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Paper | Regular issue | Vol 83, No. 6, 2011, pp.1315-1328
Published online, 12th April, 2011
DOI: 10.3987/COM-11-12187
Polycyclic N-Heterocyclic Compounds. Part 70: 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

Kensuke Okuda,* Hideyasu Takechi, Takashi Hirota, and Kenji Sasaki

*Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan

Abstract

Reaction of 3-(3-cyanopropoxy)thieno[2,3-b]pyridine-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2-dihydrofuro[2,3-b]pyrido[3’,2’:4,5]thieno[3,2-d]pyridines via a Truce-Smiles rearrangement. The 5-amino group was transformed to the chloro derivatives which were allowed to react with various nucleophiles. Effects of the newly synthesized compounds on lipoprotein lipase mRNA expression were also evaluated. The previously unreported parent compound, furo[2,3-b]pyrido[3’,2’:4,5]thieno[3,2-d]pyridine, was also synthesized.