Antiinflammatory agents. 2. Syntheses and antiinflammatory activity of substituted 2-aminophenylacetic acid derivatives

Abstract

Several substituted 2-aminophenylacetic acid derivatives were prepared and tested for in vitro prostaglandin synthetase inhibition activity and for in vivo antiinflammatory activity. The 2-amino substituent is beneficial to potency in the inhibition of prostaglandin synthetase for the 3-phenoxy, 4-phenyl, and 3-benzoyl series, but only the 3-benzoyl series shows increased antiinflammatory potency in the in vivo assay.

Rhodium‐Catalyzed Boron Arylation of 1,2‐Azaborines

“…We identified felbinac as a suitable target for which the BN isostere can be readily accessed using our method. Felbinac is a topical nonsteroidal anti‐inflammatory drug (NSAID) and is used to treat rheumatic pain and inflammation 15. The two‐step synthesis of BN felbinac is illustrated in Scheme .…”

An Efficient Route to Novel Uracil-Based Drug-Like Molecules

“…Slightly better results were obtained with N-bromosuccinimide in carbon tetrachloride. [11][12][13] Moreover, only the bromine/carbon tetrachloride 14 conditions allowed for the convenient preparation of the target 3-bromomethylbenzophenones 4a-f with average isolated yields of around 70% (Table 2, entries 5-8). All the products were purified by short-column flash chromatography on silica, and NMR spectroscopy was used to confirm their purity, since nuclear bromination products are typical by-products of this method.…”

Friedel–Crafts Alkylation of N‐(2‐Chloropropionyl)aniline and the Generation Mechanism of Byproducts

“…A variety of methods for the synthesis of 3‐methylindolin‐2‐one have been reported. Friedel–Crafts alkylation of N ‐(2‐bromopropionyl)aniline and N ‐(2‐chloropropionyl)aniline in the presence of aluminum chloride were studied by Maged K. G. Mekhael and Kondo, respectively ; cyclization of N ′‐phenylisobutyrohydrazide to 3,3‐dimethylindolin‐2‐one was investigated by Paul Eastwood ; furthermore, James F. Wolfe claimed that N ‐(2‐chlorophenyl)propionamide can undergo smooth cyclization to afford the oxindole upon treatment with excess lithium diisopropylamide; Paul G. Gassman and David A. Walsh observed that 3‐methylindolin‐2‐one can be obtained by Raney nickel desulfurization of 3‐methyl‐3‐(methylthio)indolin‐2‐one ; Barry M. Trost found that treatment of indolin‐2‐one with butyllithium, then followed by nucleophilic substitution with methyl iodide yielded 3‐methylindolin‐2‐one; Balazs Volk obtained 3‐methylindolin‐2‐one by treatment of indolin‐2‐one with methanol in the presence of Raney nickel .…”