- Synthesis and structure-activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents
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5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)-thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate (5h), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds.
- Noguchi, Toshiya,Hasegawa, Masahiro,Tomisawa, Kazuyuki,Mitsukuchi, Morihiro
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p. 4729 - 4742
(2007/10/03)
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- A STUDY OF THE TAUTOMERISM OF 2- AND 4-ETHOXYCARBONYLTHIOLAN-3-ONES IMPLICATING STEREOCHEMICAL EFFECTS OF RING-SUBSTITUTION
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A series of 2- and 4-ethoxycarbonylthiolan-3-ones have been synthesized and studied by 1H NMR and IR spectroscopy.Under conditions of tautomeric equilibrium in tetrachloromethane solution the 4-ethoxycarbonylthiolan-3-ones are generally more enolized (40-
- DUUS, F.
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p. 2633 - 2640
(2007/10/02)
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