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

Alin, 1994, Concentration and time dependency of artemisinin efficacy against Plasmodium falciparum in vitro, Am. J. Trop. Med. Hyg., 50, 771, 10.4269/ajtmh.1994.50.771 Ashley, 2014, Spread of artemisinin resistance in Plasmodium falciparum malaria, N. Engl. J. Med., 371, 411, 10.1056/NEJMoa1314981 Avdeef, 2001, Physicochemical profiling (solubility, permeability and charge state), Curr. Top. Med. Chem., 1, 277, 10.2174/1568026013395100 Bennett, 2004, Novel, rapid, and inexpensive cell-based quantification of antimalarial drug efficacy, Antimicrob. Agents Chemother., 48, 1807, 10.1128/AAC.48.5.1807-1810.2004 Bon, 2010, Bioactivity-guided navigation of chemical space, Acc. Chem. Res., 43, 1103, 10.1021/ar100014h Bouillon, 2013, Screening and evaluation of inhibitors of Plasmodium falciparum merozoite egress and invasion using cytometry, Methods Mol. Biol., 923, 523, 10.1007/978-1-62703-026-7_36 Cordier, 2008, Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries, Nat. Product. Rep., 25, 719, 10.1039/b706296f Cui, 2011, WHO urges the phasing out of artemisinin based monotherapy for malaria to reduce resistance, BMJ, 342, d2793, 10.1136/bmj.d2793 Dahl, 2007, Multiple antibiotics exert delayed effects against the Plasmodium falciparum apicoplast, Antimicrob. Agents Chemother., 51, 3485, 10.1128/AAC.00527-07 Di, 2008, Applications of high throughput microsomal stability assay in drug discovery, Comb. Chem. High Throughput Screen., 11, 469, 10.2174/138620708784911429 Famin, 2002, Differential effects of 4-aminoquinoline-containing antimalarial drugs on hemoglobin digestion in Plasmodium falciparum-infected erythrocytes, Biochem. Pharmacol., 63, 393, 10.1016/S0006-2952(01)00878-4 Genis, 2012, A minimalist fragment approach for the design of natural-product-like synthetic scaffolds, Drug Discov. today, 17, 1170, 10.1016/j.drudis.2012.05.013 Gong, 2013, Preparation of 4-aminoquinazoline derivatives as antitumor agents, Faming Zhuanli Shenqing Goodman, 2007, The effects of anti-bacterials on the malaria parasite Plasmodium falciparum, Mol. Biochem. Parasitol., 152, 181, 10.1016/j.molbiopara.2007.01.005 Greenwood, 1995, Conflicts of interest: the genesis of synthetic antimalarial agents in peace and war, J. Antimicrob. Chemother., 36, 857, 10.1093/jac/36.5.857 Gupta, 2009, Identification of selective inhibitors of cancer stem cells by high-throughput screening, Cell, 138, 645, 10.1016/j.cell.2009.06.034 Hemphill, 2006, Nitazoxanide, a broad-spectrum thiazolide anti-infective agent for the treatment of gastrointestinal infections, Expert Opin. Pharmacother., 7, 953, 10.1517/14656566.7.7.953 Howard, 1981, Invasion of erythrocytes by malaria merozoites: evidence for specific receptors involved in attachment and entry, Ciba Found. Symp., 80, 202 Janiszewski, 2001, A high-capacity LC/MS system for the bioanalysis of samples generated from plate-based metabolic screening, Anal. Chem., 73, 1495, 10.1021/ac0013251 Johnson, 2007, Assessment and continued validation of the malaria SYBR green I-based fluorescence assay for use in malaria drug screening, Antimicrob. Agents Chemother., 51, 1926, 10.1128/AAC.01607-06 Kansy, 1998, Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes, J. Med. Chem., 41, 1007, 10.1021/jm970530e Kombarov, 2010, BioCores: identification of a drug/natural product-based privileged structural motif for small-molecule lead discovery, Mol. Divers., 14, 193, 10.1007/s11030-009-9157-5 Krishna, 2004, Artemisinins: mechanisms of action and potential for resistance, Drug Resistance Updates Rev. Comment. Antimicrob. Anticancer Chemother., 7, 233, 10.1016/j.drup.2004.07.001 Lambros, 1979, Synchronization of Plasmodium falciparum erythrocytic stages in culture, J. Parasitol., 65, 418, 10.2307/3280287 Lee, 2014, Discovery of carbohybrid-based 2-aminopyrimidine analogues as a new class of rapid-acting antimalarial agents using image-based cytological profiling assay, J. Med. Chem., 57, 7425, 10.1021/jm5009693 Loria, 1999, Inhibition of the peroxidative degradation of haem as the basis of action of chloroquine and other quinoline antimalarials, Biochem. J., 339, 363, 10.1042/bj3390363 Margolis, 2007, Assembly of 4-aminoquinolines via palladium catalysis: a mild and convenient alternative to SNAr methodology, J. Org. Chem., 72, 2232, 10.1021/jo062168u Mattila, 1980, Flunitrazepam: a review of its pharmacological properties and therapeutic use, Drugs, 20, 353, 10.2165/00003495-198020050-00002 Moon, 2013, An image analysis algorithm for malaria parasite stage classification and viability quantification, PloS One, 8, e61812, 10.1371/journal.pone.0061812 Nallan, 2005, Protein farnesyltransferase inhibitors exhibit potent antimalarial activity, J. Med. Chem., 48, 3704, 10.1021/jm0491039 Ncokazi, 2005, A colorimetric high-throughput beta-hematin inhibition screening assay for use in the search for antimalarial compounds, Anal. Biochem., 338, 306, 10.1016/j.ab.2004.11.022 Neill, 1992, Pathology of fatal and resolving Plasmodium berghei cerebral malaria in mice, Parasitology, 105, 165, 10.1017/S0031182000074072 Pal, 2009, Giardia, Entamoeba, and Trichomonas enzymes activate metronidazole (nitroreductases) and inactivate metronidazole (nitroimidazole reductases), Antimicrob. Agents Chemother., 53, 458, 10.1128/AAC.00909-08 Peters, 1975, The chemotherapy of rodent malaria, XXII. The value of drug-resistant strains of P. berghei in screening for blood schizontocidal activity, Ann. Trop. Med. Parasitol., 69, 155, 10.1080/00034983.1975.11686997 Raether, 2003, Nitroheterocyclic drugs with broad spectrum activity, Parasitol. Res., 90, S19, 10.1007/s00436-002-0754-9 Ribaut, 2008, Concentration and purification by magnetic separation of the erythrocytic stages of all human Plasmodium species, Malar. J., 7, 45, 10.1186/1475-2875-7-45 Rieckmann, 2006, The chequered history of malaria control: are new and better tools the ultimate answer?, Ann. Trop. Med. Parasitol., 100, 647, 10.1179/136485906X112185 Rishton, 2008, Molecular diversity in the context of leadlikeness: compound properties that enable effective biochemical screening, Curr. Opin. Chem. Biol., 12, 340, 10.1016/j.cbpa.2008.02.008 Roberts, 2016, Spirocyclic chromanes exhibit antiplasmodial activities and inhibit all intraerythrocytic life cycle stages, Int. J. Parasitol. Drugs Drug Resist, 6, 85, 10.1016/j.ijpddr.2016.02.004 Saenz, 2012, Novel 4-aminoquinoline analogs highly active against the blood and sexual stages of Plasmodium in vivo and in vitro, Antimicrob. Agents Chemother., 56, 4685, 10.1128/AAC.01061-12 Sandlin, 2011, Use of the NP-40 detergent-mediated assay in discovery of inhibitors of beta-hematin crystallization, Antimicrob. Agents Chemother., 55, 3363, 10.1128/AAC.00121-11 Sanni, 2002, Mouse models for erythrocytic-stage malaria, Methods Mol. Med., 72, 57 Singh, 2009, Chemoinformatic analysis of drugs, natural products, molecular libraries small molecule repository and combinatorial libraries, J. Chem. Inf. Model., 49, 1010, 10.1021/ci800426u Sinha, 2014, Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain, Bioorg. Med. Chem., 22, 3573, 10.1016/j.bmc.2014.05.024 Smilkstein, 2004, Simple and inexpensive fluorescence-based technique for high-throughput antimalarial drug screening, Antimicrob. Agents Chemother., 48, 1803, 10.1128/AAC.48.5.1803-1806.2004 Sorkin, 1985, Nifedipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy, in ischaemic heart disease, hypertension and related cardiovascular disorders, Drugs, 30, 182, 10.2165/00003495-198530030-00002 Srivastava, 1997, Atovaquone, a broad spectrum antiparasitic drug, collapses mitochondrial membrane potential in a malarial parasite, J. Biol. Chem., 272, 3961, 10.1074/jbc.272.7.3961 Thomas, 2010, Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1,2,3-triazole moiety, Eur. J. Med. Chem., 45, 3803, 10.1016/j.ejmech.2010.05.030 Trager, 1976, Human malaria parasites in continuous culture, Science, 193, 673, 10.1126/science.781840 Truong, 2009, Tolcapone: review of its pharmacology and use as adjunctive therapy in patients with Parkinson's disease, Clin. Interv. Aging, 4, 109, 10.2147/CIA.S3787 Tukulula, 2013, Synthesis and in vitro and in vivo pharmacological evaluation of new 4-aminoquinoline-based compounds, ACS Med. Chem. Lett., 4, 1198, 10.1021/ml400311r Vasilevich, 2012, Lessons from natural products chemistry can offer novel approaches for synthetic chemistry in drug discovery, J. Med. Chem., 55, 7003, 10.1021/jm300344v Walsh, 2011, Bioactivation of drugs: risk and drug design, Annu. Rev. Pharmacol. Toxicol., 51, 145, 10.1146/annurev-pharmtox-010510-100514 Wilkinson, 2011, Trypanocidal activity of nitroaromatic prodrugs: current treatments and future perspectives, Curr. Top. Med. Chem., 11, 2072, 10.2174/156802611796575894 Wilson, 2013, Defining the timing of action of antimalarial drugs against Plasmodium falciparum, Antimicrob. Agents Chemother., 57, 1455, 10.1128/AAC.01881-12 World Health Organization, 2016 Yan, 2011, A catalyst-free benzylic C-H bond olefination of azaarenes for direct Mannich-like reactions, J. Org. Chem., 76, 6849, 10.1021/jo2008934