Literature DB >> 29080495

Application of the Morita-Baylis-Hillman reaction in the synthesis of 3-[(N-cycloalkylbenzamido)methyl]-2-quinolones as potential HIV-1 integrase inhibitors.

Khethobole C Sekgota1, Swarup Majumder1, Michelle Isaacs2, Dumisani Mnkandhla2, Heinrich C Hoppe3, Setshaba D Khanye4, Frederik H Kriel5, Judy Coates5, Perry T Kaye6.   

Abstract

A practicable six-step synthetic pathway has been developed to access a library of novel 3-[(N-cycloalkylbenzamido)methyl]-2-quinolones using Morita-Baylis-Hillman methodology. These compounds and their 3-[(N-cycloalkylamino)methyl]-2-quinolone precursors have been screened as potential HIV-1 integrase (IN) inhibitors. A concomitant survey of their activity against HIV-1 protease and reverse-transcriptase reveals selective inhibition of HIV-1 IN.
Copyright © 2017 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  2-quinolones; Bioassay; HIV-1 integrase inhibitors; Morita_Baylis-Hillman; Synthesis

Mesh：

Substances：

Year:  2017        PMID： 29080495     DOI： 10.1016/j.bioorg.2017.09.015

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN： 0045-2068            Impact factor:   5.275


  9 in total

1.  A simple and convenient synthesis of 3-salicyloylquinoline-4-carboxylic esters from chromone and isatin.

Authors:  Xuequan Wang; Zhixin Yang; Weihang Miu; Pingting Ye; Mengjiao Bai; Suyue Duan; Xianfu Shen
Journal:  RSC Adv       Date:  2019-11-12       Impact factor: 4.036

2.  Total synthesis of quinolactacin-H from marine-derived Penicillium sp. ENP701 and biological activities.

Authors:  Jin-Xin Zhu; Yaojia Lu; Jun Chen; Jianwei Chen; Huawei Zhang; Xiaoze Bao; Xinyi Ye; Hong Wang
Journal:  RSC Adv       Date:  2020-06-25       Impact factor: 4.036

3.  Crystal structure and Hirshfeld surface analysis of hexyl 1-hexyl-2-oxo-1,2-di-hydro-quinoline-4-carboxyl-ate.

Authors:  Younos Bouzian; Sevgi Kansiz; Lhassane Mahi; Noureddine Hamou Ahabchane; Joel T Mague; Necmi Dege; Khalid Karrouchi; El Mokhtar Essassi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2020-04-09

4.  Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-chloro-ethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

Authors:  Sonia Hayani; Yassir Filali Baba; Tuncer Hökelek; Fouad Ouazzani Chahdi; Joel T Mague; Nada Kheira Sebbar; Youssef Kandri Rodi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-09-06

5.  Crystal structure, DFT study and Hirshfeld surface analysis of ethyl 6-chloro-2-eth-oxy-quinoline-4-carboxyl-ate.

Authors:  Younos Bouzian; Khalid Karrouchi; El Hassane Anouar; Rachid Bouhfid; Suhana Arshad; El Mokhtar Essassi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-05-31

6.  Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbamo-yl]-2-oxo-1,2-di-hydro-quinolin-1-yl}acetate.

Authors:  Yassir Filali Baba; Sonia Hayani; Tuncer Hökelek; Manpreet Kaur; Jerry Jasinski; Nada Kheira Sebbar; Youssef Kandri Rodi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-10-29

Review 7.  Recent Advances in One-Pot Modular Synthesis of 2-Quinolones.

Authors:  Wan Pyo Hong; Inji Shin; Hee Nam Lim
Journal:  Molecules       Date:  2020-11-20       Impact factor: 4.411

8.  Design, Synthesis, in vitro and in silico Characterization of 2-Quinolone-L-alaninate-1,2,3-triazoles as Antimicrobial Agents.

Authors:  Oussama Moussaoui; Rajendra Bhadane; Riham Sghyar; Janez Ilaš; El Mestafa El Hadrami; Said Chakroune; Outi M H Salo-Ahen
Journal:  ChemMedChem       Date:  2022-01-27       Impact factor: 3.540

9.  DFIQ, a Novel Quinoline Derivative, Shows Anticancer Potential by Inducing Apoptosis and Autophagy in NSCLC Cell and In Vivo Zebrafish Xenograft Models.

Authors:  Hurng-Wern Huang; Yung-Ding Bow; Chia-Yih Wang; Yen-Chun Chen; Pei-Rong Fu; Kuo-Feng Chang; Tso-Wen Wang; Chih-Hua Tseng; Yeh-Long Chen; Chien-Chih Chiu
Journal:  Cancers (Basel)       Date:  2020-05-25       Impact factor: 6.639
  9 in total

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