Synthesis and antibacterial activity of 5-adamantan-1-yl-methyl analogues of trimethoprim.

A series of new trimethoprim [5-(3,4,5-trimethoxy-benzyl)-pyrimidine-2,4- diamine] analogues were prepared by condensation of adamantane-1-carbaldehyde with 3-methoxypropionitrile, followed by reaction of resulting mixture of 2-adamantan-1-ylmethyl-3-methoxy-acrylonitrile and 3-adamantan-1-yl-2-methoxymethyl-acrylonitrile with guanidine, acetamidine and thiourea, respectively. The activity of compounds obtained and sulfamethoxazole, alone and in combination, against several bacterial strains, as well as fungi was investigated.