%0 Journal Article %1 RN311 %A Polo, E. %A Trilleras, J. %A Ramos, J. %A Galdamez, A. %A Quiroga, J. %A Gutierrez, M. %D 2016 %J Molecules %K acid activity, agents, antioxidant chemistry, discovery, dqcauchile drug green heterocyclic impact, inhibitors, irradiation, microwave microwave, modern organic-synthesis, pyrazoles, synthesis, tetrahydroindazole, %N 7 %R UNSP 903, 10.3390/molecules21070903 %T Efficient Mw-Assisted Synthesis, Spectroscopic Characterization, X-Ray and Antioxidant Properties of Indazole Derivatives %U /brokenurl#<Go to ISI>://WOS:000381509700087 %V 21 %X A small series of tetrahydroindazoles was prepared, starting from 2-acetylcyclohexanone and different hydrazines using reflux and a focused microwave reactor. Microwave irradiation (MW) favored the formation of the desired products with improved yields and shortened reaction times. This is a simple and green method for the synthesis of substituted tetrahydroindazole derivatives. The in vitro antioxidant activity was evaluated using the DPPH and ABTS methods. In these assays, 2-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole (3f) showed moderate DPPH decoloring activity, while 3-methyl-4,5,6,7-tetrahydro-1H-indazole (3a), 3-methyl-2-phenyl-4,5,6,7-tetrahydro-2H-indazole (3b) and 2-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole (3f) were the most active in the ABTS assay. All compounds were well characterized by IR, H-1-, C-13-NMR and GC-MS spectroscopy and physical data, while the structure of 4-(3-methyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)benzoic acid (3e) was also determined by single crystal X-ray analysis.

@article{RN311, abstract = {A small series of tetrahydroindazoles was prepared, starting from 2-acetylcyclohexanone and different hydrazines using reflux and a focused microwave reactor. Microwave irradiation (MW) favored the formation of the desired products with improved yields and shortened reaction times. This is a simple and green method for the synthesis of substituted tetrahydroindazole derivatives. The in vitro antioxidant activity was evaluated using the DPPH and ABTS methods. In these assays, 2-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole (3f) showed moderate DPPH decoloring activity, while 3-methyl-4,5,6,7-tetrahydro-1H-indazole (3a), 3-methyl-2-phenyl-4,5,6,7-tetrahydro-2H-indazole (3b) and 2-(4-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole (3f) were the most active in the ABTS assay. All compounds were well characterized by IR, H-1-, C-13-NMR and GC-MS spectroscopy and physical data, while the structure of 4-(3-methyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)benzoic acid (3e) was also determined by single crystal X-ray analysis.}, added-at = {2019-12-04T03:57:35.000+0100}, author = {Polo, E. and Trilleras, J. and Ramos, J. and Galdamez, A. and Quiroga, J. and Gutierrez, M.}, biburl = {https://www.bibsonomy.org/bibtex/2d32e80b98f68a1fe6843090abbcf122a/dqcauchile}, doi = {UNSP 903, 10.3390/molecules21070903}, interhash = {17249f355837b163308d271570fb23a5}, intrahash = {d32e80b98f68a1fe6843090abbcf122a}, issn = {1420-3049}, journal = {Molecules}, keywords = {acid activity, agents, antioxidant chemistry, discovery, dqcauchile drug green heterocyclic impact, inhibitors, irradiation, microwave microwave, modern organic-synthesis, pyrazoles, synthesis, tetrahydroindazole,}, number = 7, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Efficient Mw-Assisted Synthesis, Spectroscopic Characterization, X-Ray and Antioxidant Properties of Indazole Derivatives}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000381509700087}, volume = 21, year = 2016 }