21141-35-5

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 923, 1984 DOI: 10.1016/S0040-4039(01)80063-0

InChI:InChI=1/C11H9NO3/c1-15-9-4-2-3-7-5-6-8(11(13)14)12-10(7)9/h2-6H,1H3,(H,13,14)

Upstream product

• 3033-80-5 8-methoxy-2-methylquinoline 
• 103854-64-4 8-methoxy-2-quinolinecarboxaldehyde 
• 1127-45-3 8-Hydroxyquinoline-N-oxide 
• 1571-30-8 8-hydroxy-quinoline-2-carboxylic acid 
• 78224-47-2 methyl 8-methoxyquinoline-2-carboxylate 
• 88-75-5 2-hydroxynitrobenzene 
• 6759-78-0 8-hydroxyquinoline-2-carbonitrile 
• 6686-05-1 C₁₀H₁₀NO₂⁽¹⁺⁾*CH₃O₄S^(1-) 
• 826-81-3 2-methyl-8-quinolinol 
• 70127-96-7 2-amino-3-methoxy-benzaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 92735-81-4 8-methoxyquinoline-2-carbonitrile 
• 110-86-1 pyridine 
• 78224-64-3 (E)-8-methoxy-2-styrylquinoline 

Downstream Products

• 852402-76-7 (S)-8-methoxyquinoline-2-carboxylic acid (1-phenylethyl)amide 
• 852402-97-2 (4aS,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-1-one 
• 852402-92-7 (4aR,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydropyrazino[1,2-a]quinolin-1-one 
• 852403-07-7 (4aS,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline 
• 852403-02-2 (4aR,1'S)-10-methoxy-3-(1-phenylethyl)-2,3,4,4a,5,6-hexahydro-1H-pyrazino[1,2-a]quinoline 
• 852402-81-4 (2R,3'S)-8-methoxy-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (1-phenylethyl)amide 
• 852402-86-9 (2S,3'S)-8-methoxy-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (1-phenylethyl)amide 
• 1571-30-8 8-hydroxy-quinoline-2-carboxylic acid 

Relevant academic research and scientific papers

Development of Potent Inhibitors of the Mycobacterium tuberculosis Virulence Factor Zmp1 and Evaluation of Their Effect on Mycobacterial Survival inside Macrophages

The enzyme Zmp1 is a zinc-containing peptidase that plays a critical role in the pathogenicity of Mycobacterium tuberculosis. Herein we describe the identification of a small set of Zmp1 inhibitors based on a novel 8-hydroxyquinoline-2-hydroxamate scaffold. Among the synthesized compounds, N-(benzyloxy)-8-hydroxyquinoline-2-carboxamide (1 c) was found to be the most potent Zmp1 inhibitor known to date, and its binding mode was analyzed both by kinetics studies and molecular modeling, identifying critical interactions of 1 c with the zinc ion and residues in the active site. The effect of 1 c on intracellular Mycobacterium survival was assayed in J774 murine macrophages infected with M. tuberculosis H37Rv or M. bovis BCG and human monocyte-derived macrophages infected with M. tuberculosis H37Rv. Cytotoxicity and genotoxicity were also assessed. Overall, inhibitor 1 c displays interesting in vitro antitubercular properties worthy of further investigation.

Enantiomerically pure hexahydropyrazinoquinolines as potent and selective dopamine 3 subtype receptor ligands

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Oriented crystallization of CuSO4·5H2O under a monolayer of a novel amphiphilic ligand, 8-hexadecyloxyquinaldic acid

A new amphiphilic ligand, 8-hexadecyloxyquinaldic acid (HQA), has been synthesized and the characteristics of its monolayer on pure water and on CuSO4 aqueous solution have been examined. The HQA monolayer can interact with copper ions in the subphase, and crystallization of CuSO4·5H2O is induced under the monolayer. In order to understand the relationship between the different states of the monolayer and the induced inorganic crystallization, several typical states of the monolayer were chosen in our experiment. The results show that, when the monolayer is in the gas or liquid phase, its ability to control the oriented crystallization is poor. However, rather than the most dense phase, the most favorable state for oriented crystallization is the one with an area per molecule A = 17.0 A2, which could be considered as a liquid solid phase. This is attributed to a coordination effect and lattice matching at the inorganic/organic interface. Our research suggests that the state of the monolayer is a very important factor during the process of induced oriented crystallization.

Preparation and characterization of Langmuir-Blodgett films of N-hexadecyl-8-hydroxy-2-quinolinecarboxamide and its lanthanum complex

A new amphiphilic ligand, N-hexadecyl-8-hydroxy-2-quinolinecarboxamide (HHQ), and its lanthanum complex La(HHQ)2, were synthesized and characterized by elemental analysis, IR and 1H NMR spectroscopy. The characteristics of the monolayer, Langmuir-Blodgett (LB) films and cast films of HHQ and La(HHQ)2 were investigated by different physical methods, including surface pressure-area isotherms, absorption and fluorescence spectra and low-angle X-ray diffraction analysis. The LB film of La(HHQ)2 has good vertical homogeneity and the in-plane conductivity parallel to the compression direction is found to be 3.85 × 10-5 Sm-1.

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