, RF; Figueiredo, J; Carvalho, J; Cruz, C; Neves, MGPMS; Rakib, E |
nationality |
International |
journal |
CHEMISTRYSELECT |
author keywords |
Alkylation; Cancer; Knoevenagel Condensation; Nitroindazolylacetonitriles; Pinner Reaction |
keywords |
INDAZOLE DERIVATIVES; INHIBITORS; POTENT; OPTIMIZATION; SOLUBILITY; SYNTHASE |
abstract |
The versatility of N-methyl-nitroindazolylacetonitriles as templates for further modifications was evidenced by their successfully alkylation with a series of alkyl halides using DBU as base affording the monoalkylated derivatives in high yields. Another synthetic strategy used to modify the nitroindazolylacetonitrile derivatives was the Knoevenagel condensation with a series of aldehydes in the presence of piperidine; such condensation allowed the preparation of the desired products in good to excellent yields. The reaction of a series of nitroindazolylacetonitriles with salicylaldehyde showed to be an efficient and fast methodology to prepare chromenone-imine-indazoles (83-92%), which by acid hydrolysis were converted into the corresponding chromenone-indazole derivatives (88-94%). The structures of derivatives 8 h, 8 l and 10 were unequivocally confirmed by single crystal X-ray diffraction. The drug-likeness properties of the compounds were evaluated in silico and none of the tested nitroindazolylacetonitriles violated the Lipinski's rule of five. The antiproliferative activity against human cervical cancer cells (HeLa) and normal human dermal fibroblasts was evaluated by MTT assay and revealed that compounds 7 b, 8 d and 14 a are those who presented higher antiproliferative effect against HeLa cancer cells. |
publisher |
WILEY-V C H VERLAG GMBH |
issn |
2365-6549 |
year published |
2019 |
volume |
4 |
issue |
48 |
beginning page |
14335 |
ending page |
14342 |
digital object identifier (doi) |
10.1002/slct.201904344 |
web of science category |
Chemistry, Multidisciplinary |
subject category |
Chemistry |
unique article identifier |
WOS:000505279300040
|
ciceco authors
impact metrics
journal analysis (jcr 2019):
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journal impact factor |
1.811 |
5 year journal impact factor |
1.835 |
category normalized journal impact factor percentile |
37.571 |
dimensions (citation analysis):
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altmetrics (social interaction):
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