Synthesis and biological evaluation of amino acid methyl ester conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid against the production of nitric oxide (NO)
Onyango, Evans; Liangfeng, Fu; Cao, Martineet al.
2014 • In Bioorganic and Medicinal Chemistry Letters
[en] 2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO, 2) was condensed with various amino acid methyl esters at the C-28 carboxylic acid. The new amide conjugates were evaluated for their inhibition of nitric oxide (NO) production in RAW264.7 cells stimulated with interferon-γ (IFNγ). Of these new compounds, CDDO conjugates with alanine, valine, and serine are nearly equipotent to CDDO-ethyl amide (4), a triterpenoid with promising biological activity in numerous disease models. Some of these conjugates also induce the in vitro expression of heme oxygenase-1, and inhibit the proliferation of Panc-1343 pancreatic cells.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Onyango, Evans; Dartmouth College > Chemistry
Liangfeng, Fu; Dartmouth College > Chemistry
Cao, Martine ; Dartmouth Medical School > Pharmacology and Toxicology
Liby, Karen; Dartmouth Medical School > Pharmacology and Toxicology
Sporn, Michael; Dartmouth Medical School > Pharmacology and Toxicology
Gribble, Gordon; Dartmouth College > Chemistry
Language :
English
Title :
Synthesis and biological evaluation of amino acid methyl ester conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid against the production of nitric oxide (NO)
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