Cytotoxic compounds. Part XVII. o-, m-, and p-(Bis-2-chloroethylamino)phenol, p-[N-(2-chloroethyl)methylamino]phenol, NN-bis-2-chloroethyl-p-phenylenediamine, and NN-bis-2-chloroethyl-N′-methyl-p-phenylenediamine as sources of biologically active carbamates

Abstract

New or improved syntheses are reported of the nitrogen mustards named in the title, and of methyl m-(bis-2-chloroethylamino)-p-hydroxybenzoate. By reactions of the amines with aryl chloroformates, or of the phenols with aryl isocyanates or with isocyanates derived from α-amino-esters, carbamates containing alkyl, chloro-, alkoxy-, hydroxy-, methoxycarbonyl, carboxy-, acetyl, and sulphamoyl groups are obtained. Some of these have shown marked anti-tumour activity. p-(Bis-2-chloroethylamino)phenyl chloroformate has been prepared; it provides an alternative route to mustard carbamates. Some carbamates of the lachrymator type have been synthesised from p-aminophenacyl chloride.