10.1021/jo00064a043
The study focuses on the synthesis and conformational analysis of a quinoline derivative (1), which is an orally active inhibitor of 5-lipoxygenase and a leukotriene antagonist. The key chemicals involved include 2-(chloromethyl)quinoline (4) and the substituted phenol 12, which are coupled in the final step to form the target compound. The phenol derivative 12 is synthesized from m-hydroxyacetophenone (8) through an aldol condensation with n-butyraldehyde, yielding an intermediate that is subsequently reduced to 12. The synthesis of 2-(chloromethyl)quinoline (4) involves converting quinaldine (2) to its N-oxide monohydrate (3) and then reacting it with benzenesulfonyl chloride. The final coupling of 4 and 12 is performed in DMF with anhydrous potassium carbonate as a base, yielding the desired compound 1 in high purity. The study also includes an X-ray crystallographic analysis and molecular mechanics computations to elucidate the conformation of the synthesized compound, revealing a structure where the quinoline and benzenoid rings are nearly perpendicular, providing insights into its potential therapeutic applications.
10.1248/cpb.34.1917
The research focused on the synthesis and conformational analysis of 1-Methyl-3,4-benzo-7-thia-2-azabicyclo[3.3.1]nonane 7-oxide, a novel tricyclic compound with potential antispasmodic activity. The compound was synthesized through the reaction of quinaldine with methylsulfinylmethyl carbanion, and its structure was elucidated using spectral data and chemical evidence. The conformational analysis was conducted using proton and carbon-13 nuclear magnetic resonance spectroscopy, along with molecular mechanics calculations, which indicated that the stable conformer has a chairthiane ring with an equatorial sulfoxy group. Key chemicals used in the process included quinaldine, methylsulfinylmethyl carbanion, dimethylsulfoxide (DMSO), Raney nickel for desulfurization, and various quinaldine derivatives. The research concluded that the synthesized compound and its derivatives adopt a chair conformation with an equatorial sulfoxy group, which was consistent with the observed NMR data and molecular mechanics calculations.
10.1002/ardp.19773100312
The study explores the synthesis of sulfonyl derivatives of Mannich bases derived from quinaldine, pyrrole, and phenol, which are investigated as chemical carriers for germicidal substances. The researchers utilized various sulfones, such as p-toluenesulfone, as starting materials and reacted them with Mannich bases through processes like condensation and addition reactions. Key compounds synthesized include 2-(2'-chinolyl)-1-dimethylamino-3-p-toluenesulfonyl-propan-hydrochlorid (7), 2-benzolsulfonylmethyl-5-dimethylaminomethyl-1-methyl-pyrrol-hydrochlorid (12a), and 3,5-dimethyl-2-morpholinomethyl-6-p-toluenesulfonylmethyl-phenol (15c). These compounds were characterized using techniques such as melting point determination, elemental analysis, and IR spectroscopy. The study aims to develop new chemical forms that can effectively transport germicidal agents, potentially enhancing their stability and application in pharmaceuticals.
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