Alkylating nitrogen mustards

Name Structure
Chloambucil chloambucil
Cyclophosphamide cyclophosphamide
Ifosfamide ifosfamide


  1. Compare alkylating ability of mustine shown below to the more recently developed nitrogen mustards from the table above.


  1. Suggest a method to prepare HN3 shown below.


  1. Use resonance to rationalize which position of guanine would be preferentially alkylated by these agents.
  2. Would you expect nitrogen mustards to cross link bases from the same DNA strand or from different strands? How does this compare to the action of cis-platin?