4-(4-Acetylphenylamino)cycloocteno [4,5]thieno [2,3-d]pyrimidine (4) was prepared and condensed with certain aldehydes, phenylhydrazine, malononitrile to obtain 5a-d, 6 and 7, respectively. 4-Hydrazino & 4-substituted amino derivatives of 2-arylcycloocteno[4,5]thienopyrimidines 10a-c & 11a-i were synthesized. Cyclization of the hydrazino compounds 10a-c with orthoalkanoate esters or the arylidene derivatives 12a-c with bromine in acetic acid afforded the fused triazolo system 13a-i. Reaction of the hydrazino compound 10c with acetic anhydride gave 15 while the reaction of 10b,c with acid chlorides gave 16a-d. Furthermore, the tetrazolothienopyrimidines 17a-c were synthesized. Some of the newly synthesized compounds were tested for their antimicrobial activity.

Several triazenoindazoles 3a-e and triazinopyrazolopyridines 6a-i were prepared through the reaction of the corresponding 3-amino-4-chloroindazole and 3-aminopyrazolopyridine diazonium salts 2 and 5 with a number of secondary amines. All compounds were evaluated for their in vitro cytotoxic activity on three cell lines, HepG2, MCF7, and HeLa. Most compounds inhibited cell growth with IC(50) less than 0.1 microM. Compound 6d was the most potent, with an IC(50) of 0.03 microM against HepG2 and 0.05 microM against MCF7 and HeLa cells.