Abstract
Abstract 3-Bromo-5-chloro-N-(2-chlorophenyl)-2-hydroxybenzamide (BCNCPB–OH) was synthesized as a model compound of the small-molecule Bcl-2 inhibitor (BH3I-2) and characterized by 1H NMR and IR measurements. The structures of BCNCPB–OH and its deprotonated form (BCNCPB–O–NEt4) were determined by X-ray analysis. BCNCPB–OH has an intramolecular OH···O=C hydrogen bond and BCNCPB–O–NEt4 has an intramolecular NH···O(oxyanion) hydrogen bond in the solid and solution states. The solution structures of protonated and deprotonated BH3I-2′ (BH3I-2 analogue) were determined by 1H NMR, NOESY, and IR measurements. They have similar conformations to those of the corresponding model compounds. A pKa value of BCNCPB–OH of 5.1 is considered a very low value for phenol derivatives, suggesting the possibility that BH3I-2 binds to protein in the deprotonated form having an intramolecular NH···O(oxyanion) hydrogen bond.
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