O

distribution before alkylation takes place, and therefore allows oral administration. The simplest aromatic nitrogen mustard is compound 5.12, which has the disadvantage of not being water soluble. Addition of a carboxyl group led to the soluble analog 5.13, which was inactive. However, simple separation of the carbox-ylic group from the aromatic ring by a spacer yielded active compounds such as chlorambucil, which contains a butyric acid side chain. This compound is used to treat chronic lymphocytic leukemia and lymphomas. Bendamustin is a related nitrogen mustard where the benzene ring has been replaced by a benzimidazole.

HO2C

HO2C

Bendamustin

R = (CH2)3CO2H Chlorambucil

Bendamustin

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