Synthesis of Angiotensin Converting Enzyme Inhibitors

안지오텐신 변환효소(變換酵素) 억제(抑制) 작용(作用) 물질(物質)의 합성(合成)

Phenylurea, phenylthiourea, benzylcarbamate and toluenesulfonate of L-alanyl-L-proline(comp. $3{\sim}6$) were synthesized and their effects against angiotensin-converting enzyme (ACE) were tested. Comp. 3 showed only mild inhibitory activities against ACE while comp. $4{\sim}6$ were inert indicating that those functional groups were not suitable for interactions with ACE. Ortho-hydroxy- or ortho-carboxy-benzamide of proline (comp. 7) and phenylalanine (comp. 8 and 9) were also tested. Of the benzamides, ortho-hydroxy function was unsuitable to exert inhibitory activities against ACE. Ortho-carboxy group of 9 seemed to have mild interactions with active site of ACE possibly because of the shorter distance between the amide and ortho-carboxyl group of the compound than the corresponding two active sites of the enzyme.