N-[7-Chloro-4-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]quinoline]-acetamide

被引:8
作者
Coghi, Paolo [1 ,2 ]
Ng, Jerome P. L. [2 ,3 ]
Nasim, Ali Adnan [2 ,3 ]
Wong, Vincent Kam Wai [2 ,3 ]
机构
[1] Macau Univ Sci & Technol, Sch Pharm, Macau 999078, Peoples R China
[2] Macau Univ Sci & Technol, State Key Lab Qual Res Chinese Med, Macau 999078, Peoples R China
[3] Macau Univ Sci & Technol, State Key Lab Qual Res Chinese Med, Dr Nehers Biophys Lab Innovat Drug Discovery, Macau 999078, Peoples R China
关键词
1,2,3-triazole; anticancer; aminoquinoline; hybrid compound; ANTIMALARIAL; HYBRIDS; DESIGN;
D O I
10.3390/M1213
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,2,3-triazole is a well-known biologically active pharmacophore constructed by the copper-catalyzed azide-alkyne cycloaddition. We herein reported the synthesis of 4-amino-7-chloro-based [1,2,3]-triazole hybrids via Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of 4-azido-7-chloroquinoline with an alkyne derivative of acetaminophen. The compound was fully characterized by Fourier-transform infrared (FTIR), proton nuclear magnetic resonance (H-1-NMR), carbon-13 nuclear magnetic resonance (C-13-NMR), heteronuclear single quantum coherence (HSQC), ultraviolet (UV) and high-resolution mass spectroscopies (HRMS). This compound was screened in vitro with different normal and cancer cell lines. The drug likeness of the compound was also investigated by predicting its pharmacokinetic properties.
引用
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页数:6
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共 19 条
[1]   Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues [J].
Aher, Nilkanth G. ;
Pore, Vandana S. ;
Mishra, Nripendra N. ;
Kumar, Awanit ;
Shukla, Praveen K. ;
Sharma, Aanchal ;
Bhat, Manoj K. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (03) :759-763
[2]   New Compounds Hybrids 1H-1,2,3-Triazole-Quinoline Against Plasmodium falciparum [J].
Boechat, Nubia ;
Ferreira, Maria de Lourdes G. ;
Pinheiro, Luiz C. S. ;
Jesus, Antonio M. L. ;
Leite, Milene M. M. ;
Junior, Carlos C. S. ;
Aguiar, Anna C. C. ;
de Andrade, Isabel M. ;
Krettli, Antoniana U. .
CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 84 (03) :325-332
[3]   A BOILED-Egg To Predict Gastrointestinal Absorption and Brain Penetration of Small Molecules [J].
Daina, Antoine ;
Zoete, Vincent .
CHEMMEDCHEM, 2016, 11 (11) :1117-1121
[4]   Synthesis and in vitro antitubercular activity of a series of quinoline derivatives [J].
de Souza, Marcus V. N. ;
Pais, Karla C. ;
Kaiser, Carlos R. ;
Peralta, Monica A. ;
Ferreira, Marcelle de L. ;
Lourenco, Maria C. S. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (04) :1474-1480
[5]   Synthesis of triazole-oxazolidinones via a one-pot reaction and evaluation of their antimicrobial activity [J].
Demaray, Jeffrey A. ;
Thuener, Jason E. ;
Dawson, Matthew N. ;
Sucheck, Steven J. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (17) :4868-4871
[6]   One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides [J].
Feldman, AK ;
Colasson, B ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (22) :3897-3899
[7]   Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds [J].
Guantai, Eric M. ;
Ncokazi, Kanyile ;
Egan, Timothy J. ;
Gut, Jiri ;
Rosenthal, Philip J. ;
Smith, Peter J. ;
Chibale, Kelly .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (23) :8243-8256
[8]   Drug-like properties and the causes of poor solubility and poor permeability [J].
Lipinski, CA .
JOURNAL OF PHARMACOLOGICAL AND TOXICOLOGICAL METHODS, 2000, 44 (01) :235-249
[9]   Synthesis of 4-aminoquinoline-1,2,3-triazole and 4-aminoquinoline-1,2,3-triazole-1,3,5-triazine Hybrids as Potential Antimalarial Agents [J].
Manohar, Sunny ;
Khan, Shabana I. ;
Rawat, Diwan S. .
CHEMICAL BIOLOGY & DRUG DESIGN, 2011, 78 (01) :124-136
[10]   Novel 4-aminoquinolines through microwave-assisted SNAr reactions:: a practical route to antimalarial agents [J].
Melato, Sergio ;
Coghi, Paolo ;
Basilico, Nicoletta ;
Prosperi, Davide ;
Monti, Diego .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (36) :6118-6123