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Boronic Acid-Containing Aminopyridine- And Aminopyrimidinecarboxamide CXCR1/2 Antagonists: Optimization of Aqueous Solubility and Oral Bioavailability

Boronic Acid-Containing Aminopyridine- And Aminopyrimidinecarboxamide CXCR1/2 Antagonists: Optimization of Aqueous Solubility and Oral Bioavailability

Aaron D Schuler, Courtney A Engles, Dean Y Maeda, Mark T Quinn, Liliya N Kirpotina, Winston N Wicomb, S Nicholas Mason, Richard L Auten, John A Zebala

Bioorg Med Chem Lett. 2015 Sep 15;25(18):3793-7.

PMID: 26248802

Abstract:

The chemokine receptors CXCR1 and CXCR2 are important pharmaceutical targets due to their key roles in inflammatory diseases and cancer progression. We have previously identified 2-[5-(4-fluoro-phenylcarbamoyl)-pyridin-2-ylsulfanylmethyl]-phenylboronic acid (SX-517) and 6-(2-boronic acid-5-trifluoromethoxy-benzylsulfanyl)-N-(4-fluoro-phenyl)-nicotinamide (SX-576) as potent non-competitive boronic acid-containing CXCR1/2 antagonists. Herein we report the synthesis and evaluation of aminopyridine and aminopyrimidine analogs of SX-517 and SX-576, identifying (2-{(benzyl)[(5-boronic acid-2-pyridyl)methyl]amino}-5-pyrimidinyl)(4-fluorophenylamino)formaldehyde as a potent chemokine antagonist with improved aqueous solubility and oral bioavailability.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP139301272	4-(Trifluoromethoxy)phenylboronic acid	139301-27-2	Price
AP175676650	2-(Trifluoromethoxy)phenylboronic acid	175676-65-0	Price
AP475102126	(N-Boc-5-chloro-2-indolyl)boronic acid	475102-12-6	Price

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