异色满酮-4及其衍生物的合成(Ⅳ)——辛可宁酸类似物的合成

Synthesis of Isochroman-4-one and Its Derivatives (Ⅳ)——Preparation of Analogues of Cinchophen

由异色满酮-4(1)与邻氨基苯甲醛或邻氨基胡椒醛进行Friedlender缩合反应得到异色满并喹啉衍生物异色满并[4,3-b]喹啉(2)和9,10-亚甲二氧基异色满并[4,3-b]喹啉(3)。由1与靛红系列物经Pfitzinger反应得到系列辛可宁酸类似物(4a～e)。这些化合物在结构上与抗炎药辛可芬类似,其中酯化产物7-乙氧甲酰基-9-甲基异色满并[4,3-b]喹啉(5)则与抗炎镇痛药新辛可芬相似。对7-羧基异色满并[4,3-b]喹啉(4a～d)进行药理试验发现具有显著的抗炎效果。采用小白鼠-巴豆油涂耳刺激法进行抗炎试验。

Isochromano-[4,3-b] quinoline(2) and 9,10-methylenedioxyisochromano-[4,3-b] quino- line (3) are obtained, respectively, by condensing isochromanone (1) with o-aminobenzaldehyde and o-amino piperonal in the presence of sodium ethoxide. The new derivatives of 7-carboxyisochromano [4,3-b] quinoline (4a-e) are obtained by the reaction of (1) with isatins in a satisfactory yield. Es-terification of (4c) can be transformed into (5) which has a new cinchophen-like structure. Compound (4a) and (5) show a good antiphlogistic activity.