Chemistry Department of Natural Compounds, National Research Centre, Cairo, Egypt.
Acta Pharm. 2012 Mar;62(1):15-30. doi: 10.2478/v10007-012-0007-0.
Starting from N-substituted indole-3-carboxaldehydes (1a-g) a series of new 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles (3a-g and 4a-g) have been synthesized via the acid catalyzed condensation reaction of 1a-g with 3-amino-5-pyrazolone, followed by the reaction with arylidene malononitriles. A series of new 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles (7a-g) have been prepared either via the base catalyzed condensation reaction of 1a-g with 3-amino-5-pyrazolone to give 6a-g, followed by the reaction with malononitrile or by the reaction of N-substituted-3-indolylidene malononitriles (5a-g) with 3-amino-5-pyrazolone. According to the obtained results, the newly synthesized compounds possess significant anti-inflammatory, analgesic and anticonvulsant activities. The anticonvulsant potency of certain tested compounds was more pronounced than both anti-inflammatory and analgesic activities. Moreover, most of the newly synthesized compounds possess potential antimicrobial activity against Escherichia coli and Pseudomonas aeruginosa.
从 N-取代的吲哚-3-甲酰基（1a-g）出发，通过 1a-g 与 3-氨基-5-吡唑酮的酸催化缩合反应，然后与亚甲二氰基反应，合成了一系列新的 3-[(N-取代的吲哚-3-基)亚甲氨基]-6-氨基-4-芳基-吡喃（2,3-c）吡唑-5-甲腈（3a-g 和 4a-g）。通过 1a-g 与 3-氨基-5-吡唑酮的碱催化缩合反应得到 6a-g，然后与丙二腈反应，或者通过 N-取代的 3-吲哚基亚甲二氰基（5a-g）与 3-氨基-5-吡唑酮反应，制备了一系列新的 3,6-二氨基-4-（N-取代的吲哚-3-基）吡喃（2,3-c）吡唑-5-甲腈（7a-g）。根据获得的结果，新合成的化合物具有显著的抗炎、镇痛和抗惊厥活性。某些测试化合物的抗惊厥效力比抗炎和镇痛活性更为明显。此外，大多数新合成的化合物对大肠杆菌和铜绿假单胞菌具有潜在的抗菌活性。
