Naphthalimide derivatives with therapeutic characteristics: a patent review

Bibliography

• Brana M, Castellano J, Moran M, Synthesis, structure and anti-tumor activity of new benz [d, e] isoquinoline-1, 3-diones. Arzneimittelforschung 1995;45:1311-18
   PubMedGoogle Scholar
• Bailly C, Carrasco C, Joubert A, Chromophore-modified bisnaphthalimides: DNA recognition, topoisomerase inhibition, and cytotoxic properties of two mono-and bisfuronaphthalimides. Biochemistry 2003;42:4136-50
   PubMedGoogle Scholar
• Li X, Lin Y, Wang Q, The novel anti-tumor agents of 4-triazol-1, 8-naphthalimides: synthesis, cytotoxicity, DNA intercalation and photocleavage. Eur J Med Chem 2011;46:1274-9
   PubMed Web of Science ®Google Scholar
• Kamal A, Reddy B, Reddy G, Design and synthesis of C-8 linked pyrrolobenzodiazepine-naphthalimide hybrids as anti-tumour agents. Bioorg Med Chem Lett 2002;12:1933-5
   PubMed Web of Science ®Google Scholar
• Filosa R, Peduto A, Micco SD, Molecular modelling studies, synthesis and biological activity of a series of novel bisnaphthalimides and their development as new DNA topoisomerase II inhibitors. Bioorg Med Chem 2009;17:13-24
   PubMed Web of Science ®Google Scholar
• Muth M, Hoerr V, Glaser M, Anti-trypanosomal activity of quaternary naphthalimide derivatives. Bioorg Med Chem Lett 2007;17:1590-3
   PubMed Web of Science ®Google Scholar
• Chang SC, Archer BJ, Utecht RE, 4-Alkylamino-3-bromo-N-alkyl-1, 8-naphthalimides: new photochemically activatable anti-viral compounds. Bioorg Med Chem Lett 1993;3:555-6
   Web of Science ®Google Scholar
• Chanh TC, Lewis DE, Judy MM, Inhibition of retrovirus-induced syncytium formation by photoproducts of a brominated 1, 8-naphthalimide compound. Antiviral Res 1994;25:133-46
   PubMedGoogle Scholar
• da Settimo A, Primofiore G, Ferrarini PL, Reinvestigation of reductive butylation of aminophthalimides: new compounds with local anesthetic activity. Eur J Med Chem 1989;24:263-70
   Google Scholar
• Andricopulo AD, Muller LA, Cechinel Filho V, Analgesic activity of cyclic imides: 1, 8-naphthalimide and 1, 4, 5, 8-naphthalenediimide derivatives. Il Farmaco 2000;55:319-21
   PubMedGoogle Scholar
• Clark R, Weinhardt K, Berger J, N-(quinuclidin-3-YL)-1, 8,-naphthalimides with 5-HT3 receptor antagonist and 5-HT4 receptor agonist properties. Bioorg Med Chem Lett 1993;3:1375-8
   Web of Science ®Google Scholar
• Berque-Bestel I, Soulier JL, Giner M, Synthesis and characterization of the first fluorescent antagonists for human 5-HT4 receptors. J Med Chem 2003;46:2606-20
   PubMed Web of Science ®Google Scholar
• Duke RM, Veale EB, Pfeffer FM, Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1, 8-naphthalimide-based chemosensors. Chem Soc Rev 2010;39:3936-53
   PubMed Web of Science ®Google Scholar
• Dorlars A, Schellhammer CW, Schroeder J. Heterocycles as structural units in new optical brighteners. Angew Chem Int Ed Engl 1975;14:665-79
   Web of Science ®Google Scholar
• Wolfbeis OS. Materials for fluorescence-based optical chemical sensors. J Mater Chem 2005;15:2657-69
   Web of Science ®Google Scholar
• Xu Z, Yoon J, Spring DR. A selective and ratiometric Cu2+ fluorescent probe based on naphthalimide excimer–monomer switching. Chem Commun 2010;46:2563-5
   PubMed Web of Science ®Google Scholar
• Xu Z, Qian X, Cui J. Colorimetric and ratiometric fluorescent chemosensor with a large red-shift in emission: Cu (II)-only sensing by deprotonation of secondary amines as receptor conjugated to naphthalimide fluorophore. Org Lett 2005;7:3029-32
   PubMed Web of Science ®Google Scholar
• Stewart WW. Functional connections between cells as revealed by dye-coupling with a highly fluorescent naphthalimide tracer. Cell 1978;14:741-59
   PubMed Web of Science ®Google Scholar
• Ingrassia L, Lefranc F, Kiss R, Naphthalimides and azonafides as promising anticancer agents. Curr Med Chem 2009;16:1192-213
   PubMed Web of Science ®Google Scholar
• Lv M, Xu H. Overview of naphthalimide analogs as anticancer agents. Curr Med Chem 2009;16:4797-813
   PubMed Web of Science ®Google Scholar
• Stevenson KA, Yen SF, Yang NC, A substituent constant analysis of the interaction of substituted naphthalene monoimides with DNA. J Med Chem 1984;27(12):1677-82
   PubMedGoogle Scholar
• Brana M, Ramos A. Naphthalimides as anticancer agents: synthesis and biological activity. Curr Med Chem Anticancer Agents 2001;1:237-55
   PubMedGoogle Scholar
• Heron M, Hoyert DL, Murphy SL, National vital statistics reports. Nat Vit Stat Rep 2009;57:1–136.
   PubMedGoogle Scholar
• Hurley LH. DNA and its associated processes as targets for cancer therapy. Nat Rev Cancer 2002;2:188-200
   PubMed Web of Science ®Google Scholar
• Helleday T, Petermann E, Lundin C, DNA repair pathways as targets for cancer therapy. Nat Rev Cancer 2008;8:193-204
   PubMed Web of Science ®Google Scholar
• Arcamone FM, Animati F, Barbieri B, Synthesis, DNA-binding properties, and anti-tumor activity of novel distamycin derivatives. J Med Chem 1989;32:774-8
   PubMed Web of Science ®Google Scholar
• Brana MF, Cacho M, Garcia MA, New analogues of amonafide and elinafide, containing aromatic heterocycles: synthesis, anti-tumor activity, molecular modeling, and DNA binding properties. J Med Chem 2004;47:1391-9
   PubMedGoogle Scholar
• Zee-Cheng RKY, Cheng C. N-(Aminoalkyl) imide anti-neoplastic agents. Synthesis and biological activity. J Med Chem 1985;28:1216-22
   PubMed Web of Science ®Google Scholar
• Chen Z, Liang X, Zhang H, A new class of naphthalimide-based anti-tumor agents that inhibit topoisomerase II and induce lysosomal membrane permeabilization and apoptosis. J Med Chem 2010;53:2589-600
   PubMed Web of Science ®Google Scholar
• Xie L, Cui J, Qian X, 5-Non-amino aromatic substituted naphthalimides as potential anti-tumor agents: synthesis via suzuki reaction, anti-proliferative activity, and DNA-binding behavior. Bioorg Med Chem 2011;19:961-7
   PubMedGoogle Scholar
• Li X, Lin Y, Yuan Y, Novel efficient anticancer agents and DNA intercalators of 1, 2, 3-triazol-1, 8-naphthalimides: design, synthesis and biological activity. Tetrahedron 2011;67:2299-304
   Web of Science ®Google Scholar
• Yin H, Zhu W, Xu Y, Novel aliphatic N-oxide of naphthalimides as fluorescent markers for hypoxic cells in solid tumor. Eur J Med Chem 2011;46:3030-7
   PubMedGoogle Scholar
• Azeeza S, Bharathi E, Malik M, Search for new and novel chemotherapeutics for the treatment of human malignancies. Mini Rev Med Chem 2010;10:405-35
   PubMedGoogle Scholar
• Yen SF, Gabbay EJ, Wilson WD. Interaction of aromatic imides with DNA. 1. Spectrophotometric and viscometric studies. Biochemistry 1982;21:2070-6
   PubMed Web of Science ®Google Scholar
• Kamal A, Adil S, Tamboli JR, Synthesis and anticancer activity of phthalimido and naphthalimido substituted dihydropyrimidone conjugates. Lett Drug Des Discov 2008;5:261-70
   Google Scholar
• Kamal A, Adil S, Tamboli JR, Synthesis of coumarin linked naphthalimide conjugates as potential anticancer and anti-microbial agents. Lett Drug Des Discov 2009;6:201-9
   Google Scholar
• Kamal A. Novel naphthalimide-benzimidazole hybrids as potential anti-tumour agents and process for the preparation thereof. WO2009110000; 2009
   Google Scholar
• Tumiatti V, Milelli A, Minarini A, Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞. J Med Chem 2009;52:7873-7
   PubMed Web of Science ®Google Scholar
• Van Quaquebeke E, Mahieu T, Dumont P, 2, 2, 2-trichloro-N-({2-[2-(dimethylamino) ethyl]-1, 3-dioxo-2, 3-dihydro-1 H-benzo [de] isoquinolin-5-yl} carbamoyl) acetamide (UNBS3157), a novel nonhematotoxic naphthalimide derivative with potent anti-tumor activity. J Med Chem 2007;50:4122-34
   PubMed Web of Science ®Google Scholar
• Perez JM, Lopez-Solera I, Montero EI, Combined effect of platination and intercalation upon DNA binding of novel cytotoxic Pt-bis (naphthalimide) complexes. J Med Chem 1999;42:5482-6
   PubMed Web of Science ®Google Scholar
• Ott I, Qian X, Xu Y, A gold (I) phosphine complex containing a naphthalimide ligand functions as a TrxR inhibiting anti-proliferative agent and angiogenesis inhibitor. J Med Chem 2009;52:763-70
   PubMed Web of Science ®Google Scholar
• Peduto A, Pagano B, Petronzi C, Design, synthesis, biophysical and biological studies of trisubstituted naphthalimides as G-quadruplex ligands. Bioorg Med Chem 2011;19:6419-29
   PubMedGoogle Scholar
• Wang K, Wang Y, Yan X, DNA binding and anticancer activity of naphthalimides with 4-hydroxyl-alkylamine side chains at different lengths. Bioorg Med Chem Lett 2012;22:937-41
   PubMedGoogle Scholar
• Zhao L, Li J, Li Y, Selenium-containing naphthalimides as anticancer agents: design, synthesis and bioactivity. Bioorg Med Chem 2012;20:2558-63
   PubMed Web of Science ®Google Scholar
• Xie S, Zhang Y, Li Q, 3-Nitro-naphthalimide and nitrogen mustard conjugate NNM-25 induces hepatocellular carcinoma apoptosis via PARP-1/p53 pathway. Apoptosis 2012;17:725-37
   PubMedGoogle Scholar
• Mohammadkhodaei Z, Mokhtari J, Nouri M. Novel anti-bacterial acid dyes derived from naphthalimide: synthesis, characterisation and evaluation of their technical properties on nylon 6. Color Tech 2010;126:81-5
   Google Scholar
• Tischer M, Sologub L, Pradel G, The bisnaphthalimides as new active lead compounds against Plasmodium falciparum. Bioorg Med Chem 2010;18:2998-03
   PubMed Web of Science ®Google Scholar
• Zhang Y, Feng S, Wu Q, Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers. Med Chem Res 2011;20:752-9
   Web of Science ®Google Scholar
• Mata MA, Satterly N, Versteeg GA, Chemical inhibition of RNA viruses reveals REDD1 as a host defense factor. Nat Chem Biol 2011;7:712-19
   PubMed Web of Science ®Google Scholar
• Kamal A, Rondla R, Khanna G, Pyrrolo [2, 1-c][1, 4] benzodiazepine-napthalimide conjugates linked through piperazine moiety and process for preparation thereof. WO2006003670; 2006
   Google Scholar
• Kamal A, Ramu R, Tekumalla V, Preparation of pyrrolo[2,1-c][1,4]benzodiazepine-aphthalimide conjugates linked through piperazine moiety useful as antitumor agents. IN2004DE01218; 2004
   Google Scholar
• Gazzard L. Heterocyclic-substituted bis-1, 8 naphthalimide compounds, antibody drug conjugates, and methods of use. WO2007064345; 2007
   Google Scholar
• Ferri N, Radice T, Antonino M, Synthesis, structural and biological evaluation of bis-heteroarylmaleimides and bis-heterofused imides. Bioorg Med Chem 2011;19:5291-9
   PubMed Web of Science ®Google Scholar
• Lahav R, Patterson PH. Compositions and methods for treating cancer using compositions comprising an inhibitor of endothelin receptor activity. US20060094676; 2006
   Google Scholar
• Hellstrand K, Hermodsson S, Thoren F, Use of PARP-1 inhibitors for protecting tumorcidal lymphocytes from apoptosis. WO2006039545; 2006
   Google Scholar
• Hellstrand K, Hermodsson S, Thoren F, Use of PARP-1 inhibitors for protecting tumorcidal lymphocytes from apoptosis. US20060079510; 2006
   Google Scholar
• Scotto KA, Mandola M. Use of PARP-1 inhibitors. WO2007062413; 2007
   Google Scholar
• Biro A, Katzir Z. Combination of an Aminoglycoside Antibiotic and a PARP. Inhibitor. WO2008050339; 2008
   Google Scholar
• Kerr DA, Kaplin AI, Krishnan C. Use of IL-6 in the diagnosis and treatment of neuroinflammatory conditions. WO2008016707; 2008
   Google Scholar
• Brownlee M. Use of PARP inhibitors for prevention and treatment of diabetic and insulin resistance complications. US20080161255; 2008
   Google Scholar
• Krawczyk P, Aten JA, Kanaar R, Method of treating cancer. WO2010082821; 2010
   Google Scholar
• Chowdhury D. Mir-182 in the diagnosis and treatment of cancer. US20110178163; 2011
   Google Scholar
• O'malley BW, Abuzeid WM, Li D. Anti-neoplastic combination therapy comprising co-disruption pathway and mre11/rad50/nbs1 complex and compositon thereof. WO2009114459; 2009
   Google Scholar
• Carroll S, Hernando JIM, Malancona S, Naphthalimide derivatives as antiviral agents. WO2006027628; 2006
   Google Scholar
• Gopalsamy A, Lim K, Ellingboe JW, Identification of [(naphthalene-1-carbonyl)-amino]-acetic acid derivatives as nonnucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase. Bioorg Med Chem Lett 2004;14:4221-4
   PubMedGoogle Scholar
• Levenson JM, Sweatt JD. Histone deacetylase inhibitors and cognitive applications. US20060018921; 2006
   Google Scholar
• Kim HJ, Rowe M, Ren M, Histone deacetylase inhibitors exhibit anti-inflammatory and neuroprotective effects in a rat permanent ischemic model of stroke: multiple mechanisms of action. J Pharmacol Exp Ther 2007;321:892-901
   PubMed Web of Science ®Google Scholar
• Zuo T, Liu R, Zhang H, FOXP3 is a novel transcriptional repressor for the breast cancer oncogene SKP2. J Clin Invest 2007;117:3765
   PubMed Web of Science ®Google Scholar
• Gruber PJ, Epstein JA. Use of HDAC and/or DNMT inhibitors for treatment of ischemic injury. WO2006060382; 2006
   Google Scholar
• De la porte S, Israel M, Voisin V, Use of a histone deacetylase inhibitor for treating muscular dystrophies. US20060148684; 2006
   Google Scholar
• Bunn P, Witta S. Methods of using saha and erlotinib for treating cancer. WO2007056244; 2007
   Google Scholar
• Wang B. Compositions and methods for modulation of suppressor T cell activation. WO2007084775; 2007
   Google Scholar
• Palladino M. A method of using proteasome inhibitors in combination with histone deacetylase inhibitors to treat cancer. WO2008124699; 2008
   Google Scholar
• Ordentlich P, Horobin J. Combination of er alpha+ ligands and histone deacetylase inhibitors for the treatment of cancer. WO2008058287; 2008
   Google Scholar
• Steinbrecher A, Reinhold D, Quigley L, Targeting dipeptidyl peptidase IV (CD26) suppresses autoimmune encephalomyelitis and up-regulates TGF-beta1 secretion in vivo. J Immunol 2001;166:2041
   PubMedGoogle Scholar
• Ansorge S, Bank U, Nordhoff K, Novel alanyl-amino peptidase inhibitors for functionally influencing different cells and treating immunological, inflammatory, neuronal, and other diseases. US20070037752; 2007
   Google Scholar
• Plato C. Combinations comprising a histone deacetylase inhibiting agent and a nuclear hormone receptor ligand for treating cardiovascular conditions. WO2007100795; 2007
   Google Scholar
• Leonard TW. Solid oral dosage form containing an enhancer. US20070292512; 2007
   Google Scholar
• Kushner P, Goldfine ID, Hodges-gallagher L, Small molecule potentiator of hormonal therapy for breast cancer. WO2008027837; 2008
   Google Scholar
• Atadja PW, Bhalla KN, Manley PW. Combination of organic compounds. US20080200489; 2008
   Google Scholar
• Pandey SC. Histone acetyle transferase activators and histone deacetylase inhibitors in the treatment of alcoholism. WO2008042795; 2008
   Google Scholar
• Van Quaquebeke E, Simon G, Van den hove L, Napthalimide derivatives, methods for their production and pharmaceutical compositions therefrom. US20070117836; 2007
   Google Scholar
• Van quaquebeke E, Simon G, El yazidi M, 5-Urea substituted naphthalimide derivatives, methods of production and pharmaceutical compositions for treating cancer. WO2007128538; 2007
   Google Scholar
• Van Quaquebeke E, Simon G, El Yazidi M, Compositions and methods for treatment of prostate and breast cancer. US20090221628; 2009
   Google Scholar
• Van Quaquebeke E, Simon G, El Yazidi M, Compositions and methods for treatment of esophageal cancer. US20090232907; 2009
   Google Scholar
• Brown DM. Naphthalimide compositions and uses thereof. US20070207977; 2007
   Google Scholar
• Brown DM. Naphthalimide compositions and uses thereof. US20060211648; 2006
   Google Scholar
• McCulloch W, Keegan M. Gemcitabine combination therapy. WO2007145704; 2007
   Google Scholar
• McCulloch W. Deacetylase inhibitor therapy. WO2007146730; 2007
   Google Scholar
• Lange N. Compounds for photochemotherapy. WO2007023398; 2007
   Google Scholar
• Qazi GN, Saxena AK, Muthiah S, Novel substituted 1H-benz [de] isoquinoline-1, 3-diones. WO2008084496; 2008
   Google Scholar
• Imperiali B, Loving GS. Environmentally sensitive fluorophores. US20080206885; 2008
   Google Scholar
• Vohra R, Dube G, Gan Z, Methods of modulating neurotrophin-mediated activity. US20090082368; 2009
   Google Scholar
• Huang S, Norton J, Appella D, Anticancer compounds. WO2009089537; 2009
   Google Scholar
• Wang W, Cheng W, Yang J. Method of inhibiting the growth of Helicobacter pylori. US20100305152; 2010
   Google Scholar