Synthesis and antiplatelet, antiinflammatory and antiallergic activities of 2,3-disubstituted 1,4-naphthoquinones.
Modification of 2-acetamido-3-chloro-1,4-naphthoquinone, which has potent antiplatelet, antiallergic and antiinflammatory activities, led to a series of 2,3-disubstituted 1,4-naphthoquinones. Some of these compounds showed significant antiplatelet, antiallergic and antiinflammatory activities. Among them, 2-methoxy-3-chloro-1,4-naphthoquinone (15) and 2-ethoxy-3-chloro-1,4-naphthoquinone (17) exhibited potent inhibitory effects on neutrophil and mast cell degranulation. 2-Methoxy-1,4-naphthoquinone (20) and 2-ethoxy-1,4-naphthoquinone (21) exhibited potent inhibitory effect on neutrophil superoxide formation. These four compounds were thus selected for further evaluation.
Lien
J C
JC
Graduate Institute of Pharmaceutical Chemistry, China Medical College, Taichung, Taiwan, R.O.C.
Huang
L J
LJ
Wang
J P
JP
Teng
C M
CM
Lee
K H
KH
Kuo
S C
SC
D000818:Animals; D018926:Anti-Allergic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D015550:Cell Degranulation / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005966:Glucuronidase / Q000378:metabolism; D006636:Histamine Release / Q000187:drug effects; D066298:In Vitro Techniques; D008407:Mast Cells / Q000187:drug effects / Q000201:enzymology; D009113:Muramidase / Q000378:metabolism; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000201:enzymology; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D011817:Rabbits; D051381:Rats; D017207:Rats, Sprague-Dawley; D013481:Superoxides / Q000378:metabolism
D018926:Anti-Allergic Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D009285:Naphthoquinones; D010975:Platelet Aggregation Inhibitors; D013481:Superoxides; D009113:Muramidase; D005966:Glucuronidase