Nitrogen mustard analogues

The nitrogen mustard analogues are nitrogen derivatives of sulfur mustard, used as poison gas in World War I. Agents include cyclophosphamide, mechlorethamine, chlorambucil, melphalan, ifos-famide, uramustine and estramustine. 

The above evidence should not be interpreted as meaning that hydrolytic dehalogenation can never be demonstrated unambiguously. Indeed, the next subsection will document reactions of multiple dehalogenation that are only consistent with a hydrolytic mechanism. But before doing so, we examine here the hydrolysis of medicinal nitrogen mustards and of their sulfur analogue, the infamous sulfur mustard. 

The management of cancer includes treatment with alkylating agents (nitrogen mustards and alkyl sulfonates), antimetabolites (methotrexate and purine analogues), natural products (vinca alkaloids and taxol), miscellaneous compounds (hydroxyurea, procarbazine, and m-platinum), hormones (estrogens and corticosteroids), and radioactive isotopes. 

Fleer R, Brendel M. 1982. Toxicity, interstrand cross-links and DNA fragmentation induced by activated cyclophosphamide in yeast Comparative studies on 4-hydroxyperoxy-cyclophosphamide, its monofunctional analogue, acrolein, phosphoramide mustard, and nor-nitrogen mustard. Chem Biol Interact 39 1-15. 

Platinum analogues Nitrogen mustards Nitrosoureas Other... 

A number of synthetic analogues of distamycin and netropsin have been found to have excellent antitumor activity. For example, FCE 24517 (41), which is a nitrogen mustard-distamycin hybrid, is in clinical trials . The distamycin derivative (42) has increased water solubihty and enhanced cellular uptake <95H(4l)337>, and (43) is one of several related antitumor compounds with... 

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