Oxidative metabolism of N-isopropyl-α-(2-methylhydrazino)-p-toluamide hydrochloride (procarbazine) by rat liver microsomes was written by Dunn, Danny L.;Lubet, Ronald A.;Prough, Russell A.. And the article was included in Cancer Research in 1979.Electric Literature of C11H13NO2 This article mentions the following:
The oxidative metabolism of procarbazine-HCl (I) [366-70-1] by rat liver microsomes was studied by 3 different biochem. assays. The major, stable microsomal metabolite produced was the azo derivative, N-isopropyl-α-(2-methylazo)-p-toluamide [2235-59-8], which can undergo a rapid chem. conversion to an aldehyde, p-formyl-N-isopropylbenzamide [13255-50-0], and methylhydrazine upon the addition of acid. The rate of metabolism could most conveniently be determined spectrophotometrically by reacting the resultant methylhydrazine with p-dimethylaminobenzaldehyde. Rates of metabolism ranged from 13.4 to 14.1 nmol/min/mg of microsomal protein. Inhibitor and induction studies indicated that the cytochrome P-450-dependent monooxygenase [9038-14-6] system is responsible for this oxidation reaction. Several possible mechanisms were considered. The azo derivative of I was further oxidized to 2 isomeric azoxy derivatives, N-isopropyl-α-(2-methyl-NNO-azoxy)-p-toluamide [66944-55-6] and N-isopropyl-α-(2-methyl-ONN-azoxy)-p-toluamide [66944-56-7], at a metabolic rate 10-15% as large as the rate of I oxidation In addition, the affinity of the azo derivative for the monooxygenase was high relative to that of the parent hydrazine. The reaction was inhibited by cytochrome P-450 inhibitors and was sensitive to the in vitro addition of several thiono-S-containing compounds The azoxy compounds were also metabolized by microsomal fractions from liver and yielded p-formyl-N-isopropylbenzamide as a product. This complex in vitro metabolic scheme is analogous to the in vivo metabolism of 1,2-dimethylhydrazine and suggests that I may be metabolically activated to yield alkylating agents capable of expressing carcinogenic and/or toxic effects by a mechanism common for at least these 2 N,N‘-disubstituted hydrazines. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Electric Literature of C11H13NO2).
4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Electric Literature of C11H13NO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics