Synthesis of beta-hydroxy-propenamide derivatives and the inhibition of human dihydroorotate dehydrogenase

Taek Hyeon Kim; Hye-Sun Na; Monika Löffler

doi:10.1007/BF02976829

Synthesis of beta-hydroxy-propenamide derivatives and the inhibition of human dihydroorotate dehydrogenase

Arch Pharm Res. 2003 Mar;26(3):197-201. doi: 10.1007/BF02976829.

Authors

Taek Hyeon Kim¹, Hye-Sun Na, Monika Löffler

Affiliation

¹ Department of Applied Chemistry, College of Engineering, Chonnam National University, Gwangju 500-757, Korea. thkim@chonnam.ac.kr

PMID: 12723931
DOI: 10.1007/BF02976829

Abstract

Novel beta-hydroxy propenamides as analogues of the active metabolite of leflunomide (A 771726) were synthesized and evaluated for their inhibitory activity on dihydroorotate dehydrogenase (DHODH) in an investigation into their immunosuppressive activity. Compounds 2a, 3a, and 3h were approximately 4-40 times more potent than leflunomide in their activity while they were-less active than A 771726.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aniline Compounds / chemical synthesis*
Aniline Compounds / chemistry
Aniline Compounds / pharmacology
Crotonates
Dihydroorotate Dehydrogenase
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Humans
Hydroxybutyrates / chemical synthesis*
Hydroxybutyrates / chemistry
Hydroxybutyrates / pharmacology
Isoxazoles / metabolism
Leflunomide
Nitriles
Oxidoreductases Acting on CH-CH Group Donors / antagonists & inhibitors*
Oxidoreductases Acting on CH-CH Group Donors / metabolism
Toluidines

Substances

Aniline Compounds
Crotonates
Dihydroorotate Dehydrogenase
Enzyme Inhibitors
Hydroxybutyrates
Isoxazoles
Nitriles
Toluidines
teriflunomide
Oxidoreductases Acting on CH-CH Group Donors
Leflunomide