Studies on the derivatives of aziridine. I. synthesis and immunopharmacological analysis of amides of alpha-aziridinyl- beta-/p-chlorobenzoyl/-propionic acid.
Several new aziridinyl derivatives of beta-/p-chlorobenzoyl/propionic acid were synthesized (3, 5, 7, 14-18). The gamma-/p-chlorophenyl/-dihydrofuran-2-one 2 and beta-/p-chlorobenzoyl/acrylic acid 4 were used as the substrates. Compound 2 reacts with ethylenimine yielding aziridinylamide of beta-/p-chlorobenzoyl/-propionic acid 3. The sodium salt of acid 4 and methyl ester 6 were converted by reactions with ethylenimine into appropriate alpha-aziridinyl derivatives 5 and 7. The acid 4 in the reaction with phosphorus pentachloride gives the acid chloride 8 which is transformed under the influence of appropriate amines into corresponding amides 9-13. These amides react with ethylenimine giving the appropriate alpha-aziridinyl derivatives of beta-/p-chlorobenzoyl/-propionic acid 14-18. Pharmacological analysis revealed that the compounds studied possessed immunotropic activity; they modulate both humoral as well as cellular immune response. Their effect has been shown to be related to chemical structure and to substituents of the carboxyl group in particular.
D000179:Acrylates / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D000276:Adjuvants, Immunologic / Q000138:chemical synthesis*; D000818:Animals; D000917:Antibody Formation / Q000187:drug effects; D001388:Aziridines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D001389:Azirines / Q000138:chemical synthesis*; D002723:Chlorobenzoates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D006087:Graft vs Host Reaction; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008815:Mice, Inbred Strains; D011422:Propionates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D012397:Rosette Formation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013601:T-Lymphocytes / Q000187:drug effects / Q000276:immunology
D000179:Acrylates; D000276:Adjuvants, Immunologic; D001388:Aziridines; D001389:Azirines; D002723:Chlorobenzoates; D007202:Indicators and Reagents; D011422:Propionates