Synthesis of methyl (1R,2S)-2-[(1′Z,4′Z,7′Z)-hexadeca-1′,4′,7′-trienyl]cyclopropanecarboxylate: a potential inhibitor of the enzyme 5-lipoxygenase
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1503-1508
- https://doi.org/10.1039/p19940001503
Abstract
We describe the synthesis of a novel cyclopropyl analogue of arachidonic acid via a convergent synthesis that employed methyl (1R,2S)-2-formylcyclopropanecarboxylate in conjunction with the ylide from (3Z,6Z)-pentadeca-3,6-dienyl(triphenyl)phosphonium iodide. This compound was designed to inhibit the enzyme 5-lipoxygenase after reaction to form a putative α-cyclopropylmethylene radical.Keywords
This publication has 8 references indexed in Scilit:
- 5-Lipoxygenase: properties, pharmacology, and the quinolinyl(bridged)aryl class of inhibitorsJournal of Medicinal Chemistry, 1992
- Synthesis of 2′,3′-dideoxy-2′,3′-α-methanocytidineCarbohydrate Research, 1990
- Biosynthesis, catabolism, and biological properties of HPETEs, hydroperoxide derivatives of arachidonic acidFree Radical Biology & Medicine, 1989
- Evidence in favor of an organoiron-mediated pathway for lipoxygenation of fatty acids by soybean lipoxygenaseJournal of the American Chemical Society, 1987
- Ethanoarachidonic acids. A new class of arachidonic acid cascade modulators. 1. Monoethano compoundsThe Journal of Organic Chemistry, 1983
- Synthesis of three potential inhibitors of leukotriene biosynthesisJournal of Medicinal Chemistry, 1983
- Synthesis and 5-lipoxygenase inhibitory activities of eicosanoid compoundsJournal of Medicinal Chemistry, 1983
- Novel reagent system for converting a hydroxy-group into an iodo-group in carbohydrates with inversion of configuration. Part 2Journal of the Chemical Society, Perkin Transactions 1, 1980