Synthesis and anti-inflammatory activity of some benzofuran and benzopyran-4-one derivatives.
New series of furosalicylic acids 3a-c, furosalicylanilides 6a-n, furobenzoxazines 8a-f, 1-benzofuran-3-arylprop-2-en-1-ones 12a,b, 6-(aryl-3-oxoprop-1-enyl)-4H-chromen-4-ones 16a-c and 6-[6-aryl-2-thioxo-2,5-dihydropyrimidin-4-yl]-4H-chromen-4-ones 17a-c were synthesized. Anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema model in rats and prostaglandin E(2) (PGE(2)) synthesis inhibition activity. Some of the tested compounds revealed comparable activity with less ulcerogenic effect than Diclofenac at a dose 100 mg/kg. All the synthesized compounds were docked on the active site of cyclooxygenase-2 (COX-2) enzyme and most of them showed good interactions with the amino acids of the active site comparable to the interactions exhibited by Diclofenac.
Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, El-Kasr El-Eini Street, Cairo 11562, Egypt.
Fatma Abd El-Fattah
FA
Ragab
Nahed Mahmoud
NM
Eid
Ghaneya Sayed
GS
Hassan
Yassin Mohammed
YM
Nissan
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D001572:Benzofurans / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D001578:Benzopyrans / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D001665:Binding Sites; D002351:Carrageenan; D020134:Catalytic Domain; D003198:Computer Simulation; D051546:Cyclooxygenase 2 / Q000737:chemistry; D004008:Diclofenac / Q000627:therapeutic use; D015232:Dinoprostone / Q000096:biosynthesis; D004195:Disease Models, Animal; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy*; D005786:Gene Expression Regulation / Q000187:drug effects; D008297:Male; D051381:Rats; D017208:Rats, Wistar
D000893:Anti-Inflammatory Agents; D001572:Benzofurans; D001578:Benzopyrans; D004008:Diclofenac; D002351:Carrageenan; D051546:Cyclooxygenase 2; D015232:Dinoprostone