2-Arylmethyl-1, 4-benzoquinones. II. Novel Inhibitors of Platelet Aggregation : Synthesis and Pharmacological Evaluation
Two new series of 2-arylmethyl-1, 4-benzoquinones (2 and 3) were synthesized for evaluation of their pharmacological activities. These compounds showed significant inhibition of platelet aggregation and some of them possessed a protective effect against endothelial cell injury. Structure-activity re...
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| Published in | Chemical & pharmaceutical bulletin Vol. 45; no. 4; pp. 668 - 674 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
The Pharmaceutical Society of Japan
1997
Maruzen |
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| Abstract | Two new series of 2-arylmethyl-1, 4-benzoquinones (2 and 3) were synthesized for evaluation of their pharmacological activities. These compounds showed significant inhibition of platelet aggregation and some of them possessed a protective effect against endothelial cell injury. Structure-activity relationship studies indicated that 2b, 2d and 3b are potent inhibitors of platelet aggregation induced by arachidonic acid (AA) with an IC50 in the range of 1-10 μg/ml. Among them, 3b showed a significant inhibitory activity against endothelial cell injury caused by hydrogen peroxide (H2O2) at 1 μM. |
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| AbstractList | Two new series of 2-arylmethyl-1,4-benzoquinones (2 and 3) were synthesized for evaluation of their pharmacological activities. These compounds showed significant inhibition of platelet aggregation and some of them possessed a protective against endothelial cell injury. Structure-activity relationship studies indicated that 2b, 2d and 3b are potent inhibitors of platelet aggregation induced by arachidonic acid (AA) with an IC50 in the range of 1-10 micrograms/ml. Among them, 3b showed a significant inhibitory activity against endothelial cell injury caused by hydrogen peroxide (H2O2) at 1 microM. Two new series of 2-arylmethyl-1, 4-benzoquinones (2 and 3) were synthesized for evaluation of their pharmacological activities. These compounds showed significant inhibition of platelet aggregation and some of them possessed a protective effect against endothelial cell injury. Structure-activity relationship studies indicated that 2b, 2d and 3b are potent inhibitors of platelet aggregation induced by arachidonic acid (AA) with an IC50 in the range of 1-10 μg/ml. Among them, 3b showed a significant inhibitory activity against endothelial cell injury caused by hydrogen peroxide (H2O2) at 1 μM. |
| Author | MIYAZAKI, Tomoko MIYANO, Seiji SUZUKI, Kenji SATOH, Fumio SUMOTO, Kunihiro OGINO, Ryoko TATSUOKA, Toshio ISHIHARA, Takafumi |
| Author_xml | – sequence: 1 fullname: SUZUKI, Kenji – sequence: 2 fullname: TATSUOKA, Toshio – sequence: 3 fullname: ISHIHARA, Takafumi – sequence: 4 fullname: OGINO, Ryoko – sequence: 5 fullname: MIYAZAKI, Tomoko – sequence: 6 fullname: SATOH, Fumio – sequence: 7 fullname: MIYANO, Seiji – sequence: 8 fullname: SUMOTO, Kunihiro |
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| Keywords | Endothelial cell Enzyme Quinone Enzyme inhibitor Rabbit Anticoagulant Lagomorpha Oxygen heterocycle Morpholine derivatives In vitro Antiplatelet agent L-Lactate dehydrogenase Vertebrata Mammalia Cytoprotector Structure activity relation Animal Bicyclic compound Carboxamide Benzenic compound Aromatic compound Oxidoreductases Benzofuran derivatives Chemical synthesis |
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| References | 5) Goto G., Okamoto K., Okutani T., Imada I., Chem. Pharm. Bull., 33, 4422 (1985). 9) a) Abe M., Morita I., Murota S., PG LT Essent. Fatty Acids, 34, 69 (1988 2) Hamberg M., Svensson J., Samuelsson B., Proc. Natl. Acad. Sci. U.S.A., 72, 2994 (1975). 6) Smith W.E., J. Org. Chem., 37, 3972 (1972). 3) Shiraishi M., Kato K., Terao S., Ashida Y., Terashita Z., Kito G., J. Med. Chem., 32, 2214 (1989). 4) Syper L., Kloc K., Mlochowski J., Szulc Z., Synthesis, 1979, 521. 1) Suzuki K., Tatsuoka T., Murakami T., Ishihara T., Aisaka K., Inoue T., Ogino R., Kuroki M., Miyazaki T., Satoh F., Miyano S., Sumoto K., Chem. Pharm. Bull., 44, 139 (1996). 7) Johnson R.A., Nidy E.G., Aiken J.W., Crittenden N.J., Gorman R.R., J. Med. Chem., 29, 1461 (1986). b) Whorton A.R., Montogomery M.E., Kent R.S., J. Clin. Invest., 76, 295 (1985). 8) Born G.V.R., Nature (London), 194, 927 (1962). |
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| Snippet | Two new series of 2-arylmethyl-1, 4-benzoquinones (2 and 3) were synthesized for evaluation of their pharmacological activities. These compounds showed... Two new series of 2-arylmethyl-1,4-benzoquinones (2 and 3) were synthesized for evaluation of their pharmacological activities. These compounds showed... |
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| SubjectTerms | 1, 4-benzoquinone Animals anti-platelet aggregation arachidonic acid Arachidonic Acid - pharmacology Benzoquinones - chemistry Benzoquinones - pharmacology Biological and medical sciences Blood. Blood coagulation. Reticuloendothelial system endothelial cell Endothelium, Vascular - drug effects Endothelium, Vascular - metabolism hydrogen peroxide Hydrogen Peroxide - metabolism Male Medical sciences Pharmacology. Drug treatments Platelet Aggregation - drug effects Platelet Aggregation Inhibitors - chemical synthesis Rabbits Structure-Activity Relationship |
| Title | 2-Arylmethyl-1, 4-benzoquinones. II. Novel Inhibitors of Platelet Aggregation : Synthesis and Pharmacological Evaluation |
| URI | https://www.jstage.jst.go.jp/article/cpb1958/45/4/45_4_668/_article/-char/en https://www.ncbi.nlm.nih.gov/pubmed/9145502 https://search.proquest.com/docview/79002928 |
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