A new class of 2-(4-cyanophenyl amino)-4-(6-bromo-4-quinolinyloxy)-6- piperazinyl (piperidinyl)-1,3,5-triazine analogues with antimicrobial/ antimycobacterial activity

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 3, 2012, Pages 370-379

  Patel, Rahul V ^a   Kumari, Premlata ^a   Rajani, Dhanji P ^b   Chikhalia, Kishor H ^c  

^a SARDAR VALLABHBHAI NATIONAL INSTITUTE OF TECHNOLOGY   (India)

^b Microcare Laboratory   (India)

^c GUJARAT UNIVERSITY   (India)

Author keywords

2,4,6 trichloro 1,3,5 triazin; 6 bromo 4 hydroxyquinoline; Antimicrobial activity; Antimycobacterial activity; Piperazine

Indexed keywords

2 (4 CYANOPHENYL AMINO) 4 (6 BROMO 4 QUINOLINYLOXY) 6 PIPERAZINYL (PIPERIDINYL) 1,3,5 TRIAZINE; ANTIINFECTIVE AGENT; CIPROFLOXACIN; ETHAMBUTOL; ISONIAZID; KETOCONAZOLE; PYRAZINAMIDE; RIFAMPICIN; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

AGAR DILUTION; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; ASPERGILLUS; ASPERGILLUS CLAVATUS; ASPERGILLUS FUMIGATUS; ASPERGILLUS NIGER; BACILLUS CEREUS; BACTERIAL STRAIN; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DISK DIFFUSION; DRUG EFFICACY; DRUG SYNTHESIS; ESCHERICHIA COLI; FLUORINE NUCLEAR MAGNETIC RESONANCE; IN VITRO STUDY; INFRARED SPECTROSCOPY; KLEBSIELLA PNEUMONIAE; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; PROTEUS VULGARIS; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHI; SHIGELLA; SHIGELLA FLEXNERIA; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; DOSE-RESPONSE RELATIONSHIP, DRUG; FUNGI; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

ASPERGILLUS CLAVATUS; ASPERGILLUS FUMIGATUS; ASPERGILLUS NIGER; BACILLUS CEREUS; CANDIDA ALBICANS; ESCHERICHIA COLI; FUNGI; KLEBSIELLA PNEUMONIAE; MYCOBACTERIUM TUBERCULOSIS; PROTEUS VULGARIS; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHI; SHIGELLA; STAPHYLOCOCCUS AUREUS;

EID: 84860363364     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.592491     Document Type: Article

References (34)

1. Nathan C. Antibiotics at the crossroads. Nature 2004;431:899-902. (Pubitemid 39434399)
2. Raviglione MC. The TB epidemic from 1992 to 2002. Tuberculosis (Edinb) 2003;83:4-14.
3. NIAID. http://www3.niaid.nih.gov/topics/tuberculosis
4. TAACF. http://www.taacf.org/about-TB-background.htm.
5. World Health Organization, Global tuberculosis control: A short update to the 2009 report. http://www.who.int/tb/publications/ global-report/2009/update/ en/index.html.
6. Mahajan DH, Pannecouque C, De Clercq E, Chikhalia KH. Synthesis and studies of new 2-(coumarin-4-yloxy)-4,6-(substituted)-Striazine derivatives as potential anti-HIV agents. Arch Pharm (Weinheim) 2009;342:281-290.
7. Chikhalia KH, Patel MJ. Design, synthesis and evaluation of some 1,3,5-triazinyl urea and thiourea derivatives as antimicrobial agents. J Enzyme Inhib Med Chem 2009;24:960-966.
8. Patel DH, Chikhalia KH, Shah NK, Patel DP, Kaswala PB, Buha VM. Synthesis and antimicrobial studies of s-triazine based heterocycles. J Enzyme Inhib Med Chem 2010;25:121-125.
9. Zhou C, Min J, Liu Z, Young A, Deshazer H, Gao T et al. Synthesis and biological evaluation of novel 1,3,5-triazine derivatives as antimicrobial agents. Bioorg Med Chem Lett 2008;18:1308-1311. (Pubitemid 351226548)
10. Srinivas K, Srinivas U, Bhanuprakash K, Harakishore K, Murthy US, Rao VJ. Synthesis and antibacterial activity of various substituted s-triazines. Eur J Med Chem 2006;41:1240-1246. (Pubitemid 44666218)
11. Baliani A, Bueno GJ, Stewart ML, Yardley V, Brun R, Barrett MP, Gilbert IH. Synthesis and antibacterial activity of various substituted s-triazines. Eur J Med Chem 2006;41:1240-1246.
12. Menicagli R, Samaritani S, Signore G, Vaglini F, Dalla Via L. In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines: new molecules in anticancer research. J Med Chem 2004;47:4649-4652. (Pubitemid 39195555)
13. Garaj V, Puccetti L, Fasolis G, Winum JY, Montero JL, Scozzafava A et al. Carbonic anhydrase inhibitors: novel sulfonamides incorporating 1,3,5-triazine moieties as inhibitors of the cytosolic and tumour-associated carbonic anhydrase isozymes I, II and IX. Bioorg Med Chem Lett 2005;15:3102-3108. (Pubitemid 40755204)
14. Melato S, Prosperi D, Coghi P, Basilico N, Monti D. A combinatorial approach to 2,4,6-trisubstituted triazines with potent antimalarial activity: combining conventional synthesis and microwaveassistance. Chemmedchem 2008;3:873-876.
15. Xiong YZ, Chen FE, Balzarini J, De Clercq E, Pannecouque C. Non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 11: structural modulations of diaryltriazines with potent anti-HIV activity. Eur J Med Chem 2008;43:1230-1236. (Pubitemid 351734548)
16. Kerns RJ, Rybak MJ, Kaatz GW, Vaka F, Cha R, Grucz RG et al. Structural features of piperazinyl-linked ciprofloxacin dimers required for activity against drug-resistant strains of Staphylococcus aureus. Bioorg Med Chem Lett 2003;13:2109-2112. (Pubitemid 36694285)
17. Singh KK, Joshi SC, Mathela CS. Synthesis and in-vitro antibacterial activity of N-alkyl and N-aryl piperazine derivatives. Ind J Chem 2011;50(B):196-200.
18. Upadhayaya RS, Sinha N, Jain S, Kishore N, Chandra R, Arora SK. Optically active antifungal azoles: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-[2-[4-aryl-piperazin-1-yl]- ethyl]-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol. Bioorg Med Chem 2004;12:2225-2238. (Pubitemid 38471710)
19. Upadhayaya RS, Vandavasi JK, Kardile RA, Lahore SV, Dixit SS, Deokar HS et al. Novel quinoline and naphthalene derivatives as potent antimycobacterial agents. Eur J Med Chem 2010;45:1854-1867.
20. Kumar CS, Vinaya K, Chandra JN, Thimmegowda NR, Prasad SB, Sadashiva CT et al. Synthesis and antimicrobial studies of novel 1-benzhydryl-piperazine sulfonamide and carboxamide derivatives. J Enzyme Inhib Med Chem 2008;23:462-469.
21. Sunduru N, Gupta L, Chaturvedi V, Dwivedi R, Sinha S, Chauhan PM. Discovery of new 1,3,5-triazine scaffolds with potent activity against Mycobacterium tuberculosis H37Rv. Eur J Med Chem 2010;45:3335-3345.
22. Andries K, Verhasselt P, Guillemont J, Göhlmann HW, Neefs JM, Winkler H et al. A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis. Science 2005;307:223-227. (Pubitemid 40116230)
23. Rustomjee R, Diacon AH, Allen J, Venter A, Reddy C, Patientia RF et al. Early bactericidal activity and pharmacokinetics of the diarylquinoline TMC207 in treatment of pulmonary tuberculosis. Antimicrob Agents Chemother 2008;52:2831-2835.
24. Upadhayaya RS, Lahore SV, Sayyed AY, Dixit SS, Shinde PD, Chattopadhyaya J. Conformationally-constrained indeno[2,1-c] quinolines-a new class of anti-mycobacterial agents. Org Biomol Chem 2010;8:2180-2197.
25. Upadhayaya RS, Shinde PD, Sayyed AY, Kadam SA, Bawane AN, Poddar A et al. Synthesis and structure of azole-fused indeno[2,1-c] quinolines and their anti-mycobacterial properties. Org Biomol Chem 2010;8:5661-5673.
26. Upadhayaya RS, Shinde PD, Kadam SA, Bawane AN, Sayyed AY, Kardile RA et al. Synthesis and antimycobacterial activity of prodrugs of indeno[2,1-c] quinoline derivatives. Eur J Med Chem 2011;46:1306-1324.
27. Xiong YZ, Chen FE, Balzarini J, De Clercq E, Pannecouque C. Non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 13: synthesis of fluorine-containing diaryltriazine derivatives for in vitro anti-HIV evaluation against wild-type strain. Chem Biodivers 2009;6:561-568.
28. Patel RV, Kumari P, Chikhalia KH. Novel s-triazinyl piperazines: Design, synthesis, characterization and anti-microbial activity. Arch Appl Sci Res 2010;2:232-240.
29. Gillespie SH. Medical microbiology-Illustrated, Butterworth Heinemann Ltd., United Kingdom: 1994:234-247.
30. Hawkey PM, Lewis DA. Medical bacteriology-a practical approach. Oxford University Press, United Kingdom: 1994:181-194.
31. Anargyros P, Astill DS, Lim IS. Comparison of improved BACTEC and Lowenstein-Jensen media for culture of mycobacteria from clinical specimens. J Clin Microbiol 1990;28:1288-1291. (Pubitemid 20194420)
32. Isenberg HD. Clinical microbiology procedures handbook, vol. 1, American Society for Microbiology, Washington, D.C. 1992.
33. Patel NB, Khan IH, Rajani SD. Antimycobacterial and antimicrobial study of new 1,2,4-triazoles with benzothiazoles. Arch Pharm (Weinheim) 2010;343:692-699.
34. Dandia A, Arya K, Sati M, Sarawgi P. Green chemical synthesis of fluorinated 1,3,5-triaryl-s-triazines in aqueous medium under microwaves as potential antifungal agents. J Fluorine Chem 2004;125:1273-1277.