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
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
收藏
页码:365 / 371
页数:7
相关论文
共 50 条
  • [1] Synthesis and antirhinovirus activity of 3-(diethylamino)-5-phenylisoxazole derivatives
    Mazzei, M
    Garzoglio, R
    Balbi, A
    Grandi, T
    DeMontis, A
    Corrias, S
    LaColla, P
    FARMACO, 1996, 51 (05): : 351 - 359
  • [2] Synthesis and Antitubercular Screening of [(2-Chloroquinolin-3-yl)methyl] Thiocarbamide Derivatives
    Kumar, Suresh
    Upmanyu, Neeraj
    Afzal, Obaid
    Bawa, Sandhya
    CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 84 (05) : 522 - 530
  • [3] Synthesis and Antibacterial Activity Evaluation of (2-Chloroquinolin-3-yl)methyleneamino Guanidine Derivatives
    Gao, Zhimin
    Wang, Tiantian
    Li, Shenzhen
    Wan, Huiqi
    Wang, Gang
    Wu, Yinbin
    Deng, Xianqing
    Song, Mingxia
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (10) : 2484 - 2488
  • [4] Efficient synthesis of AB ring core of luotonin A derivatives: (2-chloroquinolin-3-yl)methanamine
    Roopan, Selvaraj Mohana
    Khan, F. Nawaz
    Jin, Jong Sung
    RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (02) : 443 - 451
  • [5] Efficient synthesis of AB ring core of luotonin A derivatives: (2-chloroquinolin-3-yl)methanamine
    Selvaraj Mohana Roopan
    F. Nawaz Khan
    Jong Sung Jin
    Research on Chemical Intermediates, 2012, 38 : 443 - 451
  • [6] Synthesis of meso-tetrakis(2-chloroquinolin-3-yl) porphyrins
    Amaravathi, Mandha
    Babu, Maradolla Mohan
    Chandramouli, Garimella
    ARKIVOC, 2007, : 148 - 153
  • [7] Synthesis of (2-chloroquinolin-3-yl)-1,3,4-thiadiazole-2-carboxamides
    A. N. Aksenov
    M. M. Krayushkin
    V. N. Yarovenko
    Russian Chemical Bulletin, 2021, 70 : 1131 - 1134
  • [8] Synthesis of (2-chloroquinolin-3-yl)-1,3,4-thiadiazole-2-carboxamides
    Aksenov, A. N.
    Krayushkin, M. M.
    Yarovenko, V. N.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (06) : 1131 - 1134
  • [9] Novel 3-((2-chloroquinolin-3-yl)methylene)indolin-2-one derivatives produce anticancer efficacy in ovarian cancer in vitro
    Karthikeyan, Chandrabose
    Amawi, Haneen
    Ashby, Charles R., Jr.
    Khare, Vishwa M.
    Jones, Veronica
    Moorthy, N. S. Hari Narayana
    Trivedi, Piyush
    Tiwari, Amit K.
    HELIYON, 2019, 5 (05)
  • [10] 3-[(2-chloroquinolin-3-yl)methyl]quinazolin-4(3H)-ones as potential larvicidal agents
    Roopan, Selvaraj Mohana
    Khan, Fazlur-Rahman Nawaz
    Jin, Jong Sung
    PAKISTAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2013, 26 (04) : 747 - 750