Substituted nitrogen bridgehead heterocycles of potential smooth muscle relaxant and antihypertensive activities

Pyrrolo [1,2-c] pyrimidine derivatives I reacted with various acid chlorides to afford a number of 3-substituted pyrimido [5,4-e] pyrrolo [1,2-c] pyrimidines. The 3-chlorocarbonyl intermediate I-A reacted with different alcohols to give the corresponding esters. Moreover, 3-chloromethyl derivative I-B reacted with thiourea, alkoxides and sodium salts of aromatic acids to yield thiouronium salts, ethers and esters, respectively. Some members were tested as smooth muscle relaxant diuretic and hypotensive activities. It was shown that compound VII-a is the potent as hypotensive and diuretic agent. Also, it was noticed that, while all the test substances inhibit the uterine motility, VII-a stimulates the uterine motility in all stages