Thieme
Original Article
Acknowledgement
The authors wish to thank Vali-e-Asr University of Rafsanjan for par-
[20] De D, Krogstad FM, Cogswell FB et al. Aminoquinolines that
circumvent resistance in Plasmodium falciparum in vitro. J. Am J Trop
Med Hyg 1996; 55: 579–583
tially funding this work.
[21] Egan TJ. Haemozoin (malaria pigment): A unique crystalline drug
target. Targets 2003; 2: 115–124
[22] Stocks PA, Raynes KJ, Bray PC et al. Novel short chain chloroquine
analogues retain activity against chloroquine resistant K1 plasmodium
falciparum. J Med Chem 2002; 45: 4975–4983
Conflict of Interest
The authors declare that there is no conflict of interest.
[23] Martirosyan AR, Rahim-Bata R, Freeman AB et al. Differentiation-inducing
quinolines as experimental breast cancer agents in the MCF-7 human
breast cancer cell model. Biochem. Pharmacol. 2004; 68: 1729–1738
References
[24] Ferrer R, Lobo G, Gamboa N et al. Synthesis of [(7-chloroquinolin-4-yl)
amino]chalcones: Potential antimalarial and anticancer agents. Sci
Pharm 2009; 77: 725–741
[1] Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep
2008; 25: 166–187
[25] Al-Dosari MS, Ghorab MM, Al-Said MS et al. Discovering some novel
7-chloroquinolines carrying a biologically active benzenesulfonamide
moiety as a new Class of anticancer agents. Chem Pharm Bull 2013;
61: 50–58
[2] Grundo MF. Quinoline, quinazoline, and acridone alkaloids. Nat Prod
Rep 1990; 7: 131–138
[3] Montalban AG. Heterocycles in natural product synthesis. John wiley;
[26] Feng TS, Guantai EM, Nell MJ et al. Antiplasmodial and antitumor
activity of dihydroartemisinin analogs derived via the aza-Michael
addition reaction. Bioorg Med Chem Lett 2001; 21: 2882–2886
2011: 299–337
[4] Rahman A. Studies in natural products chemistry. Elsevier; 2003: 28
[5] Nakamura T, Oka M, Aizawa K et al. Direct interaction between a
quinoline derivative, MS-209, and multidrug resistance protein (MRP)
in human gastric cancer cells. Biochem Biophys Res Commun 1999;
255: 618–624
[27] De Souza MVN, Pais KC, Kaiser CR et al. Synthesis and in vitro
antitubercular activity of a series of quinoline derivatives. Bioorgan
Med Chem 2009; 17: 1474–1480
[28] Smart BE. Fluorine substituent effects (on bioactivity). J Fluorine Chem
2001; 109: 3–11
[6] Kaminsky D, Meltzer RI. Quinoline antibacterial agents. Oxolinic acid
and related compounds. J Med Chem 1968; 11: 160–163
[29] Halpern DF, Vernice GG. Chemistry of organic fluorine compounds II.
Washington, DC: American Chemical Society; 1995: 172
[7] Font M, Monge A, Ruiz I et al. Structure-activity relationships in
quinoline Reissert derivatives with HIV-1 reverse transcriptase
inhibitory activity. Drug Des Discovery 1997; 14: 259–272
[30] Ojima I, Kobayashi Y, Yagulpolskii YL. Fluorine in medicinal chemistry
and chemical biology. United Kingdom: John Wiley & Sons Ltd; 2009:
291–312
[8] Sloboda AE, Powell D, Poletto JF et al. Antiinflammatory and
antiarthritic properties of a substituted quinoline carboxylic acid: CL
306,293. J Rheumatol 1991; 18: 855–860
[31] Chambers RD. Fluorine in organic chemistry. Blackwell: Oxford; 2004
[32] Banks RE, Smart BE, Tatlow JC. Organofluorine chemistry. Principles
[9] Musiol R, Jampilek J, Buchta V et al. Antifungal properties of new series
of quinoline derivatives. Bioorg Med Chem 2006; 14: 3592–3598
and commercial applications. New York: Plenum; 1994
[33] Chambers RD, Sargent CR. Polyfluoroheteroaromatic compounds. Adv
[10] Coatney GR. Pitfalls in a discovery: The chronicle of chloroquine. Am J
Heterocycl Chem 1981; 28: 1–71
Trop Med Hyg 1963; 12: 121–128
[34] Brooke GM. The preparation and properties of polyfluoro aromatic and
[11] Haynes RK. From artemisinin to new artemisinin antimalarials:
biosynthesis, extraction, old and new derivatives, stereochemistry and
medicinal chemistry requirements. Curr Top Med Chem 2006; 6:
509–537
heteroaromatic compounds. J Fluorine Chem 1997; 86: 1–76
[35] Chambers RD, Hutchinson J, Musgrave WKR. Polyfluoro-heterocyclic
compounds. Part II. Nucleophilic substitution in pentafluoropyridine.
J Chem Soc 1964; 3736–3739
[12] Woodrow CJ, Haynes RK, Krishna S. Artemisinins. Postgrad Med J 2005;
81: 71–78
[36] Banks RE, Burgess JE, Cheng WM et al. Heterocyclic polyfluoro-com-
pounds. Part IV. Nucleophilic substitution in pentafluoropyridine: the
preparation and properties of some 4-substituted 2,3,5,6-tetrafluoro-
pyridines. J Chem Soc 1965; 575–581
[13] Gelb MH. Drug discovery for malaria: A very challenging and timely
endeavor. Curr Opin Chem Biol 2007; 11: 440–445
[14] Wiesner J, Ortmann R, Jomaa H et al. New antimalarial drugs. Angew
[37] Sandford G, Slater R, Yufit DS et al. Tetrahydropyrido[3,4-b]pyrazine
Chem Int Ed 2003; 42: 5274–5293
scaffolds from pentafluoropyridine. J Org Chem 2005; 70: 7208–7216
[15] Ridley RG. Medical need, scientific opportunity and the drive for
[38] Ranjbar-Karimi R, Hashemi-Uderji S, Danesteh R. Synthesis of some
di- and trifluoro quinoxaline and dioxine derivatives from pentafluoro-
pyridine. J Iran Chem Soc 2012; 9: 747–755
antimalarial drugs. Nature 2002; 415: 686–693
[16] Kaur K, Jain M, Reddy RP et al. Quinolines and structurally related
heterocycles as antimalarials. Eur J Med Chem 2010; 45: 3245–3264
[39] Baron A, Sandford G, Slater R et al. Polyfunctional
tetrahydropyrido[2,3-b]pyrazine scaffolds from 4-phenylsulfonyl
tetrafluoropyridine. J Org Chem 2005; 70: 9377–9381
[17] Dola VR, Soni A, Agarwal P et al. Synthesis and evaluation of chirally
defined side chain variants of 7-chloro-4-aminoquinoline to overcome
drug resistance in malaria chemotherapy. Antimicrob Agents
Chemother 2017; 61: e01152–16
[40] Ranjbar-Karimi R, Mousavi M. Regiochemistry of nucleophilic
substitution of 4-phenylsulfonyl tetrafluoropyridine with unequal
bidentate nucleophiles. J Fluorine Chem 2010; 131: 587–591
[18] Saenz FE, Mutka T, Udenze K et al. Novel 4-aminoquinoline analogs
highly active against the blood and sexual stages of Plasmodium in
vivo and in vitro. Antimicrob Agents Chemother 2012; 56: 4685–4692
[41] Pretorius SI, Breytenbach WJ, de Kock C et al. Synthesis, characteriza-
tion and antimalarial activity of quinoline–pyrimidine hybrids.
Bioorgan Med Chem 2013; 21: 269–277
[19] Thayer AM. New antimalarial drugs are needed to ensure that effective
and affordable treatments continue to be available and are not lost to
parasite resistance. Chem Eng News 2005; 83: 69–82
[42] Wang X, Xie X, Cai Y et al. Design, synthesis and antibacterial
evaluation of some new 2-phenyl-quinoline-4-carboxylic acid
derivatives. Molecules 2016; 21: 340–315Original Article
Ranjbar-Karimi R, Poorfreidoni Alireza. Incorporation of Fluorinated Pyridine … Drug Res