Three-component,one-pot synthesis of pyrano[3,2-c]chromene derivatives catalyzed by ammonium acetate: Synthesis,characterization, cation binding,and biological determination

Three-component reaction of arylaldehydes with malononitrile and 4-hydroxycoumarine using CH₃COONH₄ as a catalyst at reflux was used for the synthesis of novel substituted pyrano3,2-c]chromene derivatives. The structure of these compounds was assigned by spectroscopic data such as (IR, ¹HNMR, ¹³CNMR, and mass spectral data). The cation binding properties of chromene derivatives 4a-c towards Cu²⁺, Ni²⁺, and Zn²⁺ were studied in methanol. The results showed that Zn²⁺ is the most complexed in this series of cations, and 4c is best complexed with either Ni²⁺ and Zn²⁺. Antimicrobial properties of new pyrano3,2-c]chromene derivatives are investigated, the compound 4c presents against Micrococcus luteus LB 14110 an MIC value of 0.0185 mg/mL quite better to that of ampicillin (0.0195 mg/mL) used as standard. Concerning acetylcholinesterase inhibition activity (AChEI), compound 4c presents an interesting AChEI activity with an inhibition of 52%.