A series of eleven ethoxysubstituted chalcones (E1-E11) were synthesized and investigated for their inhibitory potential towards human recombinant monoamine oxidase A and B (hMAOÀ A and hMAOÀ B, respectively) and acetylcholinesterase (AChE). IC 50 values of 4.63 � 0.15 and 0.053 � 0.003 μM were obtained for MAOÀ A and MAOÀ B, respectively, by the most interesting compound (2E)-1-(4-ethoxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one (E7), and it was characterized by a high selectivity index (SI = 87.4) for MAOÀ B. Inhibitions by E7 against MAOÀ A and MAOÀ B were recovered (75.9 and 74.5%, respectively) to near the levels of reversible references (77.1 and 77.4%, respectively). The inhibition modes of E7 for MAOÀ A and MAOÀ B were competitive with K i values of 2.65 � 0.064 and 0.011 � 0.0011 μM, respectively. Compounds (2E)-1-(4ethoxyphenyl)-3-(4-ethylphenyl) prop-2-en-1-one (E10) and (2E)-1-(4-ethoxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (E11) showed good inhibitions against AChE with IC 50 values of 2.86 � 0.041 and 3.23 � 0.0073 μM, respectively. A combined molecular docking/MM-GBSA approach was used that employed quantum mechanics (QM) partial charges; this technique revealed the molecular rationale behind the observed MAOÀ B selectivity for this molecular series. Taken together, these results indicate that E7 is a potent, selective and reversible competitive inhibitor of MAOÀ B with moderately potent AChE inhibitory activity that has potential as a multitargeting drug

No abstract

The title compounds were synthesized by condensation of 3-acetyl chromen-2-one with benzaldehyde in presence of alcoholic sodium hydroxide to get intermediate 3-(3-phenyl acryloyl) chromen-2-one, which were further treated with hydrazine hydrate to get 3-(5-phenyl-4,5-dihydro-1H-pyrazol-3-yl) chromen-2-one. The latter were refluxed with various amino compounds and various aldehyde derivatives on water bath for 5 h to afford title compounds. All the compounds were tested for their antibacterial and antifungal activities by the cup plate method.

No abstract