PMID: 7932579Oct 14, 1994Paper

Synthesis and structure-activity relationship of methyl-substituted indolo[2,3-b]quinolines: novel cytotoxic, DNA topoisomerase II inhibitors

Journal of Medicinal Chemistry
Wanda Peczynska-CzochJ Boratyński

Abstract

In furtherance of our SAR study on the chemistry and antitumor activity of fused nitrogen heteroaromatic compounds, a series of linear, methyl-substituted derivatives of 5H- and 6H-indolo[2,3-b]quinolines were synthesized according to the modified Graebe-Ullmann reaction. To establish the relationship between the physicochemical and biological activities of indolo[2,3-b]quinolines, their lipophilic properties, cytotoxic and antimicrobial activity, and ability to induce topoisomerase II dependent pSP65 DNA cleavage in vitro were investigated. We found that the antimicrobial and cytotoxic activity of indolo[2,3-b]quinolines was strongly influenced by the position, and the number of methyl substituents and the presence of methyl group at pyridine nitrogen was essential for the cytotoxicity of these compounds. All indolo[2,3-b]quinolines belonging to the 5H series, i.e., bearing a methyl group on the pyridine nitrogen, showed significant activity against procaryotic and eucaryotic organisms. They inhibited the growth of Gram-positive bacteria and pathogenic fungi at MIC range 3 x 10(-2) to 2.5 x 10(-1) mumol/mL, displayed cytotoxicity against KB cells ID50 in the range 2 x 10(-3) to 9 x 10(-3) mumol/mL, and stimulated the formation...Continue Reading

Citations

Apr 15, 2004·Bioorganic & Medicinal Chemistry Letters·Aurore PerzynaJean-Pierre Hénichart
Nov 1, 2000·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·K Kamieńska-TrelaJ Wójcik
May 12, 2012·Journal of Medicinal Chemistry·Katarzyna SidorykWanda Peczyńska-Czoch
Aug 1, 2012·The Journal of Organic Chemistry·Timothy K LaneJanis Louie
Jan 27, 2006·Organic Letters·Patricia Vera-LuqueJuan J Vaquero
Mar 12, 2011·Organic Letters·Rapolu Kiran KumarTharmalingam Punniyamurthy
Nov 29, 2005·Natural Product Reports·Tomomi Kawasaki, Kazuhiro Higuchi
Sep 28, 2012·Beilstein Journal of Organic Chemistry·Zhiyuan MaJohn K Snyder
Apr 2, 2014·European Journal of Medicinal Chemistry·Katarzyna SidorykŁukasz Kaczmarek
Sep 15, 2012·Biological & Pharmaceutical Bulletin·Anna JarominArkadiusz Kozubek
Feb 6, 2007·Bioorganic & Medicinal Chemistry·Kamel MetwallySusan Bane
Dec 5, 2006·European Journal of Medicinal Chemistry·Kamel MetwallyDimitris Kletsas
Feb 9, 2012·Chemistry, an Asian Journal·Tanmoy ChandaMaya Shankar Singh
Apr 28, 2012·Angewandte Chemie·Ashley L PumphreyTom G Driver
Nov 24, 2004·Bioorganic & Medicinal Chemistry·Yeh-Long ChenCherng-Chyi Tzeng
Nov 18, 2005·Biochemical and Biophysical Research Communications·Rihui CaoAnlong Xu
Mar 23, 2007·Bioorganic & Medicinal Chemistry Letters·Deborah L MoodyChristopher J Michejda
Jun 30, 2006·Bioorganic & Medicinal Chemistry·Ming ZhaoShiqi Peng
Oct 4, 2012·Bioorganic & Medicinal Chemistry Letters·E RajanarendarY N Reddy
Sep 5, 2012·Bioorganic & Medicinal Chemistry Letters·Wojciech LuniewskiLukasz Kaczmarek
Nov 21, 2009·European Journal of Medicinal Chemistry·Chiao-Li YangCherng-Chyi Tzeng
Apr 28, 2016·Organic & Biomolecular Chemistry·Zicong YanZhiyong Wang
Dec 21, 2004·International Journal of Cancer. Journal International Du Cancer·Qi ChenAnlong Xu
Sep 12, 2018·Chemical Communications : Chem Comm·Meng-Han TsaiRai-Shung Liu
Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Robert M GenganPalathurai S Mohan
Dec 21, 2018·Chemical Biology & Drug Design·Angel H RomeroAlvaro Morales
Jan 21, 2006·Magnetic Resonance in Chemistry : MRC·E BednarekL Kozerski
Jan 11, 2013·Chemical & Pharmaceutical Bulletin·Mohammed Salem Al-DosariYassin Mohammed Nissan
May 25, 2012·Organic & Biomolecular Chemistry·Arepalli Sateesh KumarRajagopal Nagarajan
Feb 12, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Jen-Chieh Hsieh

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