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.
Subject(s)
Bronchodilator Agents/chemical synthesis , Bronchodilator Agents/pharmacology , Furans/chemistry , Gene Expression Regulation, Enzymologic/drug effects , Isoquinolines/chemical synthesis , Isoquinolines/pharmacology , Lipoprotein Lipase/metabolism , Polycyclic Compounds/chemistry , Trachea/drug effects , 3T3 Cells , Animals , Bronchodilator Agents/chemistry , Crystallography, X-Ray , Heterocyclic Compounds , Inhibitory Concentration 50 , Isoquinolines/chemistry , Mice , Molecular Structure , RNA, Messenger/metabolism , Reverse Transcriptase Polymerase Chain ReactionABSTRACT
The reaction of 3-(2-cyanophenyl)quinazolin-4(3H)-one with various primary alkylamines gave 3-alkylquinazolin-4(3H)-ones via an addition of the nucleophile, ring opening, and ring closure (ANRORC) mechanism. This type of reaction required hydroxy group functionality in either the solvent or reagent. When hydroxylamine was used as nitrogen nucleophile, the intermediate of this reaction was isolated and found to be an amide oxime. When ethylenediamine was used as the nucleophile, the amidine moiety of the intermediate decomposed to give a benzanilide.
Subject(s)
Amines/chemistry , Heterocyclic Compounds/chemical synthesis , Polycyclic Compounds/chemical synthesis , Quinazolinones/chemistry , Crystallography, X-Ray , Heterocyclic Compounds/chemistry , Models, Molecular , Molecular Structure , Polycyclic Compounds/chemistry , StereoisomerismABSTRACT
The title compound, [Co(C29H24N2O2)(C4H6N2)2]ClO4, contains an optically active tetradentate Schiff base ligand in an equatorial plane and two 1-methylimidazole ligands at apical positions. The central N-C-C-N chelate ring of the Schiff base ligand has an envelope structure with a lambda conformation, which is different from the solution structure predicted from circular dichroism and 1H NMR spectra.
