Novel cannabichromenic acid derivative, preparation method therefor, and composition comprising same for improving cognitive function

A method for preparing a cannabichromenic acid derivative compound represented by Formula 1, comprising:

• reacting (E)-non-3-en-2-one represented by Formula 1-1 with dimethyl malonate represented by Formula 1-2 in an organic solvent to obtain a first compound represented by Formula 1a;
• mixing the first compound obtained above with citral and calcium hydroxide, reacting in an organic solvent to obtain a second compound represented by Formula 2a;
• reacting the second compound obtained above with thiophenol and cesium carbonate to obtain a third compound represented by Formula 3a;
• and
• reacting the third compound obtained above with 1-hydroxybenzotriazole, 1-(3-dimethylaminopropy)-3-ethylcarbodiimide hydrochloride and an amine compound, followed by purification to obtain the cannabichromenic acid derivative compound represented by Formula 1:
• wherein in Formula 1, R1 and R2 are independently hydrogen;
• C1-12 straight or branched alkyl chain;
• C2-12 straight or branched alkenyl chain;
• C2-5 straight or branched alkynyl chain;
• C3-8 cycloalkyl;
• C5-7 aryl;
• aryl C1-4 alkyl;
• 5- to 7-membered heteroaryl having 1 to 3 heteroatom(s) selected from the group consisting of N and S;
• 5- to 7-membered heterocycloalkyl having 1 to 3 heteroatom(s) selected from the group consisting of N, O and S;
• or a fused bicyclic ring in which an aryl ring is fused with a non-aromatic cycloalkyl ring, or
• R1 and R2 are linked together to form a 5- to 7-membered non-aromatic heterocyclic ring having N linked to R1 and R2 and further having 0 to 2 heteroatoms selected from the group consisting of N and S,
• wherein the non-aromatic heterocyclic ring formed with R1 and R2 may be fused with an aryl ring to form a fused bicyclic ring, R1 and R2 may be substituted with one or more Ra, and Ra is C1-5 alkyl, halogen-substituted aryl, halogen-substituted heteroaryl, oxido, hydroxy, hydroxyalkyl, mercapto, alkylsulfonyl, halogen or butoxycarbonyl.