Quinoline and quinolone dimers and their biological activities: An overview

Rossiter, 2017, Natural products as platforms to overcome antibiotic resistance, Chem. Rev., 117, 12415, 10.1021/acs.chemrev.7b00283 Fernández-Álvaro, 2016, Antimalarial chemotherapy: natural product inspired development of preclinical and clinical candidates with diverse mechanisms of action, J. Med. Chem., 59, 5587, 10.1021/acs.jmedchem.5b01485 Zhang, 2018, Ciprofloxacin derivatives and their antibacterial activities, Eur. J. Med. Chem., 146, 599, 10.1016/j.ejmech.2018.01.078 Zhang, 2018, 4-Quinolone derivatives and their activities against Gram positive pathogens, Eur. J. Med. Chem., 144, 710, 10.1016/j.ejmech.2017.11.082 Hu, 2017, 4-Quinolone hybrids and their antibacterial activities, Eur. J. Med. Chem., 141, 335, 10.1016/j.ejmech.2017.09.050 Upadhyay, 2018, Synthesis and biological screening of pyrano[3,2-c]quinoline analogues as anti-inflammatory and anticancer agents, ACS Med. Chem. Lett., 9, 283, 10.1021/acsmedchemlett.7b00545 Sharma, 2013, Insight view on possible role of fluoroquinolones in cancer therapy, Curr. Top. Med. Chem., 13, 2076, 10.2174/15680266113139990133 Zhang, 2017, Synthesis, structure-activity relationships and preliminary mechanism of action of novel water-soluble 4-quinolone-3-carboxamides as antiproliferative agents, Eur. J. Med. Chem., 140, 239, 10.1016/j.ejmech.2017.09.017 Cannalire, 2016, A journey around the medicinal chemistry of hepatitis C virus inhibitors targeting NS4B: from target to preclinical drug candidates, J. Med. Chem., 59, 16, 10.1021/acs.jmedchem.5b00825 Fan, 2018, Fluoroquinolone derivatives and their anti-tubercular activities, Eur. J. Med. Chem., 146, 554, 10.1016/j.ejmech.2018.01.080 Zhang, 2017, Triazole derivatives and their anti-tubercular activity, Eur. J. Med. Chem., 138, 501, 10.1016/j.ejmech.2017.06.051 Xu, 2017, Isatin hybrids and their anti-tuberculosis activity, Chin. Chem. Lett., 2, 159, 10.1016/j.cclet.2016.07.032 Hu, 2017, Quinoline hybrids and their antiplasmodial and antimalarial activities, Eur. J. Med. Chem., 139, 22, 10.1016/j.ejmech.2017.07.061 Fan, 2018, Antiplasmodial and antimalarial activities of quinolone derivatives: an overview, Eur. J. Med. Chem., 146, 1, 10.1016/j.ejmech.2018.01.039 Sekgota, 2017, Application of the morita-baylis-hillman reaction in the synthesis of 3-[(N-Cycloalkylbenzamido)methyl]-2-Quinolones as potential HIV-1 integrase inhibitors, Bioorg. Chem., 75, 310, 10.1016/j.bioorg.2017.09.015 Luo, 2010, Development of integrase inhibitors of quinolone acid derivatives for treatment of AIDS: an overview, Mini Rev. Med. Chem., 10, 1046, 10.2174/1389557511009011046 Wang, 2018, Design, synthesis, and evaluation of orally bioavailable quinoline-indole derivatives as innovative multitarget-directed ligands: promotion of cell proliferation in the adult murine Hippocampus for the treatment of alzheimer's disease, J. Med. Chem., 61, 1871, 10.1021/acs.jmedchem.7b01417 Ren, 2018, Bis-coumarin derivatives and their biological activities, Curr. Top. Med. Chem., 18, 101, 10.2174/1568026618666180221114515 Gao, 2018, Recent developments of quinolone-based derivatives and their activities against Escherichia coli, Eur. J. Med. Chem., 157, 1223, 10.1016/j.ejmech.2018.08.095 Gao, 2018, Quinolone derivatives and their activities against methicillin-resistant Staphylococcus aureus (MRSA), Eur. J. Med. Chem., 157, 1081, 10.1016/j.ejmech.2018.08.061 Jiang, 2018, 4-Quinolone derivatives and their activities against Gram-negative pathogens, J. Heterocycl. Chem., 55, 2003, 10.1002/jhet.3244 Albecht, 1973, Antibacterial activity of quinolone carboxylic acids. III. Methyl-1-ethyl-4-quinolone-3-carboxylates and some -3-sucstituted quinonones, Chem. Ther., 8, 45 Chepyala, 2011, Quinolone dimers as potential antibacterial agents, Lett. Org. Chem., 8, 637, 10.2174/157017811799304322 Panda, 2015, Novel antibacterial active quinolone-fluoroquinolone conjugates and 2D-QSAR studies, Bioorg. Med. Chem. Lett, 25, 3816, 10.1016/j.bmcl.2015.07.077 Kerns, 2003, Piperazinyl-linked fluoroquinolone dimers possessing potent antibacterial activity against drug-resistant strains of Staphylococcus aureus, Bioorg. Med. Chem. Lett, 13, 1745, 10.1016/S0960-894X(03)00208-7 Kerns, 2003, Structural features of piperazinyl-linked ciprofloxacin dimers required for activity against drug-resistant strains of Staphylococcus aureus, Bioorg. Med. Chem. Lett, 13, 2109, 10.1016/S0960-894X(03)00376-7 Gould, 2004, Ciprofloxacin dimers target gyrase in Streptococcus pneumoniae, Antimicrob. Agents Chemother., 48, 2108, 10.1128/AAC.48.6.2108-2115.2004 Kerns, 2006, Susceptibility studies of piperazinyl-cross-linked fluoroquinolone dimers against test strains of Gram-positive and Gram-negative bacteria, Diagn. Microbiol. Infect. Dis., 54, 305, 10.1016/j.diagmicrobio.2005.11.004 Zhao, 2006, Bactericidal activity and target preference of a piperazinyl-cross-linked ciprofloxacin dimer with Staphylococcus aureus and Escherichia coli, J. Antimicrob. Chemother., 58, 1283, 10.1093/jac/dkl388 Ross, 2015, Synthesis of ciprofloxacin dimers for evaluation of bacterial permeability in atypical chemical space, Bioorg. Med. Chem. Lett, 25, 3468, 10.1016/j.bmcl.2015.07.010 Tanaka, 2008, Bisphosphonated fluoroquinolone esters as osteotropic prodrugs for the prevention of osteomyelitis, Bioorg. Med. Chem., 16, 9217, 10.1016/j.bmc.2008.09.010 Fedorova, 1997, Synthesis and turbeculostatic activity of podands with fluoroquinolone fragments, Pharm. Chem. J., 31, 354, 10.1007/BF02464368 Panda, 2015, Novel antibacterial active quinolone-fluoroquinolone conjugates and 2D-QSAR studies, Bioorg. Med. Chem. Lett, 25, 3816, 10.1016/j.bmcl.2015.07.077 Kerns, 2003, Piperazinyl-linked fluoroquinolone dimers possessing potent antibacterial activity against drug-resistant strains of Staphylococcus aureus, Bioorg. Med. Chem. Lett, 13, 1745, 10.1016/S0960-894X(03)00208-7 Kerns, 2003, Structural features of piperazinyl-linked ciprofloxacin dimers required for activity against drug-resistant strains of Staphylococcus aureus, Bioorg. Med. Chem. Lett, 13, 2109, 10.1016/S0960-894X(03)00376-7 Gould, 2004, Ciprofloxacin dimers target gyrase in Streptococcus pneumonia, Antimicrob. Agents Chemother., 48, 2108, 10.1128/AAC.48.6.2108-2115.2004 Azém, 2011, Eur. J. Med. Chem., 46, 6025, 10.1016/j.ejmech.2011.10.014 Pintér, 2009, Synthesis and antimicrobial activity of ciprofloxacin and norfloxacin permanently bonded to polyethylene glycol by a thiourea linker, J. Antibiot., 62, 113, 10.1038/ja.2008.26 Plech, 2013, Synthesis and in vitro activity of 1,2,4-triazole-ciprofloxacin hybrids against drug-susceptible and drug-resistant bacteria, Eur. J. Med. Chem., 60, 128, 10.1016/j.ejmech.2012.11.040 Plech, 2015, Search for factors affecting antibacterial activity and toxicity of 1,2,4-triazole-ciprofloxacin hybrids, Eur. J. Med. Chem., 97, 94, 10.1016/j.ejmech.2015.04.058 Gao, 2018, Design, synthesis and antibacterial evaluation of 1-[(1r, 2S)-2-Fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione hybrids, Chem. Biodivers., 10.1002/cbdv.201800261 Ceylan, 2016, Microwave-assisted and conventional synthesis of novel antimicrobial 1,2,4-triazole derivatives containing nalidixic acid skeleton, Heterocycl. Commun., 22, 229, 10.1515/hc-2016-0019 Darehkordi, 2016, Design, synthesis and evaluation of antibacterial effects of a new class of piperazinylquinolone derivatives, J. Heterocycl. Chem., 53, 89, 10.1002/jhet.2391 Antonello, 1993, Synthesis and biological activity of new quinolone derivatives, Eur. J. Med. Chem., 28, 291, 10.1016/0223-5234(93)90146-6 Dubar, 2009, Enhancement of the antimalarial activity of ciprofloxacin using a double prodrug/bioorganometallic approach, J. Med. Chem., 52, 7954, 10.1021/jm901357n Bellot, 2010, Trioxaferroquines as new hybrid antimalarial drugs, J. Med. Chem., 53, 4103, 10.1021/jm100117e Matos, 2010, PRIMACENES: novel non-cytotoxic primaquine-ferrocene conjugates with anti-Pneumocystis carinii activity, MedChemCommun, 1, 199, 10.1039/c0md00082e Sultana, 2010, Synthesis, characterization, antibacterial, antifungal and immunomodulating activities of gatifloxacin-metal complexes, J. Mol. Struct., 969, 17, 10.1016/j.molstruc.2010.01.036 Patel, 2015, Inorg. Chem. Commun., 15, 248, 10.1016/j.inoche.2011.10.037 Ballouche, 2009, Iron metabolism: a promising target for antibacterial strategies, Recent Pat. Anti-Infect. Drug Discov., 4, 190, 10.2174/157489109789318514 Hood, 2012, Nutritional immunity: transition metals at the pathogen-host interface, Nat. Rev. Microbiol., 10, 525, 10.1038/nrmicro2836 Mjos, 2016, Characterization, and evaluation of the antimicrobial potential of copper(II) coordination complexes with quinolone and p-xylenyl-linked quinolone ligands, J. Inorg. Biochem., 162, 280, 10.1016/j.jinorgbio.2016.02.026 Liu, 2018, Recent advances of 2-Quinolone-based derivatives as anti-tubercular agents, Anti-Infect. Agents, 16, 4, 10.2174/2211352516666180215151216 Fan, 2018, Recent advances of fluoroquinolone-metal complexes and their antibacterial activities, World Notes on Antibiotics, 39, 194 Drevenšek, 2005, Mixed-valence Cu(II)/Cu(I) complex of quinolone ciprofloxacin isolated by a hydrothermal reaction in the presence of L-histidine: comparison of biological activities of various copper-ciprofloxacin compounds, J. Inorg. Biochem., 99, 432, 10.1016/j.jinorgbio.2004.10.018 Efthimiadou, 2006, Neutral and cationic mononuclear copper(II) complexes with enrofloxacin: structure and biological activity, J. Inorg. Biochem., 100, 1378, 10.1016/j.jinorgbio.2006.03.013 Sultana, 2010, J. Mol. Struct., 969, 17, 10.1016/j.molstruc.2010.01.036 Patel, 2015, DNA interaction and in-vitro antibacterial studies of fluoroquinolone based platinum(II) complexes, Inorg. Chem. Commun., 15, 248, 10.1016/j.inoche.2011.10.037 Sadeek, 2013, Synthesis, characterization, DFT modeling and antimicrobial studies on the Ti(IV), Y(III) and Ce(IV) ofloxacin solid complexes, J. Kor. Chem. Soc., 57, 574 Sadeek, 2011, Spectroscopic studies, thermal analyses and biological evaluation of new V(IV), Zr(IV) and U(VI) moxifloxacin complexes, J. Mol. Struct., 1006, 192, 10.1016/j.molstruc.2011.09.009 Sultana, 2013, spectroscopic, and biological evaluation of some levofloxacin metal complexes, Med. Chem. Res., 22, 1371, 10.1007/s00044-012-0132-9 Refat, 2007, Synthesis and characterization of norfloxacin-transition metal complexes (group 11, IB): spectroscopic, thermal, kinetic measurements and biological activity, Spectrochim. Acta, Part A, 68, 1393, 10.1016/j.saa.2006.12.078 Skyrianou, 2011, Nickel-quinolones interaction. Part 4-Structure and biological evaluation of nickel(II)-enrofloxacin complexes compared to zinc(II) analogues, J. Inorg. Biochem., 105, 63, 10.1016/j.jinorgbio.2010.09.007 Turel, 2003, Nteractions of oxovanadium(IV) and the quinolone family member-ciprofloxacin, J. Inorg. Biochem., 95, 199, 10.1016/S0162-0134(03)00123-5 El-Gamel, 2011, Structural characterization and antimicrobial activity evaluation of metal complexes of sparfloxacin, Spectrochim. Acta, Part A, 82, 414, 10.1016/j.saa.2011.07.072 Eswaran, 2009, Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety, Eur. J. Med. Chem., 44, 4367, 10.1016/j.ejmech.2009.06.031 Oza, 2011, Synthesis of some novel divalent transition metal complexes as antimicrobials, Chin. Chem. Lett., 22, 935, 10.1016/j.cclet.2011.01.025 David, 2010, Cancer: an old disease, a new disease or something in between?, Nat. Rev. Canc., 10, 728, 10.1038/nrc2914 Zink, 1999, Growth inhibition of human melanoma cells in nude mice by antisense strategies to the type 1 insulin-like growth factor receptor, Anticancer Res., 19, 4273 World Health Organization. reportWorld Cancer Report 2014. Geneva. World Health Organization. Cancer control: knowledge into action. http://www.who.int/cancer/modules/en/. Jemal, 2011, Global cancer statistics, CA Tumor J. Clin., 61, 69, 10.3322/caac.20107 Shewach, 2009, Introduction to cancer chemotherapeutics, Chem. Rev., 109, 2859, 10.1021/cr900208x Fan, 2018, Design, synthesis and in vitro anti-mycobacterial activities of propylene-tethered gatifloxacin-isatin hybrids, J. Heterocycl. Chem., 55, 791, 10.1002/jhet.3112 Musiol, 2017, An overview of quinoline as a privileged scaffold in cancer drug discovery, Expet Opin. Drug Discov., 12, 583, 10.1080/17460441.2017.1319357 Jia, 2017, Synthesis and in vitro antitumor activity of novel naphthyridinone derivatives, Chin. Chem. Lett., 28, 235, 10.1016/j.cclet.2016.07.024 Bendell, 2015, A phase 1 study of the sachet formulation of the oral dual PI3K/mTOR inhibitor BEZ235 given twice daily (BID) in patients with advanced solid tumors, Invest. N. Drugs, 33, 463, 10.1007/s10637-015-0218-6 Li, 2013, Design, synthesis and antitumour activity of bisquinoline derivatives connected by 4-oxy-3-fluoroaniline moiety, Eur. J. Med. Chem., 64, 62, 10.1016/j.ejmech.2013.04.001 Tang, 2016, Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety, Bioorg. Med. Chem. Lett, 26, 1794, 10.1016/j.bmcl.2016.02.037 Tang, 2018, Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 1,8-naphthyridin-2-one moiety, Eur. J. Med. Chem., 158, 201, 10.1016/j.ejmech.2018.08.066 Moret, 2009, Discovery of a new family of bis-8-hydroxyquinoline substituted benzylamines with pro-apoptotic activity in cancer cells: synthesis, structure-activity relationship, and action mechanism studies, Eur. J. Med. Chem., 44, 558, 10.1016/j.ejmech.2008.03.042 Madonna, 2010, Structure-activity relationships and mechanism of action of antitumor bis 8-hydroxyquinoline substituted benzylamines, Eur. J. Med. Chem., 45, 623, 10.1016/j.ejmech.2009.11.006 Zhang, 2018, Design, synthesis, and anti leukemia cells proliferation activities of pyrimidylaminoquinoline derivatives as DOT1L inhibitors, Bioorg. Chem., 80, 649, 10.1016/j.bioorg.2018.07.022 Zhang, 2008, Synthesis and in vitro cytotoxicity evaluation of 4-aminoquinoline derivatives, Biomed. Pharmacother., 62, 65, 10.1016/j.biopha.2007.04.007 Martirosyan, 2004, Differentiation-inducing quinolines as experimental breast cancer agents in the MCF-7 human breast cancer cell model, Biomed. Pharmacol., 68, 1729 Riou, 2002, Cell senescence and telomere shortening induced by a new series of specific G-quadruplex DNA ligands, Proc. Natl. Acad. Sci. U. S. A., 99, 2672, 10.1073/pnas.052698099 Xiong, 2015, Targeting G-quadruplex nucleic acids with heterocyclic alkaloids and their derivatives, Eur. J. Med. Chem., 97, 538, 10.1016/j.ejmech.2014.11.021 Deady, 2000, Synthesis and Antitumor Activity of Some Indeno[1,2-b]quinoline-based bis Carboxamides, Bioorg. Med. Chem., 8, 977, 10.1016/S0968-0896(00)00039-0 Hu, 2011, Design, synthesis and antitumor activity of C3/C3 bis-fluoroquonolones cross-linked with [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazole, Acta Pharm. Sin. B, 1, 172, 10.1016/j.apsb.2011.07.001 Hu, 2010, Synthesis and antitumor evaluation of C3/C3 fluoroquinolone dimers (I): tethered with a fused heterocyclic s-triazolo[2,1-b][1,3,4]thiadiazole, Chin. Chem. Lett., 21, 661, 10.1016/j.cclet.2010.01.037 Hu, 2010, Part II: design, synthesis and antitumor action of C3/C3 bisfluoroquinolones linked-cross 2,5-[1,3,4]oxadiazole, Acta Pharm. Sin., 45, 1012 Ahsan, 2014, Cytotoxic dimeric quinolone-terpene alkaloids from the root bark of Zanthoxylum rhetsa, Photochemistry, 103, 8, 10.1016/j.phytochem.2014.03.008 Xu, 2018, Quinolone-triazole hybrids and their biological activities, J. Heterocycl. Chem., 55, 1854, 10.1002/jhet.3234 Kaur, 2011, Synthesis, antiprotozoal, antimicrobial, β-hematin inhibition, cytotoxicity and methemoglobin (MetHb) formation activities of bis(8-aminoquinolines), Bioorg. Med. Chem., 19, 197, 10.1016/j.bmc.2010.11.036 Kaschula, 2002, Structure-activity relationships in 4-aminoquinoline antiplasmodials. The role of the group at the 7-position, J. Med. Chem., 45, 3531, 10.1021/jm020858u Dorn, 1995, Total synthesis of redox-active 1.4-naphthoquinones and their metabolites and their therapeutic use as antimalarial and schistomicidal agents, Nature, 374, 269, 10.1038/374269a0 Egan, 2000, Structure-function relationships in aminoquinolines: effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of β-hematin formation, and antiplasmodial activity, J. Med. Chem., 43, 283, 10.1021/jm990437l Solomon, 2007, Synthesis and antimalarial activity of side chain modified 4-aminoquinoline derivatives, J. Med. Chem., 50, 394, 10.1021/jm061002i Vennestrom, 1992, Bisquinolines. 1. N,N-Bis(7-chloroquinolin-4-yl)alkanediamines with potential against chloroquine-resistant malaria, J. Med. Chem., 35, 2129, 10.1021/jm00089a025 Vennerstrom, 1998, Bisquinolines. 2. Antimalarial N,N-Bis(7-chloroquinolin-4-yl)heteroalkanediamines, J. Med. Chem., 41, 4360, 10.1021/jm9803828 Srivastava, 1999, Synthesis of bisquinolines and their in vitro ability to produce methemoglobin in canine hemolysate, Bioorg. Med. Chem. Lett, 9, 653, 10.1016/S0960-894X(99)00058-X Ryckebusch, 2002, Parallel synthesis and anti-malarial activity of a sulfonamide library, Bioorg. Med. Chem. Lett, 12, 2595, 10.1016/S0960-894X(02)00475-4 Ryckebusch, 2004, Design, synthesis and antimalarial activity of a glyoxylylhydrazone library, Bioorg. Med. Chem. Lett, 14, 4439, 10.1016/j.bmcl.2004.06.056 Warhurst, 2007, Activity of piperaquine and other 4-aminoquinoline antiplasmodial drugs against chloroquine-sensitive and resistant blood-stages of Plasmodium falciparum Role of β-haematin inhibition and drug concentration in vacuolar water- and lipid-phases, Miochem. Pharmacol., 73, 1910, 10.1016/j.bcp.2007.03.011 Gemma, 2012, Optimization of 4-aminoquinoline/clotrimazole-based hybrid antimalarials: further structure-activity relationships, in vivo studies, and preliminary toxicity profiling, J. Med. Chem., 55, 6948, 10.1021/jm300802s Girault, 2001, Antiplasmodial activity and cytotoxicity of bis-, tris-, and tetraquinolines with linear or cyclic amino linkers, J. Med. Chem., 44, 1658, 10.1021/jm001096a Biot, 2004, Easily synthesized antimalarial ferrocene triazacyclononane quinoline conjugates, J. Organomet. Chem., 689, 4678, 10.1016/j.jorganchem.2004.04.036 Khan, 2009, Synthesis and antimalarial activities of cyclen 4-aminoquinoline analogs, Antimicrob. Agents Chemother., 53, 1320, 10.1128/AAC.01304-08 Chipeleme, 2007, Synthesis and biological evaluation of phenolic Mannich bases of benzaldehyde and (thio)semicarbazone derivatives against the cysteine protease falcipain-2 and a chloroquine resistant strain of Plasmodium falciparum, Bioorg. Med. Chem., 15, 273, 10.1016/j.bmc.2006.09.055 Videnović, 2014, Second generation steroidal 4-aminoquinolines are potent, dual-target inhibitors of the botulinum neurotoxin serotype A metalloprotease and P. falciparum malaria, J. Med. Chem., 57, 4134, 10.1021/jm500033r Maether, 2011, Synthesis and antiplasmodial activity of streptocyanine/peroxide and streptocyanine/4-aminoquinoline hybrid dyes, Org. Biomol. Chem., 9, 7400, 10.1039/c1ob06048a van Heerden, 2012, Synthesis and in vitro antimalarial activity of a series of bisquinoline and bispyrrolo[1,2a]quinoxaline compounds, Eur. J. Med. Chem., 55, 335, 10.1016/j.ejmech.2012.07.037 Kondaparla, 2017, Design, synthesis and in vitro antiplasmodial activity of some bisquinolines against chloroquine resistant strain, Chem. Biol. Drug Des., 89, 901, 10.1111/cbdd.12914 Singh, 2012, Docking and in vitro antimalarial evaluation of bifunctional hybrids derived from b-lactams and 7-chloroquinoline using click chemistry, Bioorg. Med. Chem. Lett, 22, 57, 10.1016/j.bmcl.2011.11.082 Kumar, 2010, Synthesis of new 4-aminoquinolines and quinoline-acridine hybrids as antimalarial agents, Bioorg. Med. Chem. Lett, 20, 7059, 10.1016/j.bmcl.2010.09.107 Ryckebusch, 2003, Synthesis and in Vitro and in Vivo Antimalarial Activity of N1-(7-Chloro-4-quinolyl)-1,4-bis(3-aminopropyl)piperazine Derivatives, J. Med. Chem., 46, 542, 10.1021/jm020960r Fielding, 2017, Modulation of antimalarial activity at a putative bisquinoline receptor in vivo using fluorinated bisquinolines, Chem. Eur J., 23, 6811, 10.1002/chem.201605099 Milner, 2011, Characterization of in vivo metabolites of WR319691, a novel compound with activity against Plasmodium falciparum, Eur. J. Drug Metab. Pharmacokinet., 36, 151, 10.1007/s13318-011-0047-8 Milner, 2011, Structure-activity relationships of 4-position diamine quinoline methanols as intermittent preventative treatment (IPT) against Plasmodium falciparum, J. Med. Chem., 54, 6277, 10.1021/jm200647u Hrycyna, 2014, Quinine dimers are potent inhibitors of the Plasmodium falciparum chloroquine resistance transporter and are active against quinoline-resistant P. Falciparum, ACS Chem. Biol., 9, 722, 10.1021/cb4008953 Schmidt, 2016, Bistacrine derivatives as new potent antimalarials, Bioorg. Med. Chem., 24, 3636, 10.1016/j.bmc.2016.06.003 Girault, 2000, Antimalarial, antitrypanosomal, and antileishmanial activities and cytotoxicity of bis(9-amino-6-chloro-2-methoxyacridines): influence of the linker, J. Med. Chem., 43, 2646, 10.1021/jm990946n Gorlitzer, 2006, Thieno[3,2-c]quinoline-4-yl-amines-synthesis and investigation of activity against malaria, Pharmazie, 61, 278 Ayad, 2001, Synthesis, antimalarial activity and inhibition of haem detoxification of novel bisquinolines, Bioorg. Med. Chem. Lett, 11, 2075, 10.1016/S0960-894X(01)00383-3 Cowman, 1997, Synthesis and activity of some antimalarial bisquinolinemethanols, Aust. J. Chem., 50, 1091, 10.1071/C97086 Raynes, 1996, Novel Bisquinolone antimalarials. Synthesis, andtimalarial activity, and inhibition of haem polymerization, Biochem. Palrmacol., 52, 551, 10.1016/0006-2952(96)00306-1 Raynes, 1995, Synthesis and activity of some antimalarial bisquinolone, J. Med. Chem., 38, 204, 10.1021/jm00001a026 Acharya, 2008, Synthesis and antimalarial evaluation of novel pyridine quinoline hybrids, Med. Chem. Res., 17, 487, 10.1007/s00044-008-9092-5 Karasawa, 2012, Quinolone analogs 11: synthesis of novel 4-Quinolone-3-carbohydrazide derivatives with antimalarial activity, J. Heterocycl. Chem., 49, 288, 10.1002/jhet.774 Rodrigues, 2007, Plasmodium berghei: In vitro and in vivo activity of dequalinium, Exp. Parasitol., 115, 19, 10.1016/j.exppara.2006.05.002 Aziz, 2018, Inhibition of CYP3A by antimalarial piperaquine and its metabolites in human liver microsomes with IVIV extrapolation, J. Pharmacol. Sci., 107, 1461, 10.1016/j.xphs.2018.01.009 World Health Organization, 2017 Xu, 2017, Recent advances of pyrazole-containing derivatives as anti-tubercular agents, Eur. J. Med. Chem., 139, 429, 10.1016/j.ejmech.2017.07.059 Gao, 2018, Design, synthesis and anti-mycobacterial activity evaluation of benzofuran-isatin hybrids, Eur. J. Med. Chem., 159, 277, 10.1016/j.ejmech.2018.09.049 Paul, 2012, Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents, Bioorg. Med. Chem. Lett, 22, 1643, 10.1016/j.bmcl.2011.12.119 Kalia, 2015, Synthesis and anti-tubercular activity of conformationally-constrained and bisquinoline analogs of TMC207, MedChemComm, 6, 1554, 10.1039/C5MD00131E Gemma, 2009, Development of antitubercular compounds based on a 4-quinolylhydrazone scaffold. Further structure-activity relationship studies, Bioorg. Med. Chem., 17, 6063, 10.1016/j.bmc.2009.06.051 Subhedar, 2017, Quinolidene based monocarbonyl curcumin analogues as promising antimycobacterial agents: synthesis and molecular docking study, Bioorg. Med. Chem. Lett, 22, 922, 10.1016/j.bmcl.2017.01.004 Fedorova, 1997, Synthesis and tubeculostatic activity of podands with fluoroquinolone fragments, Pharm. Chem. J. Engl. Trans., 31, 354, 10.1007/BF02464368 Malik, 2005, Lethality of quinolones against Mycobacterium smegmatis in the presence or absence of chloramphenicol, Antimicrob. Agents Chemother., 49, 2008, 10.1128/AAC.49.5.2008-2014.2005 Zhao, 2005, Synthesis and antimycobacterial evaluation of certain fluoroquinolone derivatives, Bioorg. Med. Chem., 13, 3921, 10.1016/j.bmc.2005.04.005 Nagesh, 2014, Synthesis and evaluation of anti-tubercular activity of 6-(4-substituted piperazin-1-yl)phenanthridine analogues, Eur. J. Med. Chem., 74, 333, 10.1016/j.ejmech.2014.01.005 Palit, 2009, Phase transfer catalyzed synthesis of bis-quinolines: antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation, Eur. J. Med. Chem., 44, 845, 10.1016/j.ejmech.2008.04.014 Fakhfakh, 2003, Synthesis and biological evaluation of substituted quinolines: potential treatment of Protozoal and retroviral Co-infections, Bioorg. Med. Chem., 11, 5013, 10.1016/j.bmc.2003.09.007 Martinez-Grueiro, 2005, Nematocidal and trichomonacidal activities of 2-substituted quinolines, Il Farmaco, 60, 219, 10.1016/j.farmac.2004.11.010 Tewari, 2000, Syntheses and antifilarial profile of 7-Chloro-4-(substituted amino) quinolines: a new class of antifilarial agents, Bioorg. Med. Chem. Lett, 10, 1409, 10.1016/S0960-894X(00)00255-9 Shibata, 2018, 1,3-Di(quinoline-2-yl)guanidine binds to GGCCCC hexanucleotide repeat DNA in C9ORF72, Bioorg. Med. Chem. Lett, 28, 2364, 10.1016/j.bmcl.2018.06.032 Khan, 2016, Discovery of antischistosomal drug leads based on tetraazamacrocyclic derivatives and their metal complexes, Antimicrob. Agents Chemother., 60, 5331, 10.1128/AAC.00778-16 Opsenica, 2012, The synthesis of 2,5-bis(4-amidinophenyl)thiophene derivatives providing submicromolar-range inhibition of the botulinum neurotoxin serotype A metalloprotease, Eur. J. Med. Chem., 53, 374, 10.1016/j.ejmech.2012.03.043 Nuss, 2010, Pharmacophore refinement guides the design of nanomolar-range botulinum neurotoxin serotype A light chain inhibitors, ACS Med. Chem. Lett., 1, 301, 10.1021/ml100056v Santos, 2015, Synthesis and evaluation of the anti-nociceptive and anti-inflammatory activity of 4-aminoquinoline derivatives, Bioorg. Med. Chem., 23, 4390, 10.1016/j.bmc.2015.06.029 Strekowski, 2003, Bis-4-aminoquinolines: novel triple-helix DNA intercalators and antagonists of immunostimulatory CpG-oligodeoxynucleotides, Bioorg. Med. Chem. Lett, 11, 1079, 10.1016/S0968-0896(02)00525-4 Bolognesi, 2007, Multi-target-directed drug design strategy: from a dual binding site acetylcholinesterase inhibitor to a trifunctional compound against Alzheimer's disease, J. Med. Chem., 50, 6446, 10.1021/jm701225u Fu, 2008, Promising anti-Alzheimer’s dimer bis(7)-tacrine reduces beta-amyloid generation by directly inhibiting BACE-1 activity, Biochem. Biophys. Res. Commun., 366, 631, 10.1016/j.bbrc.2007.11.068 Leon, 2013, Recent advances in the multitarget-directed ligands approach for the treatment of alzheimer's disease, Med. Res. Rev., 33, 139, 10.1002/med.20248 Sahu, 2013, Synthesis and in vitro study of antibacterial, antifungal activities of some novel bisquinolines, Med. Chem. Res., 22, 94, 10.1007/s00044-012-0011-4 El-Megharbel, 2015, Synthesis and molecular structure of moxifloxacin drug with metal ions as a model drug against some kinds of bacteria and Fungi1, Russ. J. Gen. Chem., 85, 2366, 10.1134/S1070363215100230 Refat, 2007, Synthesis and characterization of norfloxacin-transition metal complexes (group 11, IB): spectroscopic, thermal, kinetic measurements and biological activity, Spectrochim. Acta, Part A, 68, 1393, 10.1016/j.saa.2006.12.078