Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)- dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

Tadashi Honda; Albena T. Dinkova-Kostova; Emilie David; Eric M. Padegimas; Chitra Sundararajan; Melean Visnick; Ron Bumeister; W. Christian Wigley

doi:10.1016/j.bmcl.2011.03.018

Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)- dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

Tadashi Honda, Albena T. Dinkova-Kostova, Emilie David, Eric M. Padegimas, Chitra Sundararajan, Melean Visnick, Ron Bumeister, W. Christian Wigley

School of Medicine

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic)imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted.

Original language	English (US)
Pages (from-to)	2188-2191
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2011.03.018
State	Published - Apr 15 2011

Keywords

Acetylenicimidazole
Inducers of heme oxygenase-1 and
Inhibitors of nitric oxide production
NQO1
Oleanolic acid
Triterpene

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

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10.1016/j.bmcl.2011.03.018

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Honda, T., Dinkova-Kostova, A. T., David, E., Padegimas, E. M., Sundararajan, C., Visnick, M., Bumeister, R., & Christian Wigley, W. (2011). Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)- dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent. Bioorganic and Medicinal Chemistry Letters, 21(8), 2188-2191. https://doi.org/10.1016/j.bmcl.2011.03.018

Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)- dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent. / Honda, Tadashi; Dinkova-Kostova, Albena T.; David, Emilie et al.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 8, 15.04.2011, p. 2188-2191.

Research output: Contribution to journal › Article › peer-review

Honda, T, Dinkova-Kostova, AT, David, E, Padegimas, EM, Sundararajan, C, Visnick, M, Bumeister, R & Christian Wigley, W 2011, 'Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)- dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent', Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 8, pp. 2188-2191. https://doi.org/10.1016/j.bmcl.2011.03.018

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abstract = "To explore more potent N-acylimidazole analogues of CDDO than CDDO-Im, which is one of the most potent compounds in several widely used bioassays related to protection against inflammation and carcinogenesis; we have synthesized and evaluated five new N-acyl(acetylenic)imidazole analogues. Among them, 4-ethynylimidazole 4 is nearly equivalent to CDDO-Im in potency in these bioassays. Remarkably, the solid form of 4 is more stable than that of CDDO-Im. These findings suggest that 4 is a very promising anti-inflammatory and cytoprotective agent and its further preclinical evaluation is warranted.",

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Synthesis and biological evaluation of 1-[2-cyano-3,12-dioxooleana-1,9(11)- dien-28-oyl]-4-ethynylimidazole. A novel and highly potent anti-inflammatory and cytoprotective agent

Abstract

Keywords

ASJC Scopus subject areas

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