Molecular docking, synthesis, and antimycobacterial activities of pyrrolyl hydrazones and their copper complexes

References

• Wolinsky E. Tuberculosis. In: Wyngaarden JB, Smith LH, Jr, Bennett JC, editors. Cecil Textbook of Medicine. Vol 2. 19th ed. Philadelphia, PA: WB Saunders Company; 1992:1733–1742.
   Google Scholar
• Sensi P, Grass IGG. Antimycobacterial agents. In: Burger A, Wolff ME, editors. Burger’s Medicinal Chemistry and Drug Discovery. Vol 2. 5th ed. New York, NY: John Wiley and Sons; 1996:575–635.
   Google Scholar
• World Health Organization. Global Tuberculosis Report. Geneva, Switzerland: WHO; 2013.
   Google Scholar
• Zumla A, Nahid P, Cole ST. Advances in the development of new tuberculosis drugs and treatment regimens. Nat Rev Drug Discov. 2013;12:388–404.
   PubMed Web of Science ®Google Scholar
• Goldman RC, Plumley KV, Laughon BE. The evolution of extensively drug resistant tuberculosis (XDR-TB): history, status and issues for global control. Infect Disord Drug Targets. 2007;7:73–91.
   PubMedGoogle Scholar
• Benatar SR. Extensively drug resistant tuberculosis – problem will get worse in South Africa unless poverty is alleviated. Br Med J. 2006;333(7570):705.
   Google Scholar
• Lawn SD, Wilkinson R. Extensively drug resistant tuberculosis – a serious wake-up call for global health. Br Med J. 2006;333:559–560.
   PubMed Web of Science ®Google Scholar
• Dahle UR. Extensively drug resistant tuberculosis – beware patients lost to follow-up. Br Med J. 2006;333(7570):705.
   Google Scholar
• Gandhi NR, Moll A, Sturm AW, et al. Extensively drug-resistant tuberculosis as a cause of death in patients co-infected with tuberculosis and HIV in a rural area of South Africa. Lancet. 2006;368:1575–1580.
   PubMed Web of Science ®Google Scholar
• Manissero D, Fernandez K. Extensive drug-resistant TB: a threat for Europe? Euro Surveill. 2006;11:E060928.2.
   Google Scholar
• Takayama K, Wang C, Besra GS. Pathway to synthesis and processing of mycolic acids in Mycobacterium tuberculosis. Clin Microbiol Rev. 2005;18:81–101.
   PubMed Web of Science ®Google Scholar
• Takayama K, Wang L, David HL. Effect of isoniazid on the in vivo mycolic acid synthesis, cell growth, and viability of Mycobacterium tuberculosis. Antimicrob Agents Chemother. 1972;2(1):29–35.
   Web of Science ®Google Scholar
• Quemard A, Laneelle G, Lacave C. Mycolic acid synthesis: a target for ethionamide in mycobacteria? Antimicrob Agents Chemother. 1992;36(6):1316–1321.
   PubMed Web of Science ®Google Scholar
• Banerjee A, Dubnau E, Quemard A, et al. inhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis. Science. 1994;263:227–230.
   Google Scholar
• Joshi SD, Dixit SR, More UA, Aminabhavi TM, Kulkarni VH, Gadad AK. Enoyl ACP reductase as effective target for the synthesized novel antitubercular drugs: a-state-of-the-art. Mini Rev Med Chem. 2014;14:678–693.
   PubMed Web of Science ®Google Scholar
• Aminabhavi TM, Biradar NS, Patil SB, Hoffman DE. Structural and biological studies on benzimidazolyl amino acid complexes of dimethyldichlorosilane. Inorg Chim Acta. 1986;125:125–128.
   Web of Science ®Google Scholar
• Jaiswal V, Gupta SR, Rastogi RB, Kumar R, Singh VP. Evaluation of antiwear activity of substituted benzoylhydrazones and their copper(II) complexes in paraffin oil as efficient low SAPS additives and their interactions with the metal surface using density functional theory. J Mater Chem A. 2015;3:5092–5109.
   Web of Science ®Google Scholar
• Sutradhar M, Kirillova MV, Guedes da Silva MFC, Liu CM, Pombeiro AJL. Tautomeric effect of hydrazone Schiff bases in tetranuclear Cu(II) complexes: magnetism and catalytic activity towards mild hydrocarboxylation of alkanes. Dalton Trans. 2013;42:16578–16587.
   PubMed Web of Science ®Google Scholar
• Nitschke JR. Construction, substitution, and sorting of metallo-organic structures via subcomponent self-assembly. Acc Chem Res. 2007;40:103–107.
   PubMed Web of Science ®Google Scholar
• Opstal T, Verpoort F. Synthesis of highly active ruthenium indenylidene complexes for atom-transfer radical polymerization and ring-opening-metathesis polymerization. Angew Chem Int Ed Engl. 2003;42:2876–2884.
   PubMed Web of Science ®Google Scholar
• Chew ST, Lo KM, Lee SK, et al. Copper complexes with phosphonium containing hydrazone ligand: topoisomerase inhibition and cytotoxicity study. Eur J Med Chem. 2014;76:397–407.
   PubMed Web of Science ®Google Scholar
• Joseph J, Nagashri K, Janaki GB. Novel metal based anti-tuberculosis agent: synthesis, characterization, catalytic and pharmacological activities of copper complexes. Eur J Med Chem. 2012;49:151–163.
   PubMed Web of Science ®Google Scholar
• Patil M, Hunoor R, Gudasi K. Transition metal complexes of a new hexadentate macroacyclic N2O4-donor Schiff base: inhibitory activity against bacteria and fungi. Eur J Med Chem. 2010;45:2981–2986.
   PubMed Web of Science ®Google Scholar
• Liu ZC, Wang BD, Wang B, et al. Synthesis of heterobimetallic complexes: In vitro DNA binding, cleavage and antimicrobial studies. J Med Chem. 2010;45:5353–5361.
   Google Scholar
• Kaabi K, Zeller M, Ferretti V, Silva PPS, Nasr BC. Iron(II), Nickel(II), Copper(II) and Zinc(II) Complexes of 2,4-dinitro-6(pyridine-2-ylmethylamino) methylphenolate: synthesis, characterization and Antimicrobial Activities. Inorg Chim Acta. 2012;388:52–59.
   Web of Science ®Google Scholar
• Singh AP, Kaushik NK, Verma AK, Hundal G, Gupta R. Synthesis, structure and biological activity of copper(II) complexes of 4-(2-pyridylmethyl)-1,7-dimethyl-1,4,7-triazonane-2,6-dione and 4-(2-pyridylethyl)-1,7-dimethyl-1,4,7-triazonane-2,6-dione. Eur J Med Chem. 2009;44:1607–1614.
   PubMed Web of Science ®Google Scholar
• Horsfall JG. Principles of Fungicidal Action. Waltham, MA: Chronica Botanica Co.; 1956:141.
   Google Scholar
• Arman P, Wain RL. Studies upon the copper fungicides: X. The role of leaf exudates in the solution of copper from Bordeaux mixture. Ann Appl Biol. 1958;46:366–371.
   Web of Science ®Google Scholar
• Raman N, Jeyamurugan R, Senthilkumar R, Rajkapoor B, Franzblau SG. In vivo and in vitro evaluation of highly specific thiolate carrier group copper(II) and zinc(II) complexes on Ehrlich ascites carcinoma tumor model. Eur J Med Chem. 2010;45:5438–5451.
   PubMed Web of Science ®Google Scholar
• Li Y, Yang ZY, Wu JC. Synthesis, crystal structures, biological activities and fluorescence studies of transition metal complexes with 3-carbaldehyde chromone thiosemicarbazone. Eur J Med Chem. 2010;45:5692–5701.
   PubMed Web of Science ®Google Scholar
• Sayed M, Zayed MAA, Gehad MG. Tetradentate-arm Schiff base derived from the condensation reaction of 3,3′-dihydroxybenzidine, glyoxal/diacetyl and 2-aminophenol: designing, structural elucidation and properties of their binuclear metal(II) complexes. Arab J Chem. 2010;3:103–113.
   Google Scholar
• Joshi SD, More UA, Pansuriya K, Aminabhavi TM, Gadad AK. Synthesis and molecular modeling studies of novel pyrrole analogs as antimycobacterial agents. J Saudi Chem Soc. 2013. doi:10.1016/j.jscs.2013.09.002.
   Google Scholar
• More UA, Joshi SD, Aminabhavi TM, Gadadd AK, Nadagouda MN, Kulkarni VH. Design, synthesis, molecular docking and 3D-QSAR studies of potent inhibitors of enoylacyl carrier protein reductase as potential antimycobacterial agents. Eur J Med Chem. 2014;71:199–218.
   PubMed Web of Science ®Google Scholar
• Joshi SD, Dixit SR, More UA, Rai S, Kulkarni VH. Molecular modeling, synthesis, antibacterial and antitubercular activities of some novel pyrrolyl 1,2,4-triazole derivatives. Indo Am J Pharm Res. 2014;4(5):2323–2338.
   Google Scholar
• Joshi SD, More UA, Dixit SR, Dubey D, Tripathi A, Kulkarni VH. Discovering potent inhibitors against the enoyl-acyl carrier protein reductase (InhA) of mycobacterium tuberculosis: structure based design, synthesis and antimicrobial activity of quinoline hydrazones. Indo Am J Pharm Res. 2014;4(2):864–877.
   Google Scholar
• Tripos International. Sybyl-X 2.0. St Louis, MO: Tripos International; 2012.
   Google Scholar
• Jain AN. Scoring noncovalent protein-ligand interactions: a continuous differentiable function tuned to compute binding affinities. J Comput Aided Mol Des. 1996;10:427–440.
   PubMed Web of Science ®Google Scholar
• Jain AN. Surflex: fully automatic flexible molecular docking using a molecular similarity-based search engine. J Med Chem. 2003;46:499–511.
   PubMed Web of Science ®Google Scholar
• Clark M, Cramer RD, Opdenbosch VN. Validation of the general purpose tripos 5.2 force field. J Comput Chem. 1989;10:982–1012.
   Web of Science ®Google Scholar
• Ai Y, Wang ST, Sun PH, Song FJ. Molecular modeling studies of 4,5-dihydro-1H-pyrazolo[4,3-H] quinazoline derivatives as potent CDK2/cyclin a inhibitors using 3D-QSAR and docking. Int J Mol Sci. 2010;11:3705–3724.
   Web of Science ®Google Scholar
• Lan P, Chen WN, Chen WM. Molecular modeling studies on imidazo[4,5-b]pyridine derivatives as Aurora A kinase inhibitors using 3D-QSAR and docking approaches. Eur J Med Chem. 2011;46:77–94.
   PubMed Web of Science ®Google Scholar
• Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: a novel class of potential antibacterial and antitubercular agents. Eur J Med Chem. 2008;43:1989–1996.
   PubMed Web of Science ®Google Scholar
• Lourenco MCS, deSouza MVN, Pinheiro AC, et al. Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues. ARKIVOC. 2007;15:181–191.
   Google Scholar
• Goto S, Jo K, Kawakita T, Mitsuhashi S, Nishino T, Ohsawa N. Determination method of minimum inhibitory concentrations. Chemotherapy. 1981;29:76–79.
   Google Scholar
• Winter CA, Risley EA, Nuss GW. Carrageenin-induced edemas in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med. 1962;111:544–547.
   PubMed Web of Science ®Google Scholar