Synthesis of functionalized cinnamaldehyde derivatives by an oxidative Heck reaction and their use as starting materials for preparation of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase inhibitors.

ABSTRACT: Cinnamaldehyde derivatives were synthesized in good to excellent yields in one step by a mild and selective, base-free palladium(II)-catalyzed oxidative Heck reaction starting from acrolein and various arylboronic acids. Prepared ?,?-unsaturated aldehydes were used for synthesis of novel ?-aryl substituted fosmidomycin analogues, which were evaluated for their inhibition of Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase. IC(50) values between 0.8 and 27.3 ?M were measured. The best compound showed activity comparable to that of the most potent previously reported ?-aryl substituted fosmidomycin-class inhibitor.

SUBMITTER: Nordqvist A 

PROVIDER: S-EPMC3203620 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature