Studies on o-[2,6-dichlorophenyl-1-amino] phenyl acetic acid. I. Synthesis, antiinflammatory, analgesic and ulcerogenic activities of some new amino acid conjugates.
o-[2,6-Dichlorophenyl-1-amino]phenyl acetic acid (diclofenac) (I) reacted with some amino acid esters, namely glycine, L-valine, L-diiodotyrosine and L-tryptophan through the active ester to give the corresponding o-[2,6-dichlorophenyl-1-amino]benzyl carboxy-N-amino acid ester of the type (IIa-d), respectively, which were hydrolysed in alkaline medium to yield the free amino acids (IIIa-d). Condensation of the latter compounds with hydrazine hydrate gave the corresponding acid hydrazides (IVa-d), which in turn were reacted with trimethoxybenzaldehyde to give the corresponding Schiff's bases (Va-d), respectively. The antiinflammatory, ulcerogenic and analgesic activities of the obtained compounds were also investigated.
Shalaby
A M
AM
Department of Tanning and Protein Chemistry, National Research Centre, Dokki, Cairo, Egypt.
el-Eraky
W
W
D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002351:Carrageenan; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D010147:Pain Measurement; D010648:Phenylacetates / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D010998:Pleurisy / Q000139:chemically induced / Q000517:prevention & control; D051381:Rats; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013276:Stomach Ulcer / Q000139:chemically induced* / Q000473:pathology
D000700:Analgesics; D000894:Anti-Inflammatory Agents, Non-Steroidal; D010648:Phenylacetates; D002351:Carrageenan