Biological activity of alkyl 2-(acylthio)benzoates.
Of a series of synthetic alkyl 2-(acylthio)benzoate (1-20), all the derivatives except for n-butyl 2-butyrylthiobenzoate (18) and n-butyl 2-n-valerylthiobenzoate (20) showed clear phytogrowth-inhibitory activity. All the compounds tested except for methyl 2-butyrylthiobenzoate (3) exhibited cytotoxic activity on mouse splenic T cells. Strong phytogrowth-inhibition and cytotoxic activity were found with 1, 6, 11 and 16 with an acetylthio group at C-2, suggesting that the acetyl group seems to play an important role in both activities of alkyl 2-(acylthio)benzoates. Among them, methyl 2-acetylthiobenzoate (1) was the strongest inhibitor. On the other hand, potent inhibition of prolyl endopeptidase was exhibited by 2, 7, 12 and 17 with a propionylthio group at C-2. These findings imply that a propionyl group might be useful for increasing the inhibitory activity against on prolyl endopeptidase.
Matsumura
E
E
Osaka University of Pharmaceutical Sciences, Japan.
Nishinaka
T
T
Tsujibo
H
H
Hachiken
H
H
Miki
Y
Y
Sakagami
Y
Y
Inamori
Y
Y
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001565:Benzoates / Q000138:chemical synthesis* / Q000494:pharmacology; D001937:Brassica / Q000187:drug effects / Q000254:growth & development; D010450:Endopeptidases / Q000378:metabolism; D007166:Immunosuppressive Agents / Q000494:pharmacology; D051379:Mice; D008807:Mice, Inbred BALB C; D008810:Mice, Inbred C57BL; D011480:Protease Inhibitors / Q000494:pharmacology; D013154:Spleen / Q000166:cytology / Q000187:drug effects / Q000201:enzymology; D013329:Structure-Activity Relationship; D013601:T-Lymphocytes / Q000187:drug effects / Q000201:enzymology / Q000276:immunology
D000970:Antineoplastic Agents; D001565:Benzoates; D007166:Immunosuppressive Agents; D011480:Protease Inhibitors; D010450:Endopeptidases