192377-01-8

Upstream product

• 5680-79-5 glycine ethyl ester hydrochloride 
• 15307-86-5 [2-(2,6-dichloroanilino)phenyl]acetic acid 
• 104425-36-7 acetic acid N-oxysuccinimide ester 

Downstream Products

• 69630-31-5 acetylglycine 
• 192377-08-5 2-[2-(2,6-Dichloro-phenylamino)-phenyl]-N-hydrazinocarbonylmethyl-acetamide 
• 216875-90-0 (2-{2-[2-(2,6-dichloro-phenylamino)-phenyl]-acetylamino}-acetylamino)-acetic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and comparative anti-phlogistic potency of new proteinogenic amino acid conjugates of 2-[2,6-dichlorophenyl-1-amino]phenyl acetic acid 'Diclofenac'

New proteinogenic amino acids conjugates of 2-[2,6-dichlorophenyl-1-amino]phenyl acetic acid 'Diclofenac', [I] were synthesized. Glycine methyl ester and L-methionine ethyl ester were coupled with [I] via the active ester method to give the corresponding 2-[2,6-dichlorophenyl-1-amino]benzyl carboxy N-amino acid ester of the type [IIa, b], respectively, which were hydrolyzed in alkaline medium to yield the free amino acids [IIIa, b]. Condensation of IIIa with glycine methyl ester using a modified classical carbodiimide (DCCI) method gave the corresponding 'Diclofenac' glycylglycine methyl ester [IVa]. Hydrolysis of compounds IVa gives the corresponding acid Va. Thionation of compounds IIb and IVa by reaction with Lewesson's Reagent (LR), afforded the corresponding thio-analogues (VIa and IVb). Interestingly, while retaining considerable comparative anti-phlogistic activity (anti-inflammatory and analgesic), the synthesized candidates proved to be practically nonulcerogenic in rats.

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.