Substituted indoles as potent and orally active 5-lipoxygenase activating protein (FLAP) inhibitors.
Publication
, Journal Article
Frenette, R; Hutchinson, JH; Léger, S; Thérien, M; Brideau, C; Chan, CC; Charleson, S; Ethier, D; Guay, J; Jones, TR; McAuliffe, M; Tagari, P ...
Published in: Bioorganic & medicinal chemistry letters
August 1999
This paper reports on the SAR investigation of inhibitors of 5-lipoxygenase activating protein (FLAP) based on MK-0591. Emphasis was made on modifications to the nature of the link between the indole and the quinoline moieties, to the substitution pattern around the two heterocycles and to possible replacements of the quinoline moiety. Lead optimization culminated in (3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(pyridin-2-ylmethoxy)-ind ol-2-yl]-2,2-dimethylpropanoic acid (18k), as a potent inhibitor of leukotriene biosynthesis that is well absorbed and active in functional models.
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Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
August 1999
Volume
9
Issue
16
Start / End Page
2391 / 2396
Related Subject Headings
- Structure-Activity Relationship
- Rats
- Quinolines
- Membrane Proteins
- Medicinal & Biomolecular Chemistry
- Lipoxygenase Inhibitors
- Indoles
- In Vitro Techniques
- Humans
- Dogs
Citation
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Frenette, R., Hutchinson, J. H., Léger, S., Thérien, M., Brideau, C., Chan, C. C., … Girard, Y. (1999). Substituted indoles as potent and orally active 5-lipoxygenase activating protein (FLAP) inhibitors. Bioorganic & Medicinal Chemistry Letters, 9(16), 2391–2396. https://doi.org/10.1016/s0960-894x(99)00399-6
Frenette, R., J. H. Hutchinson, S. Léger, M. Thérien, C. Brideau, C. C. Chan, S. Charleson, et al. “Substituted indoles as potent and orally active 5-lipoxygenase activating protein (FLAP) inhibitors.” Bioorganic & Medicinal Chemistry Letters 9, no. 16 (August 1999): 2391–96. https://doi.org/10.1016/s0960-894x(99)00399-6.
Frenette R, Hutchinson JH, Léger S, Thérien M, Brideau C, Chan CC, et al. Substituted indoles as potent and orally active 5-lipoxygenase activating protein (FLAP) inhibitors. Bioorganic & medicinal chemistry letters. 1999 Aug;9(16):2391–6.
Frenette, R., et al. “Substituted indoles as potent and orally active 5-lipoxygenase activating protein (FLAP) inhibitors.” Bioorganic & Medicinal Chemistry Letters, vol. 9, no. 16, Aug. 1999, pp. 2391–96. Epmc, doi:10.1016/s0960-894x(99)00399-6.
Frenette R, Hutchinson JH, Léger S, Thérien M, Brideau C, Chan CC, Charleson S, Ethier D, Guay J, Jones TR, McAuliffe M, Piechuta H, Riendeau D, Tagari P, Girard Y. Substituted indoles as potent and orally active 5-lipoxygenase activating protein (FLAP) inhibitors. Bioorganic & medicinal chemistry letters. 1999 Aug;9(16):2391–2396.
Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
August 1999
Volume
9
Issue
16
Start / End Page
2391 / 2396
Related Subject Headings
- Structure-Activity Relationship
- Rats
- Quinolines
- Membrane Proteins
- Medicinal & Biomolecular Chemistry
- Lipoxygenase Inhibitors
- Indoles
- In Vitro Techniques
- Humans
- Dogs