Synthesis, antiproliferative and anti-dengue virus evaluations of 2-aroyl-3-arylquinoline derivatives

European Journal of Medicinal Chemistry

Volumn 79, Issue , 2014, Pages 66-76

  Tseng, Chih Hua ^a   Lin, Chun Kuang ^b   Chen, Yeh Long ^a   Hsu, Chih Yao ^a   Wu, Huey Nan ^c   Tseng, Chin Kai ^d   Lee, Jin Ching ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

^c INSTITUTE OF MOLECULAR BIOLOGY   (Taiwan)

^d NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

2 Aroyl 3 arylquinoline; Anti dengue virus; Antiproliferative; Ribavirin; Topotecan

Indexed keywords

(4 FLUOROPHENYL) 2 METHYLQUINOLINE 4 CARBOXYLIC ACID; 2 (4 HYDROXYBENZOYL) 3 (4 HYDROXYPHENYL)QUINOLINE; 2 (HYDROXY 3,4,5 TRIMETHOXYPHENYLMETHYL) 3 (4 METHOXYPHENYL)QUINOLINE; 2 (HYDROXY 4 METHOXYPHENYLMETHYL) 3 (4 METHOXYPHENYL) QUINOLINE; 2 (HYDROXYPHENYLMETHYL) 3 (4 METHOXYPHENYL) 6 METHOXYQUINOLINE; 2 (HYDROXYPHENYLMETHYL) 3 (4 METHOXYPHENYL)QUINOLINE; 2 BENZOYL 3 (4 FLUOROPHENYL)QUINOLINE; 2 BENZOYL 3 (4 METHOXYPHENYL)QUINOLINE; 2 BENZOYL 6 FLUORO 3 (4 FLUOROPHENYL)QUINOLINE; 2 BENZOYL 6 FLUORO 3 (4 METHOXYPHENYL)QUINOLINE; 2 BENZOYL 6 METHOXY 3 (4 METHOXYPHENYL)QUINOLINE; 3 (4 FLUOROPHENYL) 2 (HYDROXYPHENYLMETHYL)QUINOLINE; 3 (4 FLUOROPHENYL) 2 METHYLQUINOLINE; 3 (4 FLUOROPHENYL) 6 FLUOROQUINOLINE 2 CARBALDEHYDE; 3 (4 FLUOROPHENYL)QUINOLINE 2 CARBALDEHYDE; 6 FLUORO 2 (HYDROXYPHENYLMETHYL) 3 (4 FLUOROPHENYL) QUINOLINE; 6 FLUORO 2 (HYDROXYPHENYLMETHYL) 3 (4 METHOXYPHENYL) QUINOLINE; 6 FLUORO 3 (4 FLUOROPHENYL) 2 METHYLQUINOLINE; 6 FLUORO 3 (4 FLUOROPHENYL) 2 METHYLQUINOLINE 4 CARBOXYLIC ACID; 6 FLUORO 3 (4 METHOXYPHENYL) 2 METHYLQUINOLINE; 6 FLUORO 3 (4 METHOXYPHENYL) 2 METHYLQUINOLINE 4 CARBOXYLIC ACID; 6 FLUORO 3 (4 METHOXYPHENYL)QUINOLINE 2 CARBALDEHYDE; 6 METHOXY 3 (4 METHOXYPHENYL) 2 METHYLQUINOLINE; 6 METHOXY 3 (4 METHOXYPHENYL) 2 METHYLQUINOLINE 4 CARBOXYLIC ACID; 6 METHOXY 3 (4 METHOXYPHENYL)QUINOLINE 2 CARBALDEHYDE; ANTIVIRUS AGENT; QUINOLINE DERIVATIVE; RIBAVIRIN; TOPOTECAN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; DENGUE VIRUS 2; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; HYDROGEN BOND; IC 50; NONHUMAN; OXIDATION; PROTEIN EXPRESSION; VIRUS REPLICATION; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DENGUE VIRUS; DOSE RESPONSE; DRUG EFFECTS; HUMAN; MCF 7 CELL LINE; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TOXICITY; TUMOR CELL LINE;

ANTIVIRAL AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DENGUE VIRUS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MCF-7 CELLS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84898492804     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.074     Document Type: Article

References (31)

1. J.G. Rigau-Pérez, G.G. Clark, D.J. Gubler, P. Reiter, E.J. Sanders, and A.V. Vorndam Dengue and dengue haemorrhagic fever Lancet 352 1998 971 977 (Pubitemid 28427290)
2. J.L. Deen, E. Harris, B. Wills, A. Balmaseda, S.N. Hammond, C. Rocha, N.M. Dung, N.T. Hung, T.T. Hien, and J.J. Farrar The WHO dengue classification and case definitions: time for a reassessment Lancet 368 2006 170 173 (Pubitemid 43994174)
3. D.J. Gubler Epidemic dengue/dengue hemorrhagic fever as a public health, social and economic problem in the 21st century Trends in Microbiology 10 2002 100 103 (Pubitemid 34119347)
4. D.J. Gubler, and G.G. Clark Dengue/dengue hemorrhagic fever: the emergence of a global health problem Emerging Infectious Diseases 1 1995 55 57
5. P. Leyssen, E. De Clercq, and J. Neyts Molecular strategies to inhibit the replication of RNA viruses Antiviral Research 78 2008 9 25
6. C.G. Noble, Y.L. Chen, H. Dong, F. Gu, S.P. Lim, W. Schul, Q.Y. Wang, and P.Y. Shi Strategies for development of dengue virus inhibitors Antiviral Research 85 2010 450 462
7. T.J. Chambers, C.S. Hahn, R. Galler, and C.M. Rice Flavivirus genome organization, expression, and replication Annual Review of Microbiology 44 1990 649 688
8. S. Mukhopadhyay, R.J. Kuhn, and M.G. Rossmann A structural perspective of the Flavivirus life cycle Nature Reviews Microbiology 3 2005 13 22 (Pubitemid 40028466)
9. J.M. Mackenzie, A.A. Khromykh, M.K. Jones, and E.G. Westaway Subcellular localization and some biochemical properties of the Flavivirus Kunjin nonstructural proteins NS2A and NS4A Virology 245 1998 203 215 (Pubitemid 28394183)
10. Q.Y. Wang, S.J. Patel, E. Vangrevelinghe, H.Y. Xu, R. Rao, D. Jaber, W. Schul, F. Gu, O. Heudi, N.L. Ma, M.K. Poh, W.Y. Phong, T.H. Keller, E. Jacoby, and S.G. Vasudevan A small-molecule dengue virus entry inhibitor Antimicrobial Agents and Chemotherapy 53 2009 1823 1831
11. P. Niyomrattanakit, Y.L. Chen, H. Dong, Z. Yin, M. Qing, J.F. Glickman, K. Lin, D. Mueller, H. Voshol, J.Y. Lim, S. Nilar, T.H. Keller, and P.Y. Shi Inhibition of dengue virus polymerase by blocking of the RNA tunnel Journal of Virology 84 2010 5678 5686
12. R.S. Upadhayaya, J.K. Vandavasi, R.A. Kardile, S.V. Lahore, S.S. Dixit, H.S. Deokar, P.D. Shinde, M.P. Sarmah, and J. Chattopadhyaya Novel quinoline and naphthalene derivatives as potent antimycobacterial agents European Journal of Medicinal Chemistry 45 2010 1854 1867
13. S. Eswaran, A.V. Adhikari, and R.A. Kumar New 1,3-oxazolo[4,5-c]quinoline derivatives: synthesis and evaluation of antibacterial and antituberculosis properties European Journal of Medicinal Chemistry 45 2010 957 966
14. S. Eswaran, A.V. Adhikari, N.K. Pal, and I.H. Chowdhury Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents Bioorganic & Medicinal Chemistry Letters 20 2010 1040 1044
15. S. Eswaran, A.V. Adhikari, and N.S. Shetty Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety European Journal of Medicinal Chemistry 44 2009 4637 4647
16. C.L. Yang, C.H. Tseng, Y.L. Chen, C.M. Lu, C.L. Kao, H.Y. Tseng, M.H. Wu, and C.C. Tzeng Identification of benzofuro[2,3-b]quinoline derivatives as a new class of antituberculosis agents European Journal of Medicinal Chemistry 45 2010 602 607
17. C.H. Tseng, C.C. Tzeng, C.L. Yang, P.J. Lu, H.L. Chen, H.Y. Li, Y.C. Chuang, C.N. Yang, and Y.L. Chen Synthesis and antiproliferative evaluation of certain indeno[1,2-c]quinoline derivatives. Part 2 Journal of Medicinal Chemistry 53 2010 6164 6179
18. Y.W. Chen, Y.L. Chen, C.H. Tseng, C.C. Liang, C.N. Yang, Y.C. Yao, P.J. Lu, and C.C. Tzeng Discovery of 4-anilinofuro[2,3-b]quinoline derivatives as selective and orally active compounds against non-small-cell lung cancers Journal of Medicinal Chemistry 54 2011 4446 4461
19. C.H. Tseng, Y.L. Chen, C.L. Yang, C.M. Cheng, C.H. Han, and C.C. Tzeng Synthesis of 6-substituted 9-methoxy-11H-indeno[1,2-c]quinoline-11-one derivatives as potential anticancer agents Bioorganic & Medicinal Chemistry 20 2012 4397 4404
20. F.S. Chang, W.C. Chen, C.H. Wang, C.C. Tzeng, and Y.L. Chen Synthesis and antiproliferative evaluations of certain 2-phenylvinylquinoline (2-styrylquinoline) and 2-furanylvinylquinoline derivatives Bioorganic & Medicinal Chemistry 18 2010 124 133
21. C.H. Tseng, Y.L. Chen, K.Y. Chung, C.H. Wang, S.I. Peng, C.M. Cheng, and C.C. Tzeng Synthesis and antiproliferative evaluation of 2,3-diarylquinoline derivatives Organic & Biomolecular Chemistry 9 2011 3205 3216
22. C.H. Tseng, Y.L. Chen, C.Y. Hsu, T.C. Chen, C.M. Cheng, H.C. Tso, Y.J. Lu, and C.C. Tzeng Synthesis and antiproliferative evaluation of 3-phenylquinolinylchalcone derivatives against non-small cell lung cancers and breast cancers European Journal of Medicinal Chemistry 59 2013 274 282
23. E.J. Koh, M.I. EI-Gamal, C.H. Oh, S.H. Lee, T. Sim, G. Kim, H.S. Choi, J.H. Hong, S. Lee, and K.H. Yoo New diarylamides and diarylureas possessing 8-amino(acetamido)quinoline scaffold: synthesis, antiproliferative activities against melanoma cell lines, kinase inhibition, and in silico studies European Journal of Medicinal Chemistry 70 2013 10 21
24. R.K. Arafa, G.H. Hegazy, G.A. Piazza, and A.H. Abadi Synthesis and in vitro antiproliferative effect of novel quinoline-based potential anticancer agents European Journal of Medicinal Chemistry 63 2013 826 832
25. N. Ahmed, K.G. Brahmbhatt, S. Sabde, D. Mitra, I.P. Singh, and K.K. Bhutani Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols Bioorganic & Medicinal Chemistry 18 2010 2872 2879
26. H.K. Peng, C.K. Lin, S.Y. Yang, C.K. Tseng, C.C. Tzeng, J.C. Lee, and S.C. Yang Synthesis and anti-HCV activity evaluation of anilinoquinoline derivatives Bioorganic & Medicinal Chemistry Letters 22 2012 1107 1110
27. T. Parkinson, and D.C. Pryde Small molecule drug discovery for dengue and West Nile viruses: applying experience from hepatitis C virus Future Medicinal Chemistry 2 2010 1181 1203
28. M.H. Palmer, and P.S. McIntyre The Pfitzinger reaction with unsymmetrical ketones Journal of the Chemical Society B 5 1969 539 543
29. P.K. Russell, and A. Nisalak Dengue virus identification by the plaque reduction neutralization test Journal of Immunology 99 1967 291 296
30. N.W. Roehm, G.H. Rodgers, S.M. Hatfield, and A.L. Glasebrook An improved colorimetric assay for cell proliferation and viability utilizing the tetrazolium salt XTT Journal of Immunological Methods 142 1991 257 265
31. J.C. Lee, C.K. Tseng, K.J. Chen, K.J. Huang, C.K. Lin, and Y.T. Lin A cell-based reporter assay for inhibitor screening of hepatitis C virus RNA-dependent RNA polymerase Analytical Biochemistry 403 2010 52 62