Synthesis and anti-platelet, anti-inflammatory and anti-allergic activities of methoxyisoflavanquinone and related compounds.
In a continuation of our search for novel anti-platelet agents, isoflavone quinone and isoflavanquinone were selected as lead compounds and the synthesis of their methoxy derivatives was carried out. Among them, the 4'- and 7-methoxy derivatives were successfully prepared, whereas the attempt to obtain 3'-methoxy derivatives resulted in their isomers, 3'-methoxyflavone quinone and 3'-methoxyflavanquinone, instead. After screening for their anti-platelet, anti-inflammatory and anti-allergic activities, a preliminary structure-activity relationship was established. Compounds 6c, 7a-c, 8c and 9a-c were found to exhibit significant activities. In particular, compound 7c demonstrated very potent anti-platelet, anti-inflammatory and anti-allergic activities and was then recommended for further pharmacological investigation.
Chang
C Y
CY
Graduate Institute of Pharmaceutical Chemistry, China Medical College, Taichung, Taiwan, ROC.
Huang
L J
LJ
Wang
J P
JP
Teng
C M
CM
Chen
S C
SC
Kuo
S C
SC
D000818:Animals; D018926:Anti-Allergic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001792:Blood Platelets / Q000187:drug effects / Q000502:physiology; D015550:Cell Degranulation / Q000187:drug effects; D007529:Isoflavones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008297:Male; D008407:Mast Cells / Q000187:drug effects / Q000502:physiology; D009504:Neutrophils / Q000187:drug effects / Q000502:physiology; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011809:Quinones / Q000737:chemistry* / Q000494:pharmacology; D011817:Rabbits; D051381:Rats; D011918:Rats, Inbred SHR
D018926:Anti-Allergic Agents; D000893:Anti-Inflammatory Agents; D001578:Benzopyrans; D016227:Benzoquinones; D007529:Isoflavones; D010975:Platelet Aggregation Inhibitors; D011809:Quinones; C088068:claussequinone