Abstract
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.
MeSH terms
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3T3 Cells
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Animals
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Bronchodilator Agents / chemical synthesis*
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Bronchodilator Agents / chemistry
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Bronchodilator Agents / pharmacology*
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Crystallography, X-Ray
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Furans / chemistry*
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Gene Expression Regulation, Enzymologic / drug effects*
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Heterocyclic Compounds
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Inhibitory Concentration 50
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Isoquinolines / chemical synthesis*
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Isoquinolines / chemistry
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Isoquinolines / pharmacology*
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Lipoprotein Lipase / metabolism*
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Mice
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Molecular Structure
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Polycyclic Compounds / chemistry*
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RNA, Messenger / metabolism
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Reverse Transcriptase Polymerase Chain Reaction
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Trachea / drug effects*
Substances
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Bronchodilator Agents
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Furans
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Heterocyclic Compounds
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Isoquinolines
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Polycyclic Compounds
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RNA, Messenger
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Lipoprotein Lipase