Synthesis of New 3-(2-Chloroquinolin-3-yl)-5-Phenylisoxazole Derivatives via Click-Chemistry Approach

被引：10

作者：

Fernandez-Galleguillos, Carlos ^{[1
]}

Saavedra, Luis A. ^{[1
]}

Gutierrez, Margarita ^{[1
]}

机构：

[1] Univ Talca, Inst Quim Recursos Nat, Lab Sintesis Organ, Talca 3460000, Chile

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2014年 / 25卷 / 02期

关键词：

quinoline; isoxazol; 1,3-dipolar cycloaddition; click chemistry; IN-VITRO; LIBRARY; BINDING; AZOLES; DRUG;

D O I：

10.5935/0103-5053.20140002

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we report the synthesis of new substituted 3-(2-chloroquinolin-3-yl)-5-phenylisoxazole (3a-j) by click chemistry in good to moderate yields. This approach is based on the regioselective copper(I)-catalyzed cycloaddition between different nitrile oxides derived from 2-chloroquinoline-3- carbaldehyde (2a-j) and phenylacetylene. Finally these derivatives were screened for their antibacterial evaluation in vitro against three Gram-negative clinical bacteria: Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii using standard methods.

引用

页码：365 / 371

页数：7

共 50 条

[41] Synthesis, Molecular Docking, In Silico ADME Predictions, and Toxicity Studies of N-Substituted-5-(4-Chloroquinolin-2-yl)-1,3,4-Thiadiazol-2-Amine Derivatives as COVID-19 Inhibitors
Mohamed, Hanaa S.
El-Serwy, Walaa S.
El-Serwy, Weam S.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2021, 47 (01) : 158 - 165
[42] Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)--carboline Derivatives
Brand, George
Gomes, Carla M. B.
Costa, Willian F.
Foglio, Mary A.
Ruiz, Ana L. T. G.
Sarragiotto, Maria H.
SYNTHESIS-STUTTGART, 2019, 51 (02): : 573 - 577
[43] Synthesis and Characterization of New Functionalized 1,2,3-Triazole-Based Acetaminophen Derivatives via Click Chemistry from Expired Commercial Acetaminophen Tablets
Kouznetsov, Vladimir V.
Lamus, Daniela Calderon
Galvis, Carlos E. Puerto
REACTIONS, 2023, 4 (03): : 329 - 341
[44] Synthetic approach to new 2H-benzo[b] [1,4]oxazin-3-one derivatives containing 1,2,3-triazole by click chemistry
Darifa, Addichi
Aziz, Ihammi
Saliha, Loughmari
Khalid, Abdelmouna
Mohamed, Ellouz
Mohammed, Chigr
TETRAHEDRON, 2024, 162
[45] Synthesis and molecular structure of 3-[5-(quinolin-2-yl)penta-1,4-dien-1-yl]-1,4-benzodioxin-2-one
V. V. Tkachev
Yu. A. Sayapin
I. V. Dorogan
V. S. Gorkovets
A. A. Kolodina
V. N. Komissarov
G. V. Shilov
S. M. Aldoshin
V. I. Minkin
Russian Journal of Organic Chemistry, 2013, 49 : 439 - 445
[46] Synthesis and antitumor activity of novel 1-substituted phenyl 3-(2-oxo-1,3,4-oxadiazol-5-yl) β-carbolines and their Mannich bases
Savariz, Franciele Cristina
Foglio, Mary Ann
Goes Ruiz, Ana Lucia T.
da Costa, Willian Ferreira
Silva, Marina de Magalhaes
Caldas Santos, Josue Carinhanha
Figueiredo, Isis Martins
Meyer, Emerson
de Carvalho, Joao Ernesto
Sarragiotto, Maria Helena
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (24) : 6867 - 6875
[47] Synthesis, docking study, and DNA photocleavage activity of some pyrimidinyl hydrazones and 3-(quinolin-3-yl)-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidine derivatives
Ajay Sharma
Vinod Kumar
Rajshree Khare
Girish Kumar Gupta
Vikas Beniwal
Medicinal Chemistry Research, 2015, 24 : 1830 - 1841
[48] Synthesis and Determination of Physicochemical Properties of New 3-(4-Arylpiperazin-1-yl)-2-hydroxypropyl 4-Alkoxyethoxybenzoates
Marvanova, Pavlina
Padrtova, Tereza
Odehnalova, Klara
Hosik, Ondrej
Oravec, Michal
Mokry, Petr
MOLECULES, 2016, 21 (12)
[49] Synthesis of 5-(1,2,3-triazol-4-yl)-2'deoxyuridines by a click chemistry approach: Stacking of triazoles in the major groove gives increased nucleic acid duplex stability
Kocalka, Petr
Andersen, Nicolai K.
Jensen, Frank
Nielsen, Poul
CHEMBIOCHEM, 2007, 8 (17) : 2106 - 2116
[50] Synthesis, Characterization and Antimicrobial Evaluation of Novel Imidazo[1,2-a]pyrazine-linked 1,2,3-Triazole Derivatives via a Click Chemistry Approach
Parmar, R. V.
Vadodaria, M. S.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (11) : 1927 - 1939

← 1 2 3 4 5 →