Polycyclic N-Heterocyclic Compounds, Part 77: Synthesis of [1]Benzothieno[3′,2′:2,3]oxepino[4,5-d]pyrimidines and Evaluation of Their Antiplatelet Aggregation Activity

REFERENCES

• Hirota , T. ; Matsushita , T. ; Sasaki , K. ; Kashino , S. New synthetic method of furo[3,2-f][1,7]naphthyridine skeleton . Heterocycles 1995 , 41 , 2565 – 2574 .
   Web of Science ®Google Scholar
• Sasaki , K. ; Rouf , A. S. S. ; Hirota , T. Syntheses of furo[2,3-h][1,6]naphthyridine and imidazo(or pyrimido)[2,1-f][1,6]naphthyridines with rearrangement . J. Heterocycl. Chem. 1996 , 33 , 49 – 52 .
   Web of Science ®Google Scholar
• Hirota , T. ; Tomita , K. ; Sasaki , K. ; Okuda , K. ; Yoshida , M. ; Kashino , S. Syntheses of fused furo(or thieno)[2,3-b]pyridine derivatives via Smiles rearrangement and cyclization . Heterocycles 2001 , 55 , 741 – 752 .
   Web of Science ®Google Scholar
• Okuda , K. ; Yoshida , M. ; Hirota , T. ; Sasaki , K. Improved synthesis of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce–Smiles rearrangement and subsequent formation to furo[2,3-c]isoquinoline . Chem. Pharm. Bull. 2010 , 58 , 363 – 368 .
   PubMed Web of Science ®Google Scholar
• For recent reports on our Truce–Smiles type rearrangement, see (a) Okuda , K. ; Watanabe , N. ; Hirota , T. ; Sasaki , K. A novel Truce–Smiles type rearrangement reaction of 4-(2-cyanovinyloxy)butanenitriles to give cycloalkeno[1,2-d]furo[2,3-b]pyridines . Tetrahedron Lett. 2010 , 51 , 903 – 906 ; (b) Okuda , K. ; Deguchi , H. ; Kashino , S. ; Hirota , T. ; Sasaki , K. Synthesis of 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and related compounds: Evaluation of their bronchodilator activity and effects on lipoprotein lipase mRNA expression . Chem. Pharm. Bull. 2010 , 58 , 685 – 689 ; (c) Okuda , K. ; Takechi , H. ; Hirota , T. ; Sasaki , K. Synthesis of 5-amino-1,2-dihydrofuro[2,3-b]pyrido[3′,2′:4,5]thieno[3,2-d]pyridines and related compounds: Evaluation of effects on lipoprotein lipase mRNA expression . Heterocycles 2011 , 83 , 1315 – 1328 .
   Web of Science ®Google Scholar
• Okuda , K. ; Takano , J. ; Hirota , T. ; Sasaki , K. Synthesis of 5-amino-1,2-dihydro[1]benzofuro[3,2-d]furo[2,3-b]pyridines and their transformations to related compounds . J. Heterocycl. Chem. 2012 , 49 , 281 – 287 .
   Web of Science ®Google Scholar
• Cheng , S. ; Zhang , X. ; Wang , W. ; Zhao , M. ; Zheng , M. ; Chang , H. W. ; Wu , J. ; Peng , S. A class of novel N-(3S-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-amino acid derivatives: Their synthesis, anti-thrombotic activity evaluation, and 3D QSAR analysis . Eur. J. Med. Chem. 2009 , 44 , 4904 – 4919 .
   PubMed Web of Science ®Google Scholar
• Zhang , X. ; Wang , W. ; Cheng , S. ; Zhao , M. ; Zheng , M. ; Chang , H. W. ; Wu , J. ; Peng , S. 2,3-Diamino acid modifying 3S-tetrahydroisoquinoline-3-carboxylic acids: Leading to a class of novel agents with highly unfolded conformation, selective in vitro antiplatelet aggregation, and potent in vivo anti-thrombotic activity . Bioorg. Med. Chem. 2010 , 18 , 1536 – 1554 .
   PubMed Web of Science ®Google Scholar
• Hsieh , P.-W. ; Chang , Y.-T. ; Chuang , W. Y. ; Shih , H.-C. ; Chiang , S.-Z. ; Wu , C.-C. The synthesis and biologic evaluation of anti-platelet and cytotoxic β-nitrostyrenes. Bioorg. Med. Chem. 2010, 18, 7621–7627.
   PubMed Web of Science ®Google Scholar
• Ihmaid , S. ; Al-Rawi , J. ; Bradley , C. Synthesis, structural elucidation and DNA-dependant protein kinase and antiplatelet studies of 2-amino-[5,6,7,8-mono and 7,8-di-substituted]-1,3-benzoxazines . Eur. J. Med. Chem. 2010 , 45 , 4934 – 4946 .
   PubMed Web of Science ®Google Scholar
• Wang , H. ; Peng , L. ; Zhao , M. ; Liu , J. ; Zhang , X. ; Wang , Y. ; Wu , J. ; Li , L. ; Peng , S. 2-Substituted (S)-2-(3,3-dimethyl-1-oxo-10,10a-dihydroimidazo[1,5-b]isoquinolin-2(1H,3H,5H)-yl)acetic acids: Conformational prediction, synthesis, antithrombotic and vasodilative evaluation . Bioorg. Med. Chem. 2011 , 19 , 871 – 882 .
   PubMed Web of Science ®Google Scholar
• Yao , K. ; Zhao , M. ; Zhang , X. ; Wang , Y. ; Li , L. ; Zheng , M. ; Peng , S. A class of oral N-[(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-N′-(amino-acid-acyl)hydrazine: Discovery, synthesis, in vitro antiplatelet aggregation/in vivo anti-thrombotic evaluation and 3D QSAR analysis . Eur. J. Med. Chem. 2011 , 46 , 3237 – 3249 .
   PubMed Web of Science ®Google Scholar
• Liu , G. ; Xu , J. ; Park , K. C. ; Chen , N. ; Zhang , S. ; Ding , Z. ; Wang , F. ; Du , H. Novel synthesis approach and antiplatelet activity evaluation of 6-alkylamino-2,4-dialkyl(aryl)thiopyrimidines . Tetrahedron 2011 , 67 , 5156 – 5161 .
   Web of Science ®Google Scholar
• Born , G. V. R. ; Cross , M. J. The aggregation of blood platelets . J. Physiol. 1963 , 168 , 178 – 195 .
   PubMed Web of Science ®Google Scholar