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Original Articles

Synthesis and antitumor activity of tetrahydrocarbazole hybridized with dithioate derivatives

Pages 308-315 | Received 31 Mar 2014, Accepted 05 May 2014, Published online: 05 Jun 2014

References

  • Turan-Zitouni G, Ozdemir A, Güven K. Synthesis of some 1-[(N,N-disubstituted thiocarbamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives and investigation of their antibacterial and antifungal activities. Arch Pharm Chem Life Sci 2005;338:96–104
  • Guzel, O, Salman A. Synthesis, antimycobacterial and antitumor activities of new (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl N,Ndisubstituted dithiocarbamate/O-alkyldithiocarbonate derivatives. Bioorg Med Chem 2006;14:7804–15
  • Ren JL, Zhang E, Ye XW, et al. Design, synthesis and antibacterial evaluation of novel AHL analogues. Bioorg Med Chem Lett 2013;23:4154–6
  • Uchide N, Ohyama K, Bessho T, et al. Effect of antioxidants on apoptosis induced by influenza virus infection: inhibition of viral gene replication and transcription with pyrrolidine dithiocarbamate. Antiviral Res 2002;56:207–17
  • Si X, McManus BM, Zhang J, et al. Pyrrolidine dithiocarbamate reduces coxsackievirus B3 replication through inhibition of the ubiquitin-proteasome pathway. J Virol 2005;79:8014–23
  • El Ashry EH, Amer MR, Abdalla OM, et al. Synthesis, biological evaluation, and molecular docking studies of benzyl, alkyl and glycosyl [2-(arylamino)-4,4-dimethyl-6-oxo-cyclohex-1-ene]carbodithioates, as potential immunomodulatory and immunosuppressive agents. Bioorg Med Chem 2012;20:3000–8
  • Karali N, Apak I, Ozkirimli S, et al. Synthesis and pharmacology of new dithiocarbamic acid esters derived from phenothiazine and diphenylamine. Arch Pharm Chem Life Sci 1999;332:422–6
  • Zahran MAH, Salem TAR, Samaka RM, et al. Design, synthesis and antitumor evaluation of novel thalidomide dithiocarbamate and dithioate analogs against Ehrlich ascites carcinoma-induced solid tumor in Swiss albino mice. Bioorg Med Chem 2008;16:9708–18
  • Li RD, Zhang X, Li QY, et al. Novel EGFR inhibitors prepared by combination of dithiocarbamic acid esters and 4-anilinoquinazolines. Bioorg Med Chem Lett 2011;21:3637–40
  • Supuran CT, Briganti F, Tilli S, et al. Carbonic anhydrase inhibitors: sulfonamides as antitumor agents? Bioorg Med Chem 2001;9:703–14
  • Cao SL, Feng YP, Jiang YY, et al. Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains. Bioorg Med Chem Lett 2005;15:1915–17
  • Wang XJ, Xu HW, Guo LL, et al. Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates. Bioorg Med Chem Lett 2011;21:3074–7
  • Huang W, Ding Y, Miao Y, et al. Synthesis and antitumor activity of novel dithiocarbamate substituted chromones. Eur J Med Chem 2009;44:3687–96
  • Duan YC, Ma YC, Zhang E, et al. Design and synthesis of novel 1,2,3-triazole-dithiocarbamate hybrids as potential anticancer agents. Eur J Med Chem 2013;62:11–19
  • Duan YC, Zheng YC, Li XC, et al. Design, synthesis and antiproliferative activity studies of novel 1,2,3-triazoleedithiocarbamateeurea hybrids. Eur J Med Chem 2013;64:99–110
  • Cao SL, Wang Y, Zhu L, et al. Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates. Eur J Med Chem 2010;45:3850–7
  • Cao SL, Han Y, Yuan CZ, et al. Synthesis and antiproliferative activity of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline. Eur J Med Chem 2013;64:401–9
  • Noboru U, Kunio O. Antiviral function of pyrrolidine dithiocarbamate against influenza virus: the inhibition of viral gene replication and transcription. J Antimicrob Chemother 2003;52:8–10
  • Chen D, Dou QP. New uses for old copper-binding drugs: converting the pro-angiogenic copper to a specific cancer cell death inducer. Expert Opin Ther Targets 2008;12:739–48
  • Cvek B, Dvorak ZT. Targeting of nuclear factor-kB and proteasome by dithiocarbamate complexes with metals. Curr Pharm Des 2007;30:3155–67
  • Schonenberger VH, Lippert P. Antimicrobial and tumor-inhibiting properties of dithiourethane and studies on the mechanism of action. 16. Cytostatica. Pharmazie 1972;27:139–45
  • Martens T, Langevin-Bermond D, Fleury MB. Ditiocarb: decomposition in aqueous solution and effect of the volatile product on its pharmacological use. J Pharm Sci 1993;82:379–83
  • Valentine WM, Amarnath V, Amarnath K, et al. Carbon disulfide mediated protein cross-linking by N,N-diethyldithiocarbamate. Chem Res Toxicol 1995;8:96–102
  • Kumar KS, Sancho AM, Weiss JF. A novel interaction of diethyldithiocarbamate with the glutathione/glutathione peroxidase system. Int J Radiat Oncol Biol Phys 1986;12:1463–7
  • Hosni M, Meskini N, Prigent AF, et al. Diethyldithiocarbamate (ditiocarb sodium) effect on arachidonic acid metabolism in human mononuclear cells. Glutathione peroxidase-like activity. Biochem Pharmacol 1992;43:1319–29
  • Carta F, Aggarwal M, Maresca A, et al. Dithiocarbamates strongly inhibit carbonic anhydrases and show antiglaucoma action in vivo. J Med Chem 2012;55:1721–30
  • Carta F, Aggarwal M, Maresca A, et al. Dithiocarbamates: a new class of carbonic anhydrase inhibitors. Crystallographic and kinetic investigations. Chem Commun 2012;48:1868–70
  • Junior CV, Danuello A, Bolzani VDS, et al. Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 2007;14:1829–52
  • Gediya LK, Njar VC. Promise and challenges in drug discovery and development of hybrid anticancer drugs. Expert Opin Drug Discov 2009;4:1099–111
  • Barta TE, Barabasz AF, Foley BE, et al. Novel carbazole and acyl-indole antimitotics. Bioorg Med Chem Lett 2009;19:3078–80
  • Chen J, Lou J, Liu T, et al. Synthesis and in-vitro antitumor activities of some Mannich bases of 9-alkyl-1,2,3,4-tetrahydrocarbazole-1-ones. Arch Pharm Chem Life Sci 2009;342:165–72
  • Shmeiss NAMM, Ismail MMF, Soliman AM, El-Diwani HI. Synthesis of novel 1-substituted and 1,9-disubstituted-1,2,3,4-tetrahydro-9H-carbazole derivatives as potential anticancer agents. Molecules 2000;5:1101–12
  • Vas A, Gulyás B. Eburnamine derivatives and the brain. Med Res Rev 2005;25:737–57
  • Ishikawa H, Colby DA, Seto S, et al. Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues. J Am Chem Soc 2009;131:4904–16
  • Roepke J, Salim V, Wu M, et al. Vinca drug components accumulate exclusively in leaf exudates of Madagascar periwinkle. Proc Natl Acad Sci USA 2010;107:15287–92
  • Woods JR, Riofski MV, Zheng MM, et al. Synthesis of 15-methylene-eburnamonine from (+)-vincamine, evaluation of anticancer activity, and investigation of mechanism of action by quantitative NMR. Bioorg Med Chem Lett 2013;23:5865–9
  • Lake RJ, Blunt JW, Munro MHG. Eudistomins from the New Zealand Ascidian Ritterella sigillinoides. Aust J Chem 1989;42:1201–6
  • Kumar D, Rawat DS. Marine natural alkaloids as anticancer agents. In: Opportunity, challenge and scope of natural products in medicinal chemistry; 2011:213–68
  • Ettel V, Myska J. New derivatives of tetrahydrocarbazole and hexahydrocarbazole. Chem List 1955;49:1667–70
  • Altıntop MD, Gurkan-Alp AS, Özkay Y, Kaplancıklı ZA. Synthesis and biological evaluation of a series of dithiocarbamates as new cholinesterase inhibitors. Arch Pharm Chem Life Sci 2013;346:1–6
  • Furniss BS, Hannaford AJ, Smith PWG, Tautchell AR. Aliphatic compounds: aliphatic sulphur compounds. In: Vogel's textbook of practical organic chemistry. 5th ed. London, UK: Longman Scientific & Technical; 1989:792–3
  • Ozdemir A, Turan-zitouni G, Kaplancikli ZA. Novel analogues of 2-pyrazoline: synthesis, characterization, and antimycobacterial evaluation. Turk J Chem 2008;32:529–38
  • Kemp W. Organic spectroscopy. 3rd ed. London, UK: The Macmillan Press Ltd; 1991
  • Skehan P, Storeng R, Scudiero D, et al. New colorimetric assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107–12
  • Furniss BS, Hannaford AJ, Smith PWG, Tautchell AR. Selected heterocyclic compounds. In: Vogel's textbook of practical organic chemistry. 5th ed. London, UK: Longman Scientific & Technical; 1989:1161–2

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