US 12,491,169 B1
1-naphthalenyl aminoethyl Schiff base and use as a death ligand-1 inhibitor
Amin Osman Elzupir, Riyadh (SA); and Sondos A. J. Almahmoud, Riyadh (SA)
Assigned to IMAM MOHAMMAD IBN SAUD ISLAMIC UNIVERSITY, Riyadh (SA)
Filed by IMAM MOHAMMAD IBN SAUD ISLAMIC UNIVERSITY, Riyadh (SA)
Filed on Apr. 1, 2025, as Appl. No. 19/097,284.
Int. Cl. A61K 31/15 (2006.01)
CPC A61K 31/15 (2013.01) 16 Claims
OG exemplary drawing
 
1. A method of inhibiting the binding of a programmed death-ligand 1 (PD-L1) protein to programmed cell death protein 1 (PD-1), comprising:
contacting the PD-L1 protein with an aminoethyl Schiff base of formula (II) to form a complex of the PD-L1 protein and the aminoethyl Schiff base of formula (II), thereby inhibiting the binding of PD-L1 to PD-1;
wherein the aminoethyl Schiff base of formula (II) is prepared by:
reacting an N-(naphthyl)-ethylenediamine dihydrochloride with an aldehyde of formula (I) in ethanol in the presence of sodium bicarbonate (NaHCO3) to form a reaction mixture; and
refluxing the reaction mixture for 3 hours (h) to 7 h to form the aminoethyl Schiff base of Formula (II);

OG Complex Work Unit Chemistry
wherein Ar is selected from the group consisting of:

OG Complex Work Unit Chemistry
R1, R2, R3, R4, R5, R6, and R7 are hydrogen, nitro, or methoxy.