Polycyclic N-Heterocyclic Compounds. Part 64: 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

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概要

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• Reaction of 1-(3-cyanopropoxy)-3,4-dihydronaphthalene-2-carbonitriles with potassium tert-butoxide gave 5-amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines via a Truce–Smiles rearrangement. The 5-amino group was transformed to the bromo derivatives which were allowed to react with aliphatic cyclic amines to produce amino derivatives. In contrast, a combination of imidazole and NaH gave a dihydrofuran ring cleaved product, the structure of which was confirmed by X-ray crystallographic analysis. Effects of the newly synthesized compounds on carbamylcholine chloride-induced contractions of trachea and lipoprotein lipase mRNA expression were also evaluated and found one promising bronchodilator.

• 公益社団法人　日本薬学会の論文

著者

• KASHINO Setsuo

  Department of Chemistry, Faculty of Science, Okayama University

• SASAKI Kenji

  Faculty of Pharmaceutical Sciences, Okayama University

• HIROTA Takashi

  Faculty of Pharmaceutical Sciences, Okayama University

• Hirota Takashi

  Faculty Of Pharmaceutical Sciences Okayama University:faculty Of Pharmaceutical Sciences Kumamoto Un

• Kashino Setsuo

  Department Of Chemistry Faculty Of Science Okayama University

• Okuda Kensuke

  Gifu Pharmaceutical University

• Deguchi Hiroshi

  Faculty of Pharmaceutical Sciences, Okayama University

• Sasaki Kenji

  Faculty Of Engineering University Of Yamanashi

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