Abstract A series of diaminobenzo [f]-and diaminobenzo [h] pyrimido [4, 5-b] quinolines 1–11 were designed as 5-deaza tetracyclic nonclassical, lipophilic antifolates. The compounds were designed as conformationally semi-rigid and rigid analogs of 2, 4-diamino-6-phenyl-12 and 2, 4-diamino-7-phenylpyrido [2, 3-d] pyrimidines 13 and 14. The target compounds were synthesized by cyclocondensation of chlorovinyl aldehydes obtained from appropriately ...