70590-43-1Relevant articles and documents
Synthesis of the thiazolone analogue of the acetylcholinesterase inhibitor, huperzine A
Kozikowski,Tuckmantel,Saxena,Doctor
, p. 1256 - 1266 (1994)
The preparation of an analogue 3a of the acetylcholinesterase inhibitor, huperzine A (1), is described in which the pyridinone moiety of the natural product is replaced with a thiazolone moiety. The synthesis started from cyclohexane-1,4-dione monoethylene ketal (7) by first annulating the thiazole ring using the Gewald protocol (→8) and then constructing the bicyclo[3.3.1]nonane substructure using our previously described Michael addition/aldol condensation methodology. The central problem was the protection of the thiazolone carbonyl group; only the 2-unsubstituted thiazole survived the reaction conditions of the first half of the synthesis. Refunctionalization was later effected by lithiation and subsequent chlorination with hexachloroethane (30→31). Compound 3a was ineffective in the acetylcholinesterase inhibition assay in concentrations up to 14 μM.
New benzo [d] thiazole derivatives, process for their preparation and their therapeutic applications
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, (2008/06/13)
This invention relates to compounds having the general formula: STR1 and their pharmaceutically acceptable acid addition salts having the formula: STR2 in which: R represents hydrogen or a C1-4 alkyl radical, R' represents hydrogen or a C1-4 alkyl radical, m is 0, 1, 2 or 3, n is 3, 2, 1 or 0, the sum m+n being always equal to 3, and X- represents an anion formed by a pharmaceutically acceptable acid. Said compounds are typically useful as analgesic agents and as stimulants of the sympathetic nervous system, and also as central and peripheral vasoregulator agents.