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Research Article

Synthesis, cytotoxic, anti-lipoxygenase and anti-acetylcholinesterase capacities of novel derivatives from harmine

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Pages 23-33 | Received 11 Nov 2015, Accepted 02 Mar 2016, Published online: 30 Mar 2016

References

  • Borde V, Sonwane B, Sontakke V, Somwanshi B. Isolation and purification of alkaloids from medicinal plants by HPLC. Int J Curr Microbiol App Sci 2014;3:414–23
  • Bhat SV, Nagasampagi BA, Sivakumar M. Chemistry of natural products. New Delhi, India: Narosa; 2005:4–237
  • Dewick PM. Medicinal natural products: a biosynthetic approach. England: John Wiley & Sons Ltd; 2002:6–291
  • Colace C. Drug dreams in mescaline and LSD Addiction. Am J Addict 2010;19:192
  • Guilbaud N, Léonce S, Tillequin F, et al. Acronycine derivatives as promising antitumor agents. Anticancer Drugs 2002;13:445–9
  • Bechtold T, Mahmud-Ali A, Mussak R. Natural dyes for textile dyeing: a comparison of methods to assess the quality of Canadian golden rod plant material. Dyes Pigm 2007;75:287–93
  • Küpeli E, Koşar M, Yeşilada E, et al. A comparative study on the anti-inflammatory, antinociceptive and antipyretic effects of isoquinoline alkaloids from the roots of Turkish Berberis species. Life Sci 2002;72:645–57
  • Tiong SH, Looi CY, Hazni H, et al. Antidiabetic and antioxidant properties of alkaloids from Catharanthus roseus (L.) G. Don. Molecules 2013;18:9770–84
  • Jiménez J, Riverón-Negrete L, Abdullaev F, et al. Cytotoxicity of the beta-carboline alkaloids harmine and harmaline in human cell assays in vitro. Exp Toxicol Pathol 2008;60:381–9
  • Zhao T, Wang CH, Wang ZT. Chemical constituents and pharmacologic actions of genus Peganum: research advances. J Internat Pharmaceut Res 2010;37:333–9
  • Zeng Y, Zhang Y, Weng Q, et al. Cytotoxic and insecticidal activities of derivatives of harmine, a natural insecticidal component isolated from Peganum harmala. Molecules 2010;15:7775–91
  • Filali I, Bouajila J, Znati M, et al. Synthesis of new isoxazoline derivatives from harmine and evaluation of their anti-Alzheimer, anti-cancer and anti-inflammatory activities. J Enzyme Inhib Med Chem 2015;30:371–6
  • Frédérick R, Bruyère C, Vancraeynest C, et al. Novel trisubstituted harmine derivatives with original in vitro, anticancer activity. J Med Chem 2012;55:6489–501
  • Agbalyan SG. Cyanoethylation of harmine and tetrahydroharmine. Izvestiya Akademii Nauk Armyanskoi SSR, Khimicheskie Nauki 1961;14:611–6
  • Lee YS, Kim BH. Heterocyclic nucleoside analogues: design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles. Bioorg Med Chem Lett 2002;12:1395–402
  • Cao R, Chen H, Peng W, et al. Design, synthesis and in vitro and in vivo antitumor activities of novel beta-carboline derivatives. Eur J Med Chem 2005;40:991–1001
  • Meinguet C, Bruyère C, Frédérick R, et al. 3D-QSAR, design, synthesis and characterization of trisubstituted harmine derivatives with in vitro antiproliferative properties. Eur J Med Chem 2015;94:45–55
  • Katritzky AR, Wang M, Zhang S. One-pot synthesis of cinnamoyl hydrazides. Arkivoc 2001;2001:19–23
  • Abdel-Aziz HA, Elsaman T, Attia MI, Alanazi AM. The reaction of ethyl 2-oxo-2H-chromene-3-carboxylate with hydrazine hydrate. Molecules 2013;18:2084–95
  • Abdel-Aziz M, Abuo-Rahma GEA, Hassan AA. Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur J Med Chem 2009;44:80–7
  • Mamolo MG, Falagiani V, Zampieri D, et al. Synthesis and antimycobacterial activity of (3,4-diaryl-3H-thiazol-2-ylidene)-hydrazide derivatives. IL Farmaco 2003;58:631–7
  • Jha KK, Samad A, Kumar Y, et al. Design, synthesis and biological evaluation of 1,3,4-oxadiazole derivatives. Eur J Med Chem 2010;45:4963–7
  • Almajan GL, Barbuceanu SF, Bancescu G, et al. Synthesis and antimicrobial evaluation of some fused heterocyclic [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives. Eur J Med Chem 2010;45:6139–46
  • Kasimogullari BO, Cesur Z. Fused heterocycles: synthesis of some new imidazo[1,2-a]-pyridine derivatives. Molecules 2004;9:894–901
  • Attanasi OA, Filippone P, Perrulli FR, Santeusanio S. Regioselective role of the hydrazide moiety in the formation of complex pyrrole-pyrazole systems. Tetrahedron 2001;57:1387–94
  • Asif M, Husain A. Analgesic, anti-Inflammatory and antiplatelet profile of hydrazones containing synthetic molecules. J Appl Chem 2013;2013:1–7
  • Sztanke K, Tuzimski T, Rzymowska J, et al. Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives. Eur J Med Chem 2008;43:404–19
  • Salgin GU, Gokham KN, Gostal O, et al. 1-Acylthiose-micarbazides,1,2,4-triazole-5(4H)-thiones,1,3,4-thia-diazoles and hydrazones containing 5-methyl-2-benzo-xazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg Med Chem 2007;15:5738–51
  • Govindasami T, Pandey A, Palanivelu N, Pandey A. Synthesis, characterization and antibacterial activity of biologically important vanillin related hydrazone derivatives. Int J Org Chem 2011;1:71–7
  • Özçelik AB, Gökçe M, Orhan I, Şahin MF. Synthesis and acetylcholinesterase/butyrylcholinesterase inhibitory activities of (substituted/nonsubstituted benzal) hydrazone derivatives of 3-(6-substituted-3(2H)-pyridazinon-2yl)propionohydrazides. J Pharm Sci 2010;35:153–61
  • Singh M, Raghav N. Biological activities of hyrazones: a review. Int J Pharm Pharm Sci 2011;3:26–32
  • Chen M, Lu S, Yuag G, et al. Synthesis and antibacterial activity of some heterocyclic β-enamino ester derivatives with 1,2,3-triazole. Heterocyclic Comm 2000;6:421–6
  • Banu KM, Dinakar A, Anantharayanan C. Synthesis, characterization, antimicrobial studies and pharmacological screening of some substituted 1,2,3-triazoles. Indian J Pharm Sci 1999;4:202–5
  • Huisgen R. 1,3-Dipolar cycloaddition. Angew Chem Int Ed 1963;2:565–98
  • Kolb HC, Finn MG, Sharpless KB. Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed Engl 2001;40:2004–21
  • Woźnica M, Butkiewicz A, Grzywacz A, et al. Ring-expanded bicyclic β-lactams: a structure-chiroptical properties relationship investigation by experiment and calculations. J Org Chem 2011;76:3306–19
  • Özdemir A, Turan-Zitouni G, Kaplancikli ZA, Altintop MD. The synthesis of some new hydrazone derivative containing the benzothiazole moiety. J Serb Chem Soc 2012;77:141–6
  • Katrusiak A, Katrusiak A. One-step ring condensation of hydrazine derivatives and cyclic anhydrides. J Mol Struct 2015;1085:28–36
  • Filali I, Romdhane A, Znati M, et al. Synthesis of new harmine isoxazoles and evaluation of their potential anti-Alzheimer, anti-inflammatory and anticancer activities. Med Chem 2016;12:184–90
  • Pellissier H. Asymmetric 1,3-dipolar cycloadditions. Tetrahedron 2007;63:3235–85
  • Liyuan L, Didier A. The copper(I)-catalyzed alkyne-azidecycloaddition (CuAAC) “click” reaction and its applications. Coord Chem Rev 2011;255:2933–45
  • Bendaoud H, Romdhane M, Souchard JP, et al. Chemical composition and anticancer and antioxidant activities of Schinus molle L. and Schinus terebinthifolius addi berries essential oils. J Food Sci 2010;75:466–72
  • Khlifi D, Sghaier RM, Amouri S, et al. Composition and anti-oxidant, anti-cancer and anti-inflammatory activities of Artemisia herba-alba, Ruta chalpensis L. and Peganum harmala L. Food Chem Toxicol 2013;55:202–8
  • Bekir J, Mars M, Souchard JP, Bouajila J. Assessment of anti-oxidant, anti-inflammatory, anti-cholinesterase and cytotoxic activities of pomegranate (Punica granatum) leaves. Food Chem Toxicol 2013;55:470–5
  • Kaplancikli ZA, Altintop MD, Ozdemir A, et al. Synthesis and biological evaluation of some hydrazone derivatives as anti-inflammatory agents. Lett Drug Des Discov 2012;9:310–5
  • Kumar HSN, Parumasivam T, Jumaat F, et al. Synthesis and evaluation of isonicotinoylhydrazone derivatives as antimycobacterial and anticancer agents. Med Chem Res 2014;23:269–79
  • Cuadro AM, Valenciano J, Vaquero JJ, et al. Synthesis and biological evaluation of 2,6-di-tert-butylphenol hydrazones as 5-lipoxygenase inhibitors. Bioorg Med Chem 1998;6:173–80

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