Synthesis, anticandidal activity and cytotoxicity of some tetrazole derivatives

References

• Pappas PG, Rex JH, Sobel JD, et al. Guidelines for treatment of candidiasis. Clin Infect Dis 2004;38:161–89
   PubMed Web of Science ®Google Scholar
• Rees JR, Pinner RW, Hajjeh RA. The epidemiological features of invasive mycotic infections in the San Francisco bay area, 1992–1993: results of population-based laboratory active surveillance. Clin Infect Dis 1998;27:1138–47
   PubMed Web of Science ®Google Scholar
• Polak A. The past, present and future of antimycotic combination therapy. Mycoses 1999;42:355–70
   PubMed Web of Science ®Google Scholar
• Fostel JM, Lartey PA. Emerging novel antifungal agents. Drug Discov Today 2000;5:25–32
   PubMed Web of Science ®Google Scholar
• Bodey GP. Azole antifungal agents. Clin Infect Dis 1992;14:161–9
   PubMed Web of Science ®Google Scholar
• Sheehan DJ, Hitchcock CA, Sıbley CM. Current and emerging azole antifungal agents. Clin Microbiol Rev 1999;12:40–79
   PubMed Web of Science ®Google Scholar
• Maertens JA. History of the development of azole derivatives. Clin Microbiol Infect 2004;10:1–9
   PubMed Web of Science ®Google Scholar
• Rossello A, Bertini S, Lapucci A, et al. Synthesis, antifungal activity, and molecular modeling studies of new inverted oxime ethers of oxiconazole. J Med Chem 2002;45:4903–12
   PubMed Web of Science ®Google Scholar
• Rajasekaran A, Thampi PP. Synthesis and analgesic evaluation of some 5-[β-(10-phenothiazinyl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles. Eur J Med Chem 2004;39:273–9
   PubMed Web of Science ®Google Scholar
• Dhayanithi V, Syed SS, Kumaran K, et al. Synthesis of selected 5-thio-substituted tetrazole derivatives and evaluation of their antibacterial and antifungal activities. J Serb Chem Soc 2011;76:165–75
   Web of Science ®Google Scholar
• Kraft A, Osterod F, Frohlich R. Bidirectional association of branched noncovalent complexes of tetrazoles and 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene in solution. J Org Chem 1999;64:6425–33
   Web of Science ®Google Scholar
• Klaubert DH, Sellstedt JH, Guinosso CJ, et al. 5-Tetrazolecarboxamides and their salts: new orally active antiallergy agents. J Med Chem 1981;24:748–52
   PubMedGoogle Scholar
• El-Sayed WA, Megeid REA, Abbas HS. Synthesis and antimicrobial activity of new 1-[(tetrazol-5-yl)methyl]indole derivatives, their 1,2,4-triazole thioglycosides and acyclic analogs. Arch Pharm Res 2011;34:1085–96
   PubMedGoogle Scholar
• Sabbah M, Fontaine F, Grand L, et al. Synthesis and biological evaluation of new N-acyl-homoserine-lactone analogues, based on triazole and tetrazole scaffolds, acting as LuxR-dependent quorum sensing modulators. Bioorg Med Chem 2012;20:4727–36
   PubMed Web of Science ®Google Scholar
• Rostom SAF, Ashour HMA, Abd El Razik HA, et al. Azole antimicrobial pharmacophore-based tetrazoles: synthesis and biological evaluation as potential antimicrobial and anticonvulsant agents. Bioorg Med Chem 2009;17:2410–22
   PubMed Web of Science ®Google Scholar
• Meanwell NA. Synopsis of some recent tactical application of bioisosteres in drug design. J Med Chem 2011;54:2529–91
   PubMed Web of Science ®Google Scholar
• Myznikov LV, Hrabalek A, Koldobskii GI. Drugs in the tetrazole series. Chem Heterocycl Comp 2007;43:1–9
   Google Scholar
• Adamec J, Waisser K, Kunes J, Kaustova J. A note on the antitubercular activities of 1-aryl-5-benzylsulfanyltetrazoles. Arch Pharm 2005;338:385–9
   PubMed Web of Science ®Google Scholar
• Mohite PB, Pandhare RB, Khanage SG, Bhaskar VH. Synthesis and in vitro antimicrobial activity of some novel chalcones containing 5-phenyl tetrazole. Acta Pharma Sci 2010;52:505–10
   Google Scholar
• Cosgrove CE, Laforge RA. Tetrazole derivatives I. Tetrazole alkamine ethers. J Org Chem 1956;21:197–200
   Google Scholar
• Haydu SP, Bardley J, Hughes DTD. Inhibitory effect of oral doxantrazole on asthma induced by allergen inhalation. Br Med J 1975;3:283–4
   PubMedGoogle Scholar
• Toney JH, Fitzgerald PMD, Sharma NG, et al. Antibiotic sensitization using biphenyl tetrazoles as potent inhibitors of bacteroides fragiris metallo-β-lactamase. Chem Biol 1998;5:185–96
   PubMedGoogle Scholar
• Berghmans S, Hunt J, Roach A, Goldsmith P. Zebrafish offer the potential for a primary screen to identify a wide variety of potential anticonvulsants. Epilepsy Res 2007;75:18–28
   PubMed Web of Science ®Google Scholar
• Khanage SG, Mohite PB, Pandhareb RB, Raju SA. Study of analgesic activity of novel 1,2,4-triazole derivatives bearing pyrazole and tetrazole moiety. J Pharm Res 2011;4:3609–11
   Google Scholar
• Maxwell JR, Wasdahl DA, Wolfson AC, Stenberg VI. Synthesis of 5-aryl-2H-tetrazoles, 5-aryl-2H-tetrazole-2-acetic acids, and [(4-phenyl-5-aryl-4H-1,2,4-triazol-3-yl)thio]acetic acids as possible superoxide scavengers and antiinflammatory agents. J Med Chem 1984;27:1565–70
   PubMed Web of Science ®Google Scholar
• Bhaskar VH, Mohite PB. Synthesis, characterization and evaluation of anticancer activity of some tetrazole derivatives. J Optoelectron Biomed M 2010;2:249–59
   Google Scholar
• Ueda I, Ishii K, Sinozaki K, Htanaka M. Antiulcer agents. II: synthesis and gastric acid antisecretory activity of N-[3-{3-(piperidinomethyl)phenoxy}propyl]-4-(1-methyl-1H-tetrazol-5-ylthio)butanamide and related compounds. Chem Pharm Bull 1991;39:1430–5
   PubMed Web of Science ®Google Scholar
• Bhaskar VH, Mohite PB. Synthesis analgesic, anti-inflammatory and antimicrobial activities of some 1-[5-(substituted phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-5-phenyl-1H-tetrazole. J Optoelectron Biomed M 2011;3:7–16
   Google Scholar
• Singh H, Chawla AS, Kapoor VK, et al. Progress in medicinal chemistry. In: Ellis GP, West GB, eds. Medicinal chemistry of tetrazoles. Amsterdam: Elsevier/North Holland; 1980:151–73
   Google Scholar
• Upadhayaya RS, Jain S, Sinha N, et al. Synthesis of novel substituted tetrazoles having antifungal activity. Eur J Med Chem 2004;39:579–92
   PubMed Web of Science ®Google Scholar
• Matysiak J, Niewiadomy A, Krajewska-Kułak E, Mącik-Niewiadomy G. Synthesis of some 1-(2,4-dihydroxythiobenzoyl)imidazoles, -imidazolines and -tetrazoles and their potent activity against Candida species. IL Farmaco 2003;58:455–61
   PubMedGoogle Scholar
• Roh J, Vávrová K, Hrabálek A. Synthesis and functionalization of 5-substituted tetrazoles. Eur J Org Chem 2012;31:6101–18
   Google Scholar
• Kanakaraju S, Prasanna B, Chandramouli GVP. An efficient one-pot three-component synthesis of novel sulfanyl tetrazoles using ionic liquids. J Chem 2013;2013:1--6
   Google Scholar
• Segura-Cabrera A, Pérez MAR. Structure-based prediction of Mycobacterium tuberculosis shikimate kinase inhibitors by high-throughput virtual screening. Bioorg Med Chem Lett 2008;18:3152–7
   PubMed Web of Science ®Google Scholar
• Webster SP, Binnie M, McConnell KMM, et al. Modulation of 11b-hydroxysteroid dehydrogenase type 1 activity by 1,5-substituted 1H-tetrazoles. Bioorg Med Chem Lett 2010;20:3265–71
   PubMed Web of Science ®Google Scholar
• Morita H, Takeda M, Yoshimura T, et al. Novel type elimination reactions of sulfoxides bearing several heteroaromatics: trapping of sulfines with 2,3-dimethyl-1,3-butadiene. J Org Chem 1999;64:6730–7
   PubMed Web of Science ®Google Scholar
• Webster SP, Seckl JR, Walker BR. 1,5-substituted-1h-tetrazole 11beta-hydroxysteroid dehydrogenase type 1 inhibitors, Patent GB 2429975 A 20070314, UK; 2007
   Google Scholar
• Hakonarson H, Gurney ME, Halapi E. Methods of diagnosis and treatment for asthma and other respiratory diseases based on haplotype, Patent US 20060014165 A1 20060119, USA; 2006
   Google Scholar
• Hakonarson H, Gurney ME, Halapi E. Methods of diagnosis and treatment for asthma and other respiratory diseases based on haplotype association related applications, Patent WO 2005007144 A2 20050127, USA; 2005
   Google Scholar
• Hudkins RL, Mallamo JP, Hamano M, et al. Selected derivatives of K-252a, Patent US 6306849 B1 20011023, USA; 2001
   Google Scholar
• Hudkins RL, Mallamo JP, Hamano M, et al. K-252 derivatives as protein kinase C inhibitors, their preparation and formulations containing them, Patent WO 9746565 A1 19971211, USA; 1997
   Google Scholar
• Nishi T, Uno T, Koga Y, Chu GN. Tetrazole derivatives and antiulcer composition containing them, EP 240015 A2 19871007; 1987
   Google Scholar
• Goldfarb DS. Method for altering the lifespan of eukaryotic organisms, US 20090163545 A1 20090625, USA; 2009
   Google Scholar
• Koneman EW, Allen SD, Janda WM, et al. Color atlas and textbook of diagnostic microbiology, mycology. Philadelphia, PA: Lippincott-Williams and Wilkins; 1997:983–1057
   Google Scholar
• Mossmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63
   PubMed Web of Science ®Google Scholar
• Keiser K, Johnson CC, Tipton DA. Cytotoxicity of mineral trioxide aggregate using human periodontal ligament fibroblasts. J Endod 2000;26:288–91
   PubMed Web of Science ®Google Scholar