Synthesis of N-arylsulfonyl DL-phenylserine derivatives exhibiting anti-inflammatory activity in experimental studies.
Synthesis and evaluation of anti-inflammatory activity in rats with adjuvant arthritis of aryl sulfonyl derivatives of nonproteinogenic aromatic amino acids is reported. The studied compounds were synthesized by introducing residues of benzene-, p-toluene-, and p-bromobenzene sulfonic acids into threo-DL-phenylserine and erythro-DL-p-nitrophenylserine structures. From the set of 12 compounds tested in animal screening, N-(p-bromobenzenesulfonyl)-erythro-DL-p-nitrophenylserine ethyl ester 12 demonstrated the most pronounced anti-inflammatory activity. This compound inhibited inflammation process in polyarthritis phase by 53% (P < 0.001) though it was slightly toxic (LD50 > 6,000 mg kg(-1) for mice).
Straukas
Juozapas
J
Institute of biochemistry, Vilnius, Lithuania.
Dirvianskyte
Nijole
N
Astrauskas
Vytautas
V
Butkus
Eugenius
E
D000276:Adjuvants, Immunologic / Q000009:adverse effects; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology*; D001169:Arthritis, Experimental / Q000188:drug therapy* / Q000276:immunology / Q000473:pathology; D001190:Arylsulfonates / Q000737:chemistry* / Q000494:pharmacology*; D001554:Benzene / Q000737:chemistry; D006614:Hindlimb / Q000187:drug effects / Q000473:pathology; D007274:Injections, Intraperitoneal; D007596:Joints / Q000187:drug effects / Q000473:pathology; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D008807:Mice, Inbred BALB C; D051381:Rats; D017208:Rats, Wistar; D012694:Serine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000276:Adjuvants, Immunologic; D000894:Anti-Inflammatory Agents, Non-Steroidal; D001190:Arylsulfonates; D012694:Serine; D001554:Benzene; C467259:phenylserine