Incorporation of Fluorinated Pyridine in the Side Chain of 4-Aminoquinolines: Synthesis, Characterization and Antibacterial Activity

Reza Ranjbar-Karimi; Alireza Poorfreidoni

doi:10.1055/s-0043-116674

Drug Research, Table of Contents

Drug Res (Stuttg) 2018; 68(01): 17-22
DOI: 10.1055/s-0043-116674

Original Article

Incorporation of Fluorinated Pyridine in the Side Chain of 4-Aminoquinolines: Synthesis, Characterization and Antibacterial Activity

Reza Ranjbar-Karimi

¹Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan, Islamic Republic of Iran

,

Alireza Poorfreidoni

¹Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan, Islamic Republic of Iran

› Author Affiliations

Abstract

A series of hybrid of 4-aminoquinoline and fluorinated pyridine derivatives were synthesized and their chemical structure were confirmed by ¹⁹F-NMR, ¹H-NMR, ¹³C-NMR and FT-IR. All compounds were tested against one Gram-positive and one Gram-negative bacteria to assess their in vitro antibacterial activity. Compounds 10a, 10b, 11a and 12b showed moderate antibacterial activity against Gram-positive bacterium, Staphylococcus aureus.

Key words

hydroxy- and amine-functionalized quinoline - pentafluoropyridine - 2,3,5,6-Tetrafluoro-4-phenylsulphonyl pyridine - synthesis - antibacterial activity

Full Text

References

References
1 Michael JP. Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 2008; 25: 166-187
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; 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
6 Kaminsky D, Meltzer RI. Quinoline antibacterial agents. Oxolinic acid and related compounds. J Med Chem 1968; 11: 160-163
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
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
9 Musiol R, Jampilek J, Buchta V. et al. Antifungal properties of new series of quinoline derivatives. Bioorg Med Chem 2006; 14: 3592-3598
10 Coatney GR. Pitfalls in a discovery: The chronicle of chloroquine. Am J Trop Med Hyg 1963; 12: 121-128
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
12 Woodrow CJ, Haynes RK, Krishna S. Artemisinins. Postgrad Med J 2005; 81: 71-78
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 Chem Int Ed 2003; 42: 5274-5293
15 Ridley RG. Medical need, scientific opportunity and the drive for 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
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
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
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
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
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
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
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
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
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
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
29 Halpern DF, Vernice GG. Chemistry of organic fluorine compounds II. Washington, DC: American Chemical Society; 1995: 172
30 Ojima I, Kobayashi Y, Yagulpolskii YL. Fluorine in medicinal chemistry and chemical biology. United Kingdom: John Wiley & Sons Ltd; 2009: 291-312
31 Chambers RD. Fluorine in organic chemistry. Blackwell: Oxford; 2004
32 Banks RE, Smart BE, Tatlow JC. Organofluorine chemistry. Principles and commercial applications. New York: Plenum; 1994
33 Chambers RD, Sargent CR. Polyfluoroheteroaromatic compounds. Adv Heterocycl Chem 1981; 28: 1-71
34 Brooke GM. The preparation and properties of polyfluoro aromatic and 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
36 Banks RE, Burgess JE, Cheng WM. et al. Heterocyclic polyfluoro-compounds. Part IV. Nucleophilic substitution in pentafluoropyridine: the preparation and properties of some 4-substituted 2,3,5,6-tetrafluoropyridines. J Chem Soc 1965; 575-581
37 Sandford G, Slater R, Yufit DS. et al. Tetrahydropyrido[3,4-b]pyrazine scaffolds from pentafluoropyridine. J Org Chem 2005; 70: 7208-7216
38 Ranjbar-Karimi R, Hashemi-Uderji S, Danesteh R. Synthesis of some di- and trifluoro quinoxaline and dioxine derivatives from pentafluoropyridine. J Iran Chem Soc 2012; 9: 747-755
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
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
41 Pretorius SI, Breytenbach WJ, de Kock C. et al. Synthesis, characterization and antimalarial activity of quinoline–pyrimidine hybrids. Bioorgan Med Chem 2013; 21: 269-277
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: 340-315

Supplementary Material

Supporting Information