Synthesis of new isoxazoline derivatives from harmine and evaluation of their anti-Alzheimer, anti-cancer and anti-inflammatory activities

References

• Fan G, Li Z, Shen S, et al. Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera. Bioorg Med Chem 2010;18:5466–74
   PubMed Web of Science ®Google Scholar
• Bouayad N, Rharrabe K, Lamhamdi M, et al. Dietary effects of harmine, a β-carboline alkaloid, on development, energy reserves and a amylase activity of Plodia interpunctella Hübner [Lepidoptera: Pyralidae]. Saudi J Biol Sci 2011;19:73–80
   Web of Science ®Google Scholar
• Pandurangan A, Khosa RL, Hemalatha S. Anti-inflammatory activity of an alkaloid from Solanum trilobatum on acute and chronic inflammation models. Nat Prod Res 2011;25:1132–41
   PubMed Web of Science ®Google Scholar
• Rohan AD, Sandra D, Sabine F, et al. Thiaplakortones A–D: antimalarial thiazine alkaloids from the Australian marine sponge Plakortis lita. J Org Chem 2013;78:9608–961
   PubMed Web of Science ®Google Scholar
• Soon HT, Chung YL, Hazrina H, et al. Antidiabetic and antioxidant properties of alkaloids from Catharanthus roseus (L.) G. Don Molecules 2013;18:9770–84
   PubMed Web of Science ®Google Scholar
• Kumar D, Rawat DS. Marine natural alkaloids as anticancer agents. Opport Chall Scope Nat Prod Med Chem 2011:213–68
   Google Scholar
• Rihui C, Wenlie P, Zihou W, Anlong X. Carboline alkaloids: biochemical and pharmacological functions. Curr Med Chem 2007;14:479–500
   PubMed Web of Science ®Google Scholar
• Cao R, Peng W, Wang Z, Xu A. beta-Carboline alkaloids: biochemical and pharmacological functions. Curr Med Chem 2007;14:479–500
   PubMed Web of Science ®Google Scholar
• Bouayad N, Rharrabe K, Lamhamdi M, et al. Dietary effects of harmine, a β-carboline alkaloid, on development, energy reserves and a amylase activity of Plodia interpunctella Hübner [Lepidoptera: Pyralidae]. Saudi J Biolog Sci 2011;19:73–80
   Web of Science ®Google Scholar
• Cao R, Yi W, Wu Q, et al. Synthesis and cytotoxic activities of 1-benzylidine substituted beta-carboline derivatives. Bioorg Med Chem Lett 2008;18:6558–61
   PubMed Web of Science ®Google Scholar
• Rook Y, Schmidtke KU, Gaube F, et al. Bivalent beta-carbolines as potential multitarget anti-Alzheimer agents. J Med Chem 2010;53:3611–17
   PubMed Web of Science ®Google Scholar
• Judith J, Leticia RN, Fikrat A, et al. Cytotoxicity of the b-carboline alkaloids harmine and harmaline in human cell assays in vitro. Exp Toxicol Pathol 2008;60:381–9
   PubMed Web of Science ®Google Scholar
• Rahimi-Moghaddam P, Ebrahimi SA, Ourmazdi H, et al. In vitro and in vivo activities of Peganum harmala extract against Leishmania major. J Res Med Sci 2011;16:1032–9
   PubMed Web of Science ®Google Scholar
• Hun S, Xiaoli H, Yuanming Z, Chi Z. Main alkaloids of Peganum harmala L. and their different effects on dicot and monocot crops. Molecules 2013;1:2623–34
   Google Scholar
• Farouk L, Laroubi A, Aboufatima R, et al. Aninicociceptive activity of various extracts of Peganum harmala L. and possible mechanism of action. Iran J Pharmacol Therap 2009;8:29–35
   Google Scholar
• Goel N, Singh N, Saini R. Efficient in vitro multiplication of Syrian Rue (Peganum harmala L.) using 6-benzylaminopurine pre-conditioned seedling explants. Nature Sci 2009;7:1545–50
   Google Scholar
• Jinous A, Fereshteh R. Chemistry, pharmacology and medicinal properties of Peganum harmala L. Afr J Pharm Pharmacol 2012;6:1573–80
   Web of Science ®Google Scholar
• Nafisi S, Panahyab A, Sadeghi GB. Interactions between b-carboline alkaloids and bovine serum albumin: investigation by spectroscopic approach. J Luminesc 2012;132:2361–6
   Web of Science ®Google Scholar
• Cheng XM, Zhao T, Yang T, et al. HPLC fingerprints combined with principal component analysis, hierarchical cluster analysis and linear discriminant analysis for the classification and differentiation of Peganum sp. indigenous to China. Phytochem Anal 2010;21:279–89
   PubMed Web of Science ®Google Scholar
• Zhao T, Wang CH, Wang ZT. Chemical constituents and pharmacologic actions of genus Peganum: research advances. J Internat Pharmaceut Res 2010;37:333–45
   Google Scholar
• Milad M, Peyman M, Shahin A, et al. Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids. Pharmacogn Rev 2013;7:199–212
   Google Scholar
• Nafisi S, Bonsaii M, Maali P, et al. Beta-carboline alkaloids bind DNA. J Photochem Photobiol Biol 2010;100:84–91
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Patel K, Gadewar M, Tripathi R, et al. A review on medicinal importance, pharmacological activity and bioanalytical aspects of beta-carboline alkaloid “Harmine”. Asian Pacif J Trop Biomed 2012;2:660–4
   PubMedGoogle Scholar
• Lamchouri F, Toufik H, Elmalki Z, et al. Quantitative structure–activity relationship of antitumor and neurotoxic β-carbolines alkaloids: nine harmine derivatives. Res Chem Intermediat 2013;39:2219–36
   Web of Science ®Google Scholar
• Cao R, Guan X, Shi B, et al. Design, synthesis and 3D-QSAR of beta-carboline derivatives as potent antitumor agents. Eur J Med Chem 2010;45:2503–15
   PubMed Web of Science ®Google Scholar
• Fredérick R, Bruyère C, Vancraeynest C, et al. Novel trisubstituted harmine derivatives with original in vitro anticancer activity. J Med Chem 2012;55:6489–501
   PubMed Web of Science ®Google Scholar
• Jahaniani F, Ebrahimi SA, Rahbar-Roshandel N, Mahmoudian M. Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent. Phytochemistry 2005;66:1581–92
   PubMed Web of Science ®Google Scholar
• Lamchouri F, Toufik H, Bouzzine SM, et al. Experimental and computational study of biological activities of alkaloids isolated from Peganum harmala seeds J Mater Environ Sci 2010;1:343–52
   Google Scholar
• Berrougui H, López-Lázaro M, Martin-Cordero C, et al. Cytotoxic activity of methanolic extract and two alkaloids extracted from seeds of Peganum harmala. J Nat Remedies 2005;5:41–5
   Google Scholar
• Ma Y, Wink M. The beta-carboline alkaloid harmine inhibits BCRP and can reverse resistance to the anticancer drugs mitoxantrone and camptothecin in breast cancer cells. Phytother Res 2010;24:146–9
   PubMed Web of Science ®Google Scholar
• Frost D, Meechoovet B, Wang T, et al. β-Carboline compounds, including harmine, inhibit DYRK1A and tau phosphorylation at multiple Alzheimer's disease-related sites. PLoS One 2011;6:19264
   Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Stanisław K, Piotr B, Wojciech S. Convenient synthesis of isoxazolines via tandem isomerization of allyl compounds to vinylic derivatives and 1,3-dipolar cycloaddition of nitrile oxides to the vinylic compounds. Tetrahedron Lett 2008;49:6071–4
   Web of Science ®Google Scholar
• Sailu B, Srinivas M, Satya SA, et al. Synthesis and antibacterial activity of novel isoxazoline derivatives. Der Pharma Chemica 2012;4:2036–41
   Google Scholar
• Kai H, Matsumoto H, Hattori N, et al. Anti-influenza virus activities of 2-alkoxyimino-n-(2-isoxazolin-3-ylmethyl)acetamides. Bioorg Med Chem Lett 2001;11:1997–2000
   PubMed Web of Science ®Google Scholar
• Pirrung, MC, Tumey LN, Raetz CRH, et al. Inhibition of antibacterial target UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC). Isoxazoline zinc amidase inhibitors bearing diverse metal binding groups. J Med Chem 2002;45:4359–70
   PubMed Web of Science ®Google Scholar
• Maralinganadoddi PS, Basappa Shivananju NS, Feng L, et al. Anti-cancer activity of novel dibenzo[b,f]azepine tethered isoxazoline derivatives. BMC Chem Biol 2012;12:5
   PubMedGoogle Scholar
• Sureshbabu D, Adel N. Parallel synthesis of structurally diverse aminobenzimidazole tethered sultams and benzothiazepinones. Tetrahedron Lett 2012;53:2096–9
   PubMedGoogle Scholar
• Guilherme DV, Rafaela R da R, Paulo HS, et al. Expeditious preparation of isoxazoles from Δ2-isoxazolines as advanced intermediates for functional materials. Tetrahedron Lett 201;52:6569–72
   Google Scholar
• Shanmugavel UM, Subbu P. A facile sequential three-component regio- and stereoselective synthesis of novel spiro-isoxazoline/acridinone hybrids. Tetrahedron Lett 2012;53:6885–8
   Web of Science ®Google Scholar
• Kartal M, Altun ML, Kurucu S. HPLC method for the analysis of harmol, harmalol, harmine and harmaline in the seeds of Peganum harmala L. J Pharmaceut Biomed Anal 2003;31:263–9
   PubMed Web of Science ®Google Scholar
• Berrougui H, Martin-Cordero C, Khalil A, et al. Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta. Pharmacol Res 2006;54:150–7
   PubMed Web of Science ®Google Scholar
• Woznica 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
   PubMed Web of Science ®Google Scholar
• Pellissier H. Asymmetric 1,3-dipolar cycloadditions. Tetrahedron 2007;63:3235–85
   Web of Science ®Google Scholar
• Akkol EK, Orhan IE, Yeşilada E. Anticholinesterase and antioxidant effects of the ethanol extract, ethanol fractions and isolated flavonoids from Cistus laurifolius L. leaves. Food Chem 2012;131:626–31
   Web of Science ®Google Scholar
• Bendaoud H, Romdhane M, Souchard JP, et al. Chemical composition and anticancer and antioxidant activities of Schinus molle L. and Schinus terebinthifolius Raddi berries essential oils. J Food Sci 2010;75:466–72
   PubMed Web of Science ®Google Scholar
• Bylac S, Racine P. Inhibition of 5-lipoxygenase by essential oils and other natural fragrant extracts. Int J Aromather 2003;13:138–42
   Google Scholar
• Wang X, Geng Y, Wang D, et al. Separation and purification of harmine and harmaline from Peganum harmala using pH-zone-refining counter-current chromatography. J Sep Sci 2008;31:3543–47
   PubMed Web of Science ®Google Scholar
• Mata AT, Proenc C, Ferreira AR, et al. Antioxidant and antiacetylcholinesterase activities of five plants used as Portuguese fond spices. Food Chem 2007;103:778–86
   Web of Science ®Google Scholar
• Ting Z, Ke-min D, Lei Z, et al. Acetylcholinesterase and butyrylcholinesterase inhibitory activities of β-carboline and quinoline alkaloids derivatives from the plants of genus Peganum. J Chem 2013;17232(1–6)
   Google Scholar
• Albano SM, Lima AS, Miguel MG, et al. Antioxidant, anti-5-lipoxygenase and antiacetylcholinesterase activities of essential oils and decoction waters of some aromatic plants. Rec Nat Prod 2012;6:35–48
   Google Scholar