Hybrid imidazole (benzimidazole)/pyridine (quinoline) derivatives and evaluation of their anticancer and antimycobacterial activity

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 31, Issue , 2016, Pages 96-103

  Mantu, Dorina ^a   Antoci, Vasilichia ^a   Moldoveanu, Costel ^a   Zbancioc, Gheorghita ^a   Mangalagiu, Ionel I ^a  

^a ALEXANDRU IOAN CUZA UNIVERSITY OF IASI   (Romania)

Author keywords

Anticancer; antimycobacterial; hybrid imidazole (benzimidazole) pyridine (quinoline); synthesis

Indexed keywords

2 (1H BENZO[D]IMIDAZOL 1 YL) N (PYRIDIN 2 YL)ACETAMIDE; 2 (1H BENZO[D]IMIDAZOL 1 YL) N (QUINOLIN 8 YL)ACETAMIDE; 2 (1H IMIDAZOL 1 YL) N (PYRIDIN 2 YL)ACETAMIDE; 2 (1H IMIDAZOL 1 YL) N (QUINOLIN 8 YL)ACETAMIDE; 2 CHLORO N (PYRIDIN 2 YL)ACETAMIDE; 2 CHLORO N (QUINOLIN 8 YL)ACETAMIDE; 3 (2 AMINO 2 OXOETHYL) 1 [2 OXO 2 (PYRIDIN 2 YLAMINO)ETHYL] 1H BENZO[D]IMIDAZOL 3 IUM IODIDE; 3 (2 AMINO 2 OXOETHYL) 1 [2 OXO 2 (QUINOLIN 8 YLAMINO)ETHYL] 1H BENZO[D]IMIDAZOL 3 IUM IODIDE; 3 (2 AMINO 2 OXOETHYL) 1 [2 OXO 2 (QUINOLIN 8 YLAMINO)ETHYL] 1H IMIDAZOL 3 IUM IODIDE; 3 (2 AMINO2 OXOETHYL) 1 [2 OXO 2 (PYRIDIN 2 YLAMINO)ETHYL] 1H IMIDAZOL 3 IUM IODIDE; 3 (2 ETHOXY 2 OXOETHYL) 1 [2 OXO 2 (PYRIDIN 2 YLAMINO)ETHYL] 1H BENZO[D]IMIDAZOL 3 IUM BROMIDE; 3 (2 ETHOXY 2 OXOETHYL) 1 [2 OXO 2 (PYRIDIN 2 YLAMINO)ETHYL] 1H IMIDAZOL 3 IUM BROMIDE; 3 (2 ETHOXY 2 OXOETHYL) 1 [2 OXO 2 (QUINOLIN 8 YLAMINO)ETHYL] 1H BENZO[D]IMIDAZOL 3 IUM BROMIDE; 3 (2 ETHOXY 2 OXOETHYL) 1 [2 OXO 2 (QUINOLIN 8 YLAMINO)ETHYL] 1H IMIDAZOL 3 IUM BROMIDE; 3 ALLYL 1 [2 OXO 2 (PYRIDIN 2 YLAMINO)ETHYL] 1H BENZO[D]IMIDAZOL 3 IUM BROMIDE; 3 ALLYL 1 [2 OXO 2 (PYRIDIN 2 YLAMINO)ETHYL] 1H IMIDAZOL 3 IUM BROMIDE; 3 ALLYL 1 [2 OXO 2 (QUINOLIN 8 YLAMINO)ETHYL] 1H BENZO[D]IMIDAZOL 3 IUM BROMIDE; 3 ALLYL 1 [2 OXO 2 (QUINOLIN 8 YLAMINO)ETHYL] 1H IMIDAZOL 3 IUM BROMIDE; ANTIMYCOBACTERIAL AGENT; ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; HALOPERIDOL; IMIDAZOLE DERIVATIVE; METOPROLOL TARTRATE; PHENYTOIN; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; RIFAMPICIN; SIMVASTATIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTIINFECTIVE AGENT; BENZIMIDAZOLE; QUINOLINE;

ACYLATION; ALKYLATION; ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL GROWTH; CANCER INHIBITION; CELL PROLIFERATION; COMPARATIVE STUDY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DESIGN; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; IC50; IC90; IN VITRO STUDY; MDA-MB CELL LINE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; RENAL CANCER CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; MICROBIAL SENSITIVITY TEST; MYCOBACTERIUM TUBERCULOSIS; SOLUBILITY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; QUINOLINES; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84973100665     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756366.2016.1190711     Document Type: Article

References (34)

1. Pozharskii AF, Soldatenkov AT, Katritzky AR. Heterocycles in life and society:an introduction to heterocyclic chemistry, biochemistry and applications. 2nd ed. Chichester:John Wiley & Sons; 2011
2. Grahman PL. An introduction to medicinal chemistry. 2nd ed. Oxford:Oxford University Press; 2001
3. Silverman RB, The organic chemistry of drug design and drug action. London:Academic Press; 1992
4. a. World Health Organization Tuberculosis Programme. Available from:Global tuberculosis report 2015/WHO/ http://www.who.int/tb/publications/global_report/en/ [last accessed 19 Feb 2016]. b. http://www.who.int/mediacentre/factsheets/fs297/en/ [last accessed 19 Feb 2016]
5. Rescifina A, Zagni C, Varrica MG, et al. Recent advances in small organic molecules as DNA intercalating agents:synthesis, activity, and modeling. Eur J Med Chem 2014;74:95–115
6. Xiang P, Zhou T, Wang L, et al. Novel benzothiazole, benzimidazolee and benzoxazole derivatives as potential antitumor agents:synthesis and preliminary in vitro biological evaluation. Molecules 2012;17:873–83
7. Wissner A, Mansour TS. The development of HKI-272 and related compounds for the treatment of cancer. Arch Pharm 2008;341:465–77
8. Denny WA. DNA minor groove alkylating agents. Curr Med Chem 2001;8:533–44
9. Zbancioc AM, Zbancioc G, Tanase C, et al. Design, synthesis and in vitro anticancer activity of a new class of bifunctional DNA intercalators. Lett Drug Des Discov 2010;7:644–9
10. Luca MC, Tura V, Mangalagiu II. Considerations concerning design and mechanism of action of a new class of anticancer dual DNA intercalators. Med Hypotheses 2010;75:627–9
11. Koseki Y, Kinjo T, Kobayashi M, Aoki S. Identification of novel antimycobacterial chemical agents through the in silico multi-conformational structure-based drug screening of a large-scale chemical library. Eur J Med Chem 2013;60:333–9
12. Gising J, Nilsson MT, Odell LR, et al. Trisubstituted imidazoles as Mycobacterium tuberculosis glutamine synthetase inhibitors. J Med Chem 2012;55:2894–8
13. Villemagne B, Crauste C, Flipo M, et al. Tuberculosis:the drug development pipeline at a glance. Eur J Med Chem 2012;51:1–16
14. Pandey J, Tiwari VK, Verma SS, et al. Synthesis and antitubercular screening of imidazole derivatives. Eur J Med Chem 2009;44:3350–5
15. Danac R, Managalagiu II. Antimycobacterial activity of nitrogen heterocycles derivatives:bipyridine derivatives. Part III. Eur J Med Chem 2014;74:664–70
16. Danac R, Al Matarneh C, Shova S, et al. New indolizines with phenanthroline skeleton:synthesis, structure, antimycobacterial and anticancer properties. Bioorgan Med Chem 2015;23:2318–27
17. Al Matarneh C, Mangalagiu II, Shova S, Danac R. Synthesis, structure, antimycobacterial and anticancer evaluation of new pyrrolo-phenanthroline derivatives. J Enzym Inh Med Chem 2015;31:470–80
18. Antoci V, Mantu D, Cozma DG, et al. Hybrid anticancer 1,2-diazine derivatives with multiple mechanism of action. Part 3. Med Hypotheses 2014;82:11–15
19. Balan AM, Miron A, Tuchilus C, et al. Synthesis and in vitro analysis of novel dihydroxyacetophenone derivatives with antimicrobial and antitumor activities. Med Chem 2014;10:476–83
20. Danac R, Daniloaia T, Antoci V, Mangalagiu II. Design, synthesis and antimycobacterial activity of some new azaheterocycles:phenanthroline with p-halogeno-benzoyl skeleton. Part V. Lett Drug Des Discov 2015;12:14–19
21. Mantu D, Antoci V, Mangalagiu II. Design, synthesis and antimycobacterial activity of some new pyridazine derivatives:bis-pyridazine. Part IV. Infect Disord Drug Targets 2013;13:344–51
22. Mantu D, Luca C, Moldoveanu C, et al. Synthesis and antituberculosis activity of some new pyridazine derivatives. Part II. Eur J Med Chem 2010;45:5164–8
23. Moldoveanu C, Mangalagiu G, Drochioiu G, et al. New antituberculosis compounds derived from diazine. An Stiint Univ “Al.I.Cuza” Iasi 2003;11:367–74. [Chem. Abstr. 142 (2004) 56249]
24. Ma L, Li S, Zheng H, et al. Synthesis and biological activity of novel barbituric and thiobarbituric acid derivatives against non-alcoholic fatty liver disease. Eur J Med Chem 2011;46:2003–10
25. Zhou X, Yan W, Zhao T, et al. Rhodamine based derivative and its zinc complex:synthesis and recognition behavior toward Hg(II). Tetrahedron 2013;69:9535–9
26. US National Cancer Institute (NCI). 2016. Bethesda. Available from:http://dtp.nci.nih.gov/ [last accessed 19 Feb 2016]
27. Shoemaker RH. The NCI60 human tumour cell line anticancer drug screen. Nat Rev Cancer 2006;6:813–23
28. Monks A, Scudiero D, Skehan P, et al. Feasibility of a high-flux anticancer drug screen utilizing a diverse panel of human tumour cell lines in culture. J Natl Cancer Inst 1991;83:757–66
29. Boyd RM, Paull KD. Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen. Drug Develop Res 1995;34:91–109
30. Bevan CD, Lloyd RS. A high-throughput screening method for the determination of aqueous drug solubility using laser nephelometry in microtiter plates. Anal Chem 2000;72:1781–7
31. Carroll P, Schreuder LJ, Muwanguzi-Karugaba J, et al. Sensitive detection of gene expression in Mycobacteria under replicating and non-replicating conditions using optimized far-red reporters. PLoS One 2010;5:e9823
32. Ollinger J, Bailey MA, Moraski GC, et al. A dual read-out assay to evaluate the potency of compounds active against Mycobacterium tuberculosis. PLoS One 2013;8:e60531
33. Zelmer A, Carroll P, Andreu N, et al. A new in vivo model to test anti-tuberculosis drugs using fluorescence imaging. J Antimicrob Chemother 2012;67:1948–60
34. Lambert RJ, Pearson J. Susceptibility testing:accurate and reproducible minimum inhibitory concentration (MIC) and non-inhibitory concentration (NIC) values. J Appl Microbiol 2000;88:784–90