Nitrogen and sulfur analogues of the secoCI alkylating agent: Synthesis and cytotoxicity

The first synthesis of seco-Cl alkylating agents bearing a nitrogen or sulfur substituent in place of the oxygen at C-6 is described. In comparison with a phenol, an amino substituent confers reduced but significant cytotoxicity, even when mono- or dimethylated, while sulfur analogues are considerably less potent.