Cyanoguanidine bioisosteres in potassium channel openers: Evaluation of 3,4-disubstituted-1,2,5-thiadiazole-1-oxides
β Scribed by Heinrich J. Schostarez; Theresa J. O'Sullivan; Vincent E. Groppi; Loretta A. Cipkus-Dubray
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 252 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0960-894X
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β¦ Synopsis
Bioisostefic substitution of the cyanoguanidine group found in pinacidil (1) with a 3,4-diamino-l,2,5thiadiazole-l-oxide moiety and replacement of the 4-aminopyridine group with a 3,5-dichlorophenyl group has resulted in a new structural class of potassium channel opener (PCO).
π SIMILAR VOLUMES
3,4-Diphenyl-1,2,5-thiadiazole 1-oxide (1a) in acetonitrile solution is electroreduced to 2,4,6-triphenyl-1,3,5triazine and 3,4-diphenyl-1,2,5-thiadiazole. This behavior is very different from that of similar compounds with other oxidation states of the heterocyclic sulfur atom, such as the 1,1-diox
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1.4-Dlalkyl-and 1,4-diar~I-~,3-bls(hydr(~~~lmlno)butancs 7, 1rom reductton ol the corresponding 1,4-dlsubsututed 23.dmltrw I ,3-butadlenes 2, are transformed M Ith satlsl'actor> ytelds Into 3,4disubstituted 1,?,5-oxadt~~~le-2-o-rlde 5 and 4,S-disubstttuted ?-phen~l-2H-1,2.3-triazole-l-ou~des 6. Dtmt