Literature DB >> 31802783

Microwave-assisted, rapid synthesis of 2-vinylquinolines and evaluation of their antimalarial activity.

Guang Huang1, Claribel Murillo Solano2, Yuxin Su3,4, Nameer Ezzat1, Shino Matsui1, Liuyu Huang4, Debopam Chakrabarti2, Yu Yuan1.   

Abstract

A rapid and efficient synthesis of 2-vinylquinolines via trifluoromethanesulfonamidemediated olefination of 2-methylquinoline and aldehyde under microwave irradiation is reported. Biological evaluation of these scaffolds demonstrates that 2-vinylquinolines 3x - 3z possess excellent antimalarial activities against chloroquine-resistant Dd2 strain of Plasmodium falciparum (IC50 < 100 nM).

Entities:  

Keywords:  2-methylquinoline; 2-vinylquinoline; antimalarial; microwave-assisted synthesis; olefination

Year:  2019        PMID： 31802783      PMCID： PMC6892474          DOI： 10.1016/j.tetlet.2019.05.054

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  23 in total

1.  Structure-activity relationship of newly synthesized quinoline derivatives for reversal of multidrug resistance in cancer.

Authors:  T Suzuki; N Fukazawa; K San-nohe; W Sato; O Yano; T Tsuruo
Journal:  J Med Chem       Date:  1997-06-20       Impact factor: 7.446

2.  A catalyst-free benzylic C-H bond olefination of azaarenes for direct Mannich-like reactions.

Authors:  Yizhe Yan; Kun Xu; Yang Fang; Zhiyong Wang
Journal:  J Org Chem       Date:  2011-07-22       Impact factor: 4.354

3.  Regioselective Metal-Free Cross-Coupling of Quinoline N-Oxides with Boronic Acids.

Authors:  Luis Bering; Andrey P Antonchick
Journal:  Org Lett       Date:  2015-06-11       Impact factor: 6.005

4.  The structure of the blue luminescent delta-phase of tris(8-hydroxyquinoline)aluminium(III) (Alq3).

Authors:  Michael Cölle; Robert E Dinnebier; Wolfgang Brütting
Journal:  Chem Commun (Camb)       Date:  2002-12-07       Impact factor: 6.222

Review 5.  Biological activities of quinoline derivatives.

Authors:  Suresh Kumar; Sandhya Bawa; Himanshu Gupta
Journal:  Mini Rev Med Chem       Date:  2009-12       Impact factor: 3.862

6.  Metal-free oxidative olefination of primary amines with benzylic C-H bonds through direct deamination and C-H bond activation.

Authors:  Liang Gong; Li-Juan Xing; Tong Xu; Xue-Ping Zhu; Wen Zhou; Ning Kang; Bin Wang
Journal:  Org Biomol Chem       Date:  2014-09-14       Impact factor: 3.876

Review 7.  Leishmania treatment and prevention: Natural and synthesized drugs.

Authors:  Adnan A Bekhit; Eman El-Agroudy; Aliaa Helmy; Tamer M Ibrahim; Amin Shavandi; Alaa El-Din A Bekhit
Journal:  Eur J Med Chem       Date:  2018-10-11       Impact factor: 6.514

8.  The activities of current antimalarial drugs on the life cycle stages of Plasmodium: a comparative study with human and rodent parasites.

Authors:  Michael Delves; David Plouffe; Christian Scheurer; Stephan Meister; Sergio Wittlin; Elizabeth A Winzeler; Robert E Sinden; Didier Leroy
Journal:  PLoS Med       Date:  2012-02-21       Impact factor: 11.069

9.  4-Nitro styrylquinoline is an antimalarial inhibiting multiple stages of Plasmodium falciparum asexual life cycle.

Authors:  Bracken F Roberts; Yongsheng Zheng; Jacob Cleaveleand; Sukjun Lee; Eunyoung Lee; Lawrence Ayong; Yu Yuan; Debopam Chakrabarti
Journal:  Int J Parasitol Drugs Drug Resist       Date:  2017-02-21       Impact factor: 4.077

10.  Synthesis and biological evaluation of 2-styrylquinolines as antitumour agents and EGFR kinase inhibitors: molecular docking study.

Authors:  Magda A-A El-Sayed; Walaa M El-Husseiny; Naglaa I Abdel-Aziz; Adel S El-Azab; Hatem A Abuelizz; Alaa A-M Abdel-Aziz
Journal:  J Enzyme Inhib Med Chem       Date:  2018-12       Impact factor: 5.051
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  3 in total

1.  Synthesis, Structure-Activity Relationship, and Antimalarial Efficacy of 6-Chloro-2-arylvinylquinolines.

Authors:  Guang Huang; Claribel Murillo Solano; Joel Melendez; Justin Shaw; Jennifer Collins; Robert Banks; Arash Keshavarzi Arshadi; Rachasak Boonhok; Hui Min; Jun Miao; Debopam Chakrabarti; Yu Yuan
Journal:  J Med Chem       Date:  2020-10-06       Impact factor: 7.446

Review 2.  Triflamides and Triflimides: Synthesis and Applications.

Authors:  Mikhail Y Moskalik; Vera V Astakhova
Journal:  Molecules       Date:  2022-08-15       Impact factor: 4.927

3.  Acylacetylenes in multiple functionalization of hydroxyquinolines and quinolones.

Authors:  Kseniya V Belyaeva; Lina P Nikitina; Andrei V Afonin; Boris A Trofimov
Journal:  Tetrahedron       Date:  2020-08-20       Impact factor: 2.457
  3 in total

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