Synthesis of butanoic acid 4,4′-[(4E, 6Z, 9Z-pentadecatrien-2-ynylidene)-bis with leukotriene- like activity: Novel acetylenic acetals and dithioacetals as antagonists of leukotriene-C4
✍ Scribed by Anil K. Saksena; Michael J. Green; Pietro Mangiaracina; Jesse K. Wong; William Kreutner; Arax R. Gulbenkian
- Book ID
- 104229170
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 247 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A selective exchange reaction of the symmetrical acetal 3 with protected cysteine readily provided the hemi-thioacetals 9,a and lla related to leukotrlene-E . Use of acetylene- bis-(diethyl acetal) 12 led to a facile synth&is of the title compound 1 4 a. Its corresponding hexahydt? analogs displayed marked antagonist activity agznst LT-C4 induced contractions on isolated guinea pig lung parenchyma. Leukotrienes C4, D4 and E4, now considered to be the main constituents of SRS-A, may be prime mediators of allergic diseases such as asthma and allergic rhinitis etc.' Complete details will be given in the full paper, manuscript in preparation; in-vitro -~ data refer to lo-8M LT-C4 induced contractions on the isolated guinea pig lung parenchyma P. Sheard, M.C. Holroyd, A.M. Ghelani, *J.R. Bantik, and T.B. Lee, Leukotrienes and other Lipoxygenase Products, 229, Raven Press (1982). Satisfactory IR, PMR, CMR, and MS (EI and FAR) were obtained for all new compounds. After this manuscript was completed, two aromatic dithioacetals as selective antayonists of LT-D4 were reported, see: C.D. Perchonock et. al., 189th ACS National Meeting (Abstract No. 85, Div. Med. Chem.), Miami Reach, Flori,da (1985).