[(Cycloalkylmethyl)phenyl]acetic acid derivatives and related compounds were synthesized to test their antiinflammatory and analgesic activities. Some of the compounds in this series were found to have good activity in the carrageenan edema test. Among them, sodium 2-[4-[(2-oxocyclopentyl)methyl] phenyl]propionate dihydrate (15) and 2-[4-[(2-oxocyclohexylidene)methyl]phenyl]propionic acid (13b) showed potent analgesic and antiadjuvant arthritis activities with excellent antipyretic properties.
The syntheses of 2-(D-alanylamino)-3-butanone (1), DL-5-[a-(D-alanylamino)ethyl]-l(2)fl'-tetrazole (2), and Dalanyl-D-alaninehydroxamic acid (3) are described.
Treatmentof 10-chloro-2,3,5,6,7,11b-hexahydro-7-methyl-11b-phenylbenzo [6,7] -1,4-diazepino [5,4-b]oxazol-6-one (IV) with sodium hydride in dimethyl acetamide gave the two compounds, 6-chloro-3-(2-hydroxyethyl)-1-methyl-4-phenyl-2(1H)-quinolone (V) and 6-chloro-3-hydroxy-1-methyl-4-pherryl-2(1H)-quinolone (VI). A mechanistic assumption for the formation of V was discussed.In the past few years, it has been reported that 1,4-benzodiazepines undergo rearrangements leading to isoindoles,1,3) indoles,4) quinazolines,5-7) quinoxalines8) and quinolines.9)In the preceding paper, we have reported1 on the base-catalyzed intramolecular rearrangements of benzo [6,7]-1,4-diazepino [5,4-b] oxazoles giving isoindole and acridanone derivatives, and on the reactions of I with N,N-dimethyl formamide (DMF) in the presence of sodium hydride affording exo-methylene compounds as shown in Chart 1. Our interest in the for-
1-Imidazolylalkyl-substituted di- or tetrahydrobenzo[b]thiophenecarboxylic acid derivatives and related compounds were synthesized from tetrahydrobenzo[b]thiophene derivatives (1 or 4) in order to study the structure-activity relationships of the inhibition of thromboxane A2 synthetase in vitro. Sodium 2-(1-imidazolylmethyl)-4,5-dihydrobenzo[b]thiophene-6-carboxylate (26) and 2-(1-imidazolylmethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-6-carbo xylic acid hydrochloride (28) showed the most potent and specific activity in vitro for thromboxane A2 synthetase inhibition.
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