• Bulletin of the Korean Chemical Society
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• 제23권3호
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• pp.454-458
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• 2002

Furo[3,2-h]quinoline derivatives were synthesized as a gastric $H^+$/$K^+$-ATPase inhibitors. The oxycyclization of 7 and 8-positions in quinoline potentiated the inhibitory activity, while no significant changes in biological activity were observed by the variation of substituents in furan ring. The several furo[3,2-h]quinoline derivatives were worthy of in vivo investigation for their anti-secretory and anti-ulcer activity.

• Applied Biological Chemistry
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• 제34권1호
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• pp.43-48
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• 1991

Menaquinone과 비슷한 구조로써 새로운 quinoline 화합물들은 design하고 합성하여 submitochondria를 이용하여 생리활성을 검정하였다. NADH-ubiquinone oxidoreductase를 저해하는 생리활성은 주로 친유성 부분인 측쇄의 길이에 의존되었다. Quinoline핵의 3위치는 methyl group일 때가 가장 높은 저해활성을 나타냈다.

• Bulletin of the Korean Chemical Society
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• 제18권9호
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• pp.939-945
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• 1997

Several types of 4-substituted-quinoline-2-carboxylic acid derivatives possessing different substituents at C4-position such as sulfonyl, phosphonyl, carbonyl groups, or a flexible alkyl chain have been synthesized and evaluated for their in vitro antagonistic activity at the glycine site on the N-methyl-D-aspartate (NMDA) receptor. Of them, 5,7-dichloro-4-(tolylsulfonylamino)-quinoline-2-carboxylic acid 9 was found to have the best in vitro binding affinity with IC50 of 0.57 μM. On the other hand, in compounds 21 and 22 the introduction of flexible alkyl chains on C4 of the quinoline mother nuclei caused a significant decrease of the in vitro binding affinity. In addition, replacement of polar carboxylic acid group on C2 by neutral bioisosteres in compounds 23a-d also seems to be disadvantageous to in vitro activity. In the structure-activity relationship (SAR) study of the 4-substituted quinoline-2-carboxylic acid acid derivatives, it was realized that the substitution pattern on C4 significantly influences on the binding affinity for the glycine site of NMDA receptor and the binding affinity might be increased by the introduction of a suitable electron rich substituent at C4 which has the ability of H-bonding donor.

• Journal of Applied Biological Chemistry
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• 제58권1호
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• pp.5-8
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• 2015

This study was to isolate an active component of the chloroform fraction from the methanol extract of Ruta chalepensis leaves and to measure inhibitory effects against ${\alpha}$-glucosidase or ${\alpha}$-amylase. The inhibitory compound of R. chalepensis leaves was isolated using chromatographic methods and identified as quinoline. Quinoline and its structurally related derivatives were tested for their inhibitory activities by evaluating the $IC_{50}$ values against ${\alpha}$-amylase or ${\alpha}$-glucosidase and were compared with that of acarbose. Based on the $IC_{50}$ values, quinazoline exhibited the greatest inhibitory activity ($20.5{\mu}g/mL$), followed by acarbose ($66.5{\mu}g/mL$), and quinoline ($80.3{\mu}g/mL$) against ${\alpha}$-glucosidase. In case of ${\alpha}$-amylase, quinazoline had potent inhibitory activity, followed by quinoline ($179.5{\mu}g/mL$) and acarbose ($180.6{\mu}g/mL$). These results indicate that R. chalepensis extract, quinoline, and quinazoline could be useful for inhibiting ${\alpha}$-glucosidase or ${\alpha}$-amylase.

• Archives of Pharmacal Research
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• 제24권5호
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• pp.385-389
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• 2001

Twelve 4-substituted cyclopenta[c]quinoline derivatives were synthesized and evaluated in vitro cytotoxicity against four human cancer cell lines (HOP62, SK-OV-3, MD-MB-468 and T-47D). The compounds 6c and 6e bearing p-anisidine and pyrrolidine side chain were more active than the others.

• 약학회지
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• 제35권2호
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• pp.73-84
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• 1991

Quinoline, pyrazolo-[5, 4-b]-pyridine, isoxazolo-[5, 4-b]-pyridine, pyrazolo-[4, 3-c]-quinoline, isoxazolo-[5, 4-e]-thiazine, and isothiazolo-[5, 4-e]-thiazine derivatives were prepared as possible antiinflammatory agents. Some of the synthesized compounds showed antiinflammatory activities comparable to Aspirin and Naproxen.

• 대한화학회지
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• 제57권2호
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• pp.241-245
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• 2013

A series of novel quinoline-6-carboxamides and 2-chloroquinoline-4-carboxamides were synthesized by the reaction of their analogous carboxylic acids with various amine derivatives in the presence of base TEA and protecting agent BOP at room temperature. Synthesized compounds were confirmed by spectral characterization viz IR, $^1H$-NMR, and MS. Antibacterial activity carried out against Escherichia coli and Staphyllococcus aureus indicated that the synthesized compounds were active against these microorganisms.

• Food Science and Biotechnology
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• 제14권6호
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• pp.832-835
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• 2005

Inhibitory activity of active compound isolated from Ruta chalepensis leaf was examined against alcohol dehydrogenase and, upon comparison to those of four commercially available compounds (quinoline, quinoline-3-carboxaldehyde, quinoline-3-carboxylic acid, and quinoline-4-carboxylic acid) and 1,10-phenanthroline as alcohol dehydrogenase inhibitor, was characterized as quinoline-4-caboxaldehyde by spectral analyses. Inhibitory effects ($IC_{50}$) of quinoline-4-caboxaldehyde and quinoline derivatives varied depending on chemicals and concentrations used. The $IC_{50}$ values of quinoline-4-carboxaldehyde, quinoline-3-carboxaldehyde, quinoline, quinoline-3-carboxylic acid, and quinoline-4-carboxylic acid were 0.04, 0.3, 0.8, >1, and >1 mg/mL, respectively. These results suggest inhibitory action of quinoline-4-carboxaldehyde against alcohol dehydrogenase as prospective therapeutics for treatment of alcoholic liver diseases such as alcohol hepatitis and cirrhosis resulting from chronic alcohol abuse.

• 대한화학회지
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• 제55권5호
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• pp.805-807
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• 2011

The synthesis of different derivatives of isoxazolo[5,4-b]quinoline by the cyclization reaction of various substituted oximes of quinoline using mild base at ambient temperature. The formation of isoxazolo[5,4-b]quinoline, as a consequence of cheaper and more readily available $K_2CO_3$ and DMF participating in the reaction, is documented.

• 대한화학회지
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• 제66권3호
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• pp.194-201
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• 2022

A simple, efficient, and cost-effective method has been employed for the synthesis of 2,4,5-trisubstituted imidazole derivatives (3a-j) containing quinoline substituent at 2^nd position. Title compounds were obtained by multicomponent reaction (MCR), involving aryl substituted 1,2-diketone, quinoline carbaldehyde and ammonium acetate in the presence of acetic acid solvent under mild reaction conditions. The newly synthesized quinoline containing imidazole derivatives were confirmed through FT-IR, ¹H-NMR, ¹³C-NMR and mass spectral analysis. In-vitro microplate alamar blue assay (MABA) to determine the MIC (minimum inhibitory concentration) values against Mycobacterium tuberculosis H37Rv was performed for the synthesized compounds. The synthesized compounds exhibited activity against Mycobacterium tuberculosis and among which compounds, 3d, 3f and 3i showed good activity. The highest activity was showed with compound 3i. The anti-mycobacterial activity results are well correlated with the computational molecular docking analysis, which was performed for the synthesized compounds prior to the evaluation of the activity.