Synthesis and antitubercular activity of heterocycle substituted diphenyl ether derivatives

References

• World Health Organisation. http://www.who.int/tb. 2008 Tuberculosis Facts.
   Google Scholar
• Nunn P, Williams B, Floyd K, Dye C, Elzinga G, Raviglione M. Nat Rev Immunol 2005;5:819–826.
   PubMed Web of Science ®Google Scholar
• World Health Organization. Bridging the gaps: the world health report, Geneva: The Organization. (1995).
   Google Scholar
• World Health Organization report on TB epidemic. Global TB programme, Geneva: The Organization. (1997).
   Google Scholar
• World Health Organization. Tuberculosis; Fact Sheet No.104 (2002). Site accessed: www.who.int/mediacentre/factsheets/who104/en/index.html.
   Google Scholar
• El Sayed KA, Bartyzel P, Shen XY, Perry TL, Zjawiony JK, Hamann MT. Marine natural products as antituberculosis agents. Tetrahedron 2000;56:949–953.
   Web of Science ®Google Scholar
• Goldberg MJ. Antituberculosis agents. Med Clin North Am 1988;72:661–668.
   PubMed Web of Science ®Google Scholar
• Maranetra KN. Quinolones and multidrug-resistant tuberculosis. Chemotherapy 1999;45:3–11.
   PubMed Web of Science ®Google Scholar
• Berning SE. The role of fluoroquinolones in tuberculosis today. Drugs 2001;61:9–18.
   PubMed Web of Science ®Google Scholar
• Reddy VM, Nadadhur G, Daneluzzi DD, Osullivan JF and Gangadharam PRJ. Antituberculosis activities of clofazimine and its new analogs B4154 and B4157. Antimicrob Agents Chemother 1996;40:633–636.
   PubMed Web of Science ®Google Scholar
• Barry CE. New horizons in the treatment of tuberculosis. Biochem Pharmacol 1997;54:1165–1172.
   PubMed Web of Science ®Google Scholar
• Pasquato KFM and Ferreira EI. An approach for the rational design of new antitubercular agents. Curr Drug Targets 2001;2:427–437.
   PubMed Web of Science ®Google Scholar
• Brenan PJ, Nikaido H. The envelope of mycobacteria. Annu Rev Biochem 1995;64:29–63.
   PubMed Web of Science ®Google Scholar
• Barry CE III, Lee RE, Mdluli K, Sampson AE, Schroeder BG, Slayden RA, Yaun Y. Mycolic acid structure, biosynthesis and physiological functions. Prog Lipid Res 1998;37:143–179.
   PubMed Web of Science ®Google Scholar
• Kolattukudy PE, Fernandes ND, Azad AK, Fitzmaurice AM, Sirakova TD. Biochemistry and molecular genetics of cell-wall lipid biosynthesis in 16 mycobacteria. Mol Microbiol 1997;24:263–270.
   PubMed Web of Science ®Google Scholar
• Bergler H, Fuchsbichler S, Hogenauer G, Turnowsky F. The enoyl-[acyl-carrier-protein] reductase (FabI) of Escherichia coli, which catalyzes a key regulatory step in fatty acid biosynthesis, accepts NADH and NADPH as cofactors and is inhibited by palmitoyl-CoA. Eur J Biochem 1996;242:689–694.
   PubMedGoogle Scholar
• Stewart MJ, Parikh S, Xiao G, Tonge PJ, Kisker C. Structural basis and mechanism of enoyl reductase inhibition by triclosan. J Mol Biol 1999;290:859–865.
   PubMed Web of Science ®Google Scholar
• Rozwarski DA, Vilcheze C, Sugantino M, Bittman R, Sacchettini JC. Crystal structure of the Mycobacterium tuberculosis enoyl-ACP reductase, InhA, in complex with NAD+ and a C16 fatty substrate. J Biol Chem 1999;274:15582–15589.
   PubMed Web of Science ®Google Scholar
• Boshoff HI, Mizrahi V, Barry CE III. Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I. J Bacteriol 2002;184:2167–2172.
   PubMed Web of Science ®Google Scholar
• Zimhony O, Cox JS, Welch JT, Vilcheze C, Jacobs WR Jr. Pyrazinamide inhibits the eukaryotic-like fatty acid synthetase I (FASI) of Mycobacterium tuberculosis. Nat Med 2000);6:1043–1047.
   PubMed Web of Science ®Google Scholar
• Schweizer HP. Triclosan: A widely used biocide and its link to antibiotics. FEMS Microbiol Lett 2001;202:1–7.
   PubMed Web of Science ®Google Scholar
• Regos J, Zak O, Solf R, Vischer WA, Weirich EG. Antimicrobial spectrum of triclosan, a broad-spectrum antimicrobial agent for topical application. II. Comparison with some other antimicrobial agents. Dermatologica 1979;1158:72–79.
   Google Scholar
• Vischer WA, Regos J. Antimicrobial spectrum of triclosan, a broad-spectrum antimicrobial agent for topical application. Zentralbl Bakteriol [Orig A] 1974;226:376–389.
   Google Scholar
• McMurry LM, Oethinger M, Levy SB. Triclosan targets lipid synthesis. Nature 1998;394:531–532.
   PubMed Web of Science ®Google Scholar
• Heath RJ, Yu YT, Shapiro MA, Olson E, Rock CO. Broad spectrum antimicrobial biocides target the FabI component of fatty acid synthesis. J Biol Chem 1998;273:30316–30320.
   PubMed Web of Science ®Google Scholar
• Ward WH, Holdgate GA, Rowsell S, McLean EG, Pauptit RA, Clayton E, Nichols W, Colls JG, Minshull CA, Jude DA, Mistry A, Timms D, Camble R, Hales NJ, Britton CJ, Taylor IW. Kinetic and structural characteristics of the inhibition of enoyl (acyl carrier protein) reductase by triclosan. Biochemistry 1999;38:12514–12525.
   PubMed Web of Science ®Google Scholar
• Levy CW, Roujeinikova A, Sedelnikova S, Baker PJ, Stuitje AR. Molecular basis of triclosan activity. Nature 1999;398:383–384.
   PubMed Web of Science ®Google Scholar
• Stewart MJ, Parikh S, Xiao G, Tonge PJ, Kisker C. Structural basis and mechanism of enoyl reductase inhibition by triclosan. J Mol Biol 1999;290:859–865.
   PubMed Web of Science ®Google Scholar
• Roujeinikova A, Levy CW, Rowsell S, Sedelnikova S, Baker PJ, Minshull CA, Mistry A, Colls JG, Camble R, Stuitje AR, Slabas AR, Rafferty JB, Pauptit RA, Viner R, Rice DW. Crystallographic analysis of triclosan bound to enoyl reductase. J Mol Biol 1999;294:527–535.
   PubMed Web of Science ®Google Scholar
• Heath RJ, Li J, Roland GE, Rock CO. Inhibition of the Staphylococcus aureus NADPH-dependent enoyl-acyl carrier protein reductase by triclosan and hexachlorophene. J Biol Chem 2001;275:4654–4659.
   Web of Science ®Google Scholar
• Marcinkeviciene J, Jiang W, Kopcho LM, Locke G, Luo Y. Enoyl-ACP reductase (FabI) of Haemophilus influenzae: steady-state kinetic mechanism and inhibition by triclosan and hexachlorophene. Arch Biochem Biophys 2001;390:101–108.
   PubMed Web of Science ®Google Scholar
• McMurry LM, McDermott PF, Levy SB. Genetic evidence that InhA of Mycobacterium smegmatis is a target for triclosan. Antimicrob Agents Chemother 1999;43:711–713.
   PubMed Web of Science ®Google Scholar
• Parikh SL, Xiao G, Tonge, PJ. Inhibition of InhA, the enoyl reductase from Mycobacterium tuberculosis, by triclosan and isoniazid. Biochemistry 2000;39:7645–7650.
   PubMed Web of Science ®Google Scholar
• Kuo MR, Morbidoni HR, Alland D, Sneddon S F, Gourlie BB. Targeting tuberculosis and malaria through inhibition of enoyl reductase: Compound activity and structural data. J Biol Chem 2003;278:20851–20859.
   PubMed Web of Science ®Google Scholar
• Surolia N, Surolia A. Triclosan offers protection against blood stages of malaria by inhibiting enoyl-ACP reductase of Plasmodium falciparum. Nat Med 2001;7:167–173.
   PubMed Web of Science ®Google Scholar
• Kapoor M, Dar MJ, Surolia N, Surolia A. Kinetic determinants of the interaction of enoyl-ACP reductase from Plasmodium falciparum with its substrates and inhibitors. Biochem Biophys Res Commun 2001;289:832–837.
   PubMed Web of Science ®Google Scholar
• Perozzo R, Kuo M, bir Singh Sidhu A, Valiyaveettil JT, Bittman R, Jacobs WR Jr, Fidock DA, Sacchettini JC. Structural elucidation of the specificity of the antibacterial agent triclosan for malarial enoyl ACP reductase. J Biol Chem 2002;277:13106–13114.
   PubMed Web of Science ®Google Scholar
• Vincent CB, Twomey D. Derivatives of diploicin. Proc Royal Irish Acad 1950;53:55–59.
   Google Scholar
• Dayan FE, Ferreira D, Wang Y-H Khan, IA, McInroy JA, Pan Z. A pathogenic fungi diphenyl ether phytotoxin targets plant enoyl (acyl carrier protein) reductase. Plant Physiol 2008;147:1062–1071.
   PubMed Web of Science ®Google Scholar
• Sivarana S, Sullivan TJ, Johnson F, Novichenok P, Cui G, Simmerling C, Tonge PJ Inhibition of the bacterial Enoyl reductase FabI by triclosan: A structure-reactivity analysis of FabI inhibition by triclosan analogues. J Med Chem 2004;47:509–518.
   PubMed Web of Science ®Google Scholar
• Kini SG, Bhat AR, Bryant B, Williamson JS, Dayan FE. Synthesis, antitubercular activity and docking study of novel cyclic azole substituted diphenyl ether derivatives. Eur J Med Chem 2009;44:492–500.
   PubMed Web of Science ®Google Scholar
• Dosages and Pharmacokinetics of antituberculosis medications-a report in India. [13–06–2006] Site accessed: http://www.angelfire.com/indie/tbindia/attdrugs.html
   Google Scholar
• Furniss BS, Hannaford AJ, Rogers V, Smith PWG, Tatchell AR. Aromatic carboxylic acids, In: Vogel’s Textbook of Practical Organic Chemistry, Ed IV London: Longman Group, 1980:824.
   Google Scholar
• Udupi R.Ph.D thesis on “Studies on the synthesis of substituted Triazoles, Azetidinones, Quinazolinones and related compounds for possible antitubercular activity and other pharmacological profiles”;.
   Google Scholar
• Watt B, Rayner A, Harris G, Mackie, McCartney. Chapter 18. In: Colle JG, Fraser AG, Marmion BP, Simmons A. Eds Practical Medical Microbiology. New York: Churchill Livingstone, 1996:331–335.
   Google Scholar
• Sambrook J, Fritsch E, Maniatis T. In Molecular Cloning, A Laboratory Manual. 2nd edition, New York: Cold Spring Harbor Laboratory Press, 1989.
   Google Scholar