Synthesis of Bioactive Compounds

L-isoleucine methyl ester, L-leucine methyl ester, 3-(dimethylamino)propylamine, 3-(diethylamino)propylamine, benzylhydrazine, 3-bromobenzaldehyde, 3-bromo-1-propanol, MeJA, palladium on carbon, N,N′-dicyclohexylcarbodiimide (DCC), 1-hydroxybenzotriazole (HOBt), N,N-dimethylformamide (DMF), genistein, daidzein, and coumestrol were purchased from Sigma-Aldrich (St. Louis, MO, USA). 2-carboxycinnamic acid, L-valine methyl ester, glycine methyl ester, and anhydrous aluminum chloride (AlCl₃) were obtained from Alfa Aesar Co. (Ward Hill, MA, USA). 2′-hidroxygenistein, dalbergioidin, kievitone, phaseollidin, phaseollinisoflavan, and phaseollin were isolated from a previous work described in [1 (link)]. Dichloromethane (DCM), ethyl acetate (EtOAc), and n-hexane (n-hex) were acquired from Protokimica (Medellín, Colombia) and doubly distilled. Solvents for HPLC were obtained from Merck (Darmstadt, Germany). Ultrapure water (type 1 and 2) was produced by Synergy^® UV and Elix Technology (Millipore, Merck) water purification systems (Darmstadt, Germany). 1-oxo-indane-4-carboxylic acid was prepared according to processes described in [9 (link)] and [13 (link)].