Studies on the Syntheses of Sulfur Containing Pyrimido[5, 4-d]pyrimidine Derivatives. I. Syntheses of Pyrimido[5, 4-d]pyrimidine Derivatives Possessing Methylsulfonyl or Sulfonamide Group at 2-Position
Open Access
- 1 January 1976
- journal article
- research article
- Published by Pharmaceutical Society of Japan in YAKUGAKU ZASSHI
- Vol. 96 (5) , 578-585
- https://doi.org/10.1248/yakushi1947.96.5_578
Abstract
Thirty-one kinds of pyrimido[5,4-d]pyrimidine derivatives possessing methylsulfonyl or sulfonamide group at 2-position were prepared by the reaction of 4,8-disubstituted 6-chloro-2-methylsulfonylpyrimido[5,4-d]pyrimidine or 4,8-disubstituted 6-chloropyrimido[5,4-d]pyrimidine-2-sulfonyl chloride and various amines. Reaction of N,N-bis(2-hydroxyethyl)-6-chloro-4,8-dipiperidinopyrimido[5,4-d]pyrimidine-2-sulfonamide with an excess of diethanolamine by heating gave dipyridamole with elimination of the SO2 group. The N-(2-hydroxyethyl)-N-methyl-sulfonamide derivative also underwent a similar elimination of the SO2 group. The relationship between the structure of these derivatives and their activity as coronary vasodilators and inhibitor of platelet aggregation was examined [in dogs]. 6-Bis(2-hydroxyethyl)amino-2-methylsulfonyl-4,8-dipiperidinopyrimido[5,4-d]pyrimidine exhibited a strong coronary vasodilation, and some sulfonamide derivatives exhibited a comparatively strong inhibition of platelet aggregation.This publication has 0 references indexed in Scilit: