5-芳酰基-6-(甲硫基)-1,2-二氢-3H-吡咯并[1,2-a]吡咯-1-羧酸和1-甲基-4-(甲硫基)-5-芳酰基吡咯-2-乙酸的合成及其抗炎和镇痛活性
Synthesis and antiinflammatory and analgesic activity of 5-aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-ca rboxyl ic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids.
作者信息
Muchowski J M, Galeazzi E, Greenhouse R, Guzmán A, Peréz V, Ackerman N, Ballaron S A, Rovito J R, Tomolonis A J, Young J M
机构信息
Syntex Research, Institute of Organic Chemistry, Palo Alto, California 94304.
出版信息
J Med Chem. 1989 Jun;32(6):1202-7. doi: 10.1021/jm00126a010.
5-Aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carb oxylic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids were synthesized and assayed as antiinflammatory and analgesic agents. The majority of these compounds exhibit a surprisingly low level of antiinflammatory activity (rat carrageenan paw) but have considerable potency as analgesics (mouse phenylquinone writing). For example, the p-tolyl-substituted bicyclic and monocyclic compounds 44 and 58 are 301 and 66 times more potent than aspirin (mouse writhing) but only 3.4 and 1.5 times more potent than phenylbutazone in the antiinflammatory screen (rat paw).
合成了5-芳酰基-6-(甲硫基)-1,2-二氢-3H-吡咯并[1,2-a]吡咯-1-羧酸和1-甲基-4-(甲硫基)-5-芳酰基吡咯-2-乙酸，并作为抗炎和镇痛剂进行了测定。这些化合物中的大多数表现出令人惊讶的低水平抗炎活性（大鼠角叉菜胶足肿胀实验），但作为镇痛药具有相当的效力（小鼠苯醌扭体实验）。例如，对甲苯基取代的双环和单环化合物44和58在镇痛方面（小鼠扭体实验）比阿司匹林强301倍和66倍，但在抗炎实验（大鼠足肿胀实验）中仅比保泰松强3.4倍和1.5倍。
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