Abstract
Introduction: 2-Amino-7-hydroxy-4-phenyl-4H-chromene-3-carbonitrile (4) was synthesized through a three-component reaction in ethanol/piperidine solution.
Methods: Synthesis of several new 4H-chromenes (5-14) has been achieved involving various reactions. The structure of these new compounds was confirmed using IR, 1H NMR and 13C NMR, as well as MS spectroscopy.
Results and Conclusion: All newly substituted chromene derivatives displayed potential analgesic and anticonvulsant activities. The structure-activity relationship study revealed that 2-amino-4-phenyl-3-(1Htetrazol- 5-yl)-4H-chromen-7-ol (13) was more beneficial than 8-hydroxy-2-methyl-5-phenyl-3,5-dihydro- 4H-chromeno[2,3-d]pyrimidin-4-one (11), 8-hydroxy-2,5-diphenyl-3,5-dihydro-4H-chromeno[2,3-d]pyrimidin- 4-one (12), and 8-hydroxy-5-phenyl-3,5-dihydro-4H-chromeno[2,3-d]pyrimidin-4-one (14) in terms of analgesic and anti-inflammatory activities.
Keywords: Analgesic, resorcinol, benzaldehyde, hydrazine hydrate, aromatic aldehydes, anti-inflammatory activity.
Graphical Abstract
[http://dx.doi.org/10.1002/chem.201100927] [PMID: 21618299]
[PMID: 15542776]
[http://dx.doi.org/10.2298/JSC120102030S]
[http://dx.doi.org/10.3390/ijms12052822] [PMID: 21686153]
[http://dx.doi.org/10.1016/j.bmcl.2003.08.025] [PMID: 14552749]
[PMID: 20635539]
[http://dx.doi.org/10.1021/jm900146e] [PMID: 19366247]
[http://dx.doi.org/10.1248/cpb.54.391] [PMID: 16508200]
[http://dx.doi.org/10.1016/j.bmcl.2012.04.074] [PMID: 22608389]
[http://dx.doi.org/10.5560/znb.2013-2297]
[http://dx.doi.org/10.1007/s00044-010-9399-x]
[PMID: 18666431]
[http://dx.doi.org/10.15537/smj.2017.4.17061] [PMID: 28397941]
[http://dx.doi.org/10.3390/60600519]
[http://dx.doi.org/10.1016/S0014-827X(00)00097-5] [PMID: 11204946]
[http://dx.doi.org/10.1002/ardp.200800156] [PMID: 19475595]
[http://dx.doi.org/10.3390/ph5070745] [PMID: 24281710]
[http://dx.doi.org/10.1016/S0014-827X(01)01168-5] [PMID: 11829118]
[http://dx.doi.org/10.1016/S0014-827X(02)01263-6] [PMID: 12385521]
[http://dx.doi.org/10.5155/eurjchem.7.2.230-237.1432]
[http://dx.doi.org/10.5155/eurjchem.8.3.240-247.1599]
[http://dx.doi.org/10.2174/1570179416666190719101727] [PMID: 31984914]
[http://dx.doi.org/10.1016/j.bmcl.2005.06.041] [PMID: 16040241]
[http://dx.doi.org/10.3181/00379727-111-27849] [PMID: 14001233]
[http://dx.doi.org/10.1016/j.jep.2003.09.021] [PMID: 14698507]
[http://dx.doi.org/10.1016/0041-008X(79)90153-4] [PMID: 505458]