Synthesis and pharmacological profile of two novel heterocyclic chromanols, CP-80,798 and CP-85,958, as potent LTD4 receptor antagonists

Andrews, ED; Antognoli, G.W.; Breslow, R; Carta, M. P.; Carty, Thomas J.; Chambers, Robert; Cheng, John B.; Cohan, V. L.; Collins, J.L.; Damon, David B.; Delehunt, J. C.; Eggler, James F.; Eskra, James D.; Freiert, K. W.; Hada, William A.; Marfat, Anthony; Masamune, Hiroko; Melvin, Lawrence S.; Mularski, Christian J.; Naclerio, B.A.; Pazoles, Christopher J.; Pillar, J.; Rappach, L.A.; Reiche, P.; Rusek, Frank W.; Sherman, H. C.; Shirley, J.T.; Sweeney, Francis J.; Tickner, Jeanene E.; Watson, J. W.; Wright, Charles F.

doi:10.1016/0960-894x(95)00225-i

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2024

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Cited by 11 publications

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“…CP-199.330, CP-199.331, and CP-85.958, featuring a syn -chromanol backbone, are under clinical trials as selective leukotriene D4 (LTD4) antagonists for treating asthma (Figure ). The typical transition-metal-free routes to chroman-4-ol/ones involve the NHC-catalyzed ‘Stetter’ reaction and radical-mediated cyclization of O -allyl salicylaldehydes . However, these methods often suffer from poor diastereoselectivity.…”

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confidence: 99%

Ni-Catalyzed Diastereoconvergent Intramolecular Alkene–Aldehyde Reductive Coupling: A Route to syn-Chromanols

Ghosh,

Rooj,

Chakrabortty

et al. 2024

Org. Lett.

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We demonstrate for the first time a nickel-catalyzed diastereoconvergent reductive coupling of a heteroatom-attached allyl moiety with aldehydes, viz., O-allyl, O-cinnamyl salicylaldehydes, and others, to afford syn-chromanols exclusively. The reaction proceeds through a [2 + 2 + 1] oxidative cycloaddition involving the active catalyst. This method is applicable to both terminal and internal olefin substrates. The formal syntheses of have been demonstrated. Control experiments, mass spectrometric analysis, and DFT studies supported the plausible mechanism and the origin of exclusive synselectivity.

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confidence: 99%