[1]
Kamal, A.; Bolla, N.R.; Srikanth, P.S.; Srivastava, A.K. Naphthalimide derivatives with therapeutic characteristics: A patent review. Expert Opin. Ther. Pat., 2013, 23(3), 299-317.
[2]
Banerjee, S.; Veale, E.B.; Phelan, C.M.; Murphy, S.A.
Tocci, G.M.; Gillespie, L.J.; Frimannsson, D.O.; Kelly, J.M.; Gunnlaugsson, T. Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents. Chem. Soc. Rev., 2013, 42, 1601-1618.
[3]
Wang, K-R.; Qian, F.; Wang, X-M.; Tan, G-H.; Rong, R-X.; Cao, Z-R.; Chen, H.; Zhang, P-Z.; Li, X-L. Cytotoxic activity and DNA binding of naphthalimide derivatives with amino acid and dichloroacetamide functionalizations. Chin. Chem. Lett., 2014, 25(7), 1087-1093.
[4]
Braña, M.F.; Ramos, A. Naphthalimides as anticancer agents: synthesis and biological activity. Anticancer. Agents Med. Chem., 2001, 1(3), 237-255.
[5]
Braña, M.F.; Sanz, A.M.; Castellano, J.M.; Roldán, C.M.; Roldán, C. Synthesis and cytostatic activity of benz(d.e)isoquinolin-1.3-diones. Structure-activity relationships. Eur. J. Med. Chem., 1981, 16, 207-212.
[6]
Braña, M.F.; Berlanga, J.M.C.; Roldan, C.M. 4-acylamino-nphenylbutyramides-
useful as pharmaceuticals. DE Patent 2,318,
136, November, 08, 1973.
[7]
Braña, M.F.; Castellano, J.M.; Roldán, C.M.; Santos, A.; Vázquez, D.; Jiménez, A. Synthesis and mode(s) of action of a new series of imide derivatives of 3-nitro-1,8 naphthalic acid. Cancer Chemother. Pharmacol., 1980, 4(1), 61-66.
[8]
Braña, M.F.; Castellano, J.M.; Jiménez, A.; Lombart, A.; Rabadan, F.P.; Roldán, M.; Roldán, C.; Santos, A.; Vázquez, D. Synthesis, cytostatic activity and mode of action of a new series of imide derivatives of 3-nitro-11α naphtalic acid. Curr. Chemother, 1978, 2, 1216-1217.
[9]
Waring, M.J.; Gonzalez, A.; Jimenez, A.; Vazquez, D. Intercalative binding to DNA of antitumour drugs derived from 3-nitro-1, 8-naphthalic acid. Nucleic Acids Res., 1979, 7(1), 217-230.
[10]
Hsiang, Y.H.; Jiang, J.B.; Liu, L.F. Topoisomerase II-mediated DNA cleavage by amonafide and its structural analogs. Mol. Pharmacol., 1989, 36(3), 371-376.
[11]
Wu, A.; Xu, Y.; Qian, X. Novel naphthalimide-amino acid conjugates with flexible leucine moiety as side chain: Design, synthesis and potential antitumor activity. Bioorg. Med. Chem., 2009, 17(2), 592-599.
[12]
Yang, Q.; Yang, P.; Qian, X.; Tong, L. Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity. Bioorg. Med. Chem. Lett., 2008, 18(23), 6210-6213.
[13]
Ramchander, J. Synthesis of 3 (N(1,3dioxo 1H benzo[de] isoquinolin-2(3H)-yl)alkyl)-2-(4-substituted) phenylthiazolidine-4-carboxylic acid. Der Pharma Chem., 2015, 7(11), 288-293.
[14]
Duke, R.M.; Veale, E.B.; Pfeffer, F.M.; Kruger, P.E.; Gunnlaugsson, T. Colorimetric and fluorescent anion sensors: An overview of recent developments in the use of 1,8-naphthalimide-based chemosensors. Chem. Soc. Rev., 2010, 39, 3936-3953.
[15]
Gunnlaugsson, T.; Glynn, M.; Tocci, G.M.; Kruger, P.E.; Pfeffer, F.M. Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors. Coord. Chem. Rev., 2006, 250(23-24), 3094-3117.
[16]
Li, Y.; Cao, L.; Tian, H. Fluoride ion-triggered dual fluorescence switch based on naphthalimides winged zinc porphyrin. J. Org. Chem., 2006, 71(21), 8279-8282.
[17]
Patrick, L.G.F.; Whiting, A. Synthesis and application of some polycondensable fluorescent dyes. Dyes Pigm, 2002, 52(2), 137-143.
[18]
Martin, E.; Weigand, R.; Pardo, A. Solvent dependence of the inhibition of intramolecular charge-transfer in N-substituted 1,8-naphthalimide derivatives as dye lasers. J. Lumin., 1996, 68(2-4), 157-164.
[19]
Tao, Z-F.; Qian, X. Naphthalimide hydroperoxides as photonucleases: Substituent effects and structural basis. Dyes Pigm., 1999, 43(2), 139-145.
[20]
Stewart, W.W. Synthesis of 3,6-disulfonated 4-aminonaphthalimides. J. Am. Chem. Soc., 1981, 103(25), 7615-7620.
[21]
Bouché, C-M.; Berdagué, P.; Facoetti, H.; Robin, P.; Barny, P.; Schott, M. Side-chain electroluminescent polymers. Synth. Met., 1996, 81(2-3), 191-195.
[22]
Tian, H.; Gan, J.; Chen, K.; He, J.; Song, Q.L.; Hou, X.Y. Positive and negative fluorescent imaging induced by naphthalimide polymers. J. Mater. Chem., 2002, 12, 1262-1267.
[23]
Zhu, W.; Hu, M.; Yao, R.; Tian, H. A novel family of twisted molecular luminescent materials containing carbazole unit for single-layer organic electroluminescent devices. Photochem. Photobiol. A: Chem, 2003, 154(2-3), 169-177.
[24]
Grabchev, I.; Chovelon, J-M. Synthesis and functional properties of green fluorescent poly(methylmethacrylate) for use in liquid crystal systems. Polym. Adv. Technol., 2003, 14, 601-608.
[25]
Cosnard, F.; Wintgens, V. A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide. Tetrahedron Lett., 1998, 39(18), 2751-2754.
[26]
De Souza, M.M.; Corrêa, R.; Cechinel, F.V.; Grabchev, I.; Bojinov, V. 4-Nitro-1,8-naphthalimides exhibit antinociceptive properties. Pharmazie, 2002, 57, 430-431.
[27]
Connors, T.A.; Elson, L.A.; Haddow, A.; Ross, W.C.J. The tumor growth inhibitory activity of 1-aminocyclopentanecarboxylic acid and related peptides. Biochem. Pharmacol., 1958, 1, 239-240.
[28]
Martel, F.; Berlinguet, L. Impairment of tumor growth by unnatural amino acids. Can. J. Biochem. Physiol., 1959, 37, 433-439.
[29]
Benefiel, W.W.; Helsper, J.T.; Sharp, G.S. Apparent control of multiple myeloma by 1-aminocyclopentane-1-carboxylic acid (NSC-1026). Cancer Chemother. Rep., 1960, 9, 21-22.
[30]
Goldin, A.; Vendditi, J.M.; Kline, I.; Mantel, N. Evaluation of antileukemic agents employing advanced Leukemia L-1210 in mice IV. Cancer Res., 1961, 21, 27-39.
[31]
Ross, R.B.; Noll, C.I.; Ross, W.C.J.; Nadkarni, M.V.; Morrison, B.H.; Bond, H.W. Cycloaliphatic amino acids in cancer chemotherapy. J. Med. Pharm. Chem., 1961, 3, 1-23.
[32]
Krant, M.J.; Iszard, D.M.; Abadi, A.; Carey, R.W. Treatment of multiple myeloma by 1-aminocyclopentanecarboxylic acid (NSC-1026). Cancer Chemother. Rep., 1962, 22, 59-64.
[33]
Hayes, R.L.; Washburn, L.C.; Wieland, B.W.; Sun, T.T.; Turtle, R.R.; Butler, T.A. Carboxy-labeled 11C-1-aminocyclopentanecarboxylic acid, a potential agent for cancer detection. J. Nucl. Med., 1976, 17, 748-751.
[34]
Staykova, S.T.; Wesselinova, D.W.; Vezenkov, L.T.; Naydenova, E.D. Synthesis and in vitro antitumor activity of new octapeptide analogs of somatostatin containing unnatural amino acids. Amino Acids, 2015, 47(5), 1007-1013.
[35]
Marinov, M.; Ganchev, D.; Nikolov, A.; Marinova, P.; Krustev, S.; Madzharova, V.; Stoyanov, N. In vitro fungicidal activity of cyclopentanespiro-5-hydantoin and its derivatives towards Blumeria graminis f. sp. tritici. Agric. Sci., 2013, 12, 97-101.
[36]
Marinov, M.N.; Ganchev, D.H.; Marinova, P.E.; Nikolov, A.S.; Prodanova, R.Y.; Krustev, S.V.; Zlateva, M.R.; Stoyanov, N.M. In vivo insecticidal activity of cyclopentanespiro-5-hydantoin and its two derivatives towards Oleander aphid (Aphis nerii) and effect on Buddleja davidii. J. Sci. Appl. Res, 2013, 4, 171-177.
[37]
Stoyanov, N.; Marinov, M. Two methods for spirothiohydantoin synthesis. Acta Chim. Slov., 2012, 59, 680-685.
[38]
Marinov, M.N.; Naydenova, E.D.; Prodanova, R.Y.; Stoyanov, N.M. Synthesis of some non-protein amino acids derived from spirohydantoins. J. Sci. Appl. Res, 2016, 10, 39-46.
[40]
Schmidt, M.W.; Baldridge, K.K.; Boatz, J.A.; Elbert, S.T.; Gordon, M.S.; Jensen, J.H.; Koseki, S.; Matsunaga, N.; Nguyen, K.A.; Su, S.; Windus, T.L.; Dupuis, M.; Montgomery, Jr, J.A. General atomic and molecular electronic structure system. J. Comput. Chem., 1993, 14(11), 1347-1363.
[41]
Gordon, M.S.; Schmidt, M.W. Advances in electronic structure theory: GAMESS a decade later.In: Theory and Applications of Computational Chemistry: The first forty years; Dykstra, C.E.; Frenking, G.; Kim, K.S.; Scuseria, G.E., Eds.; Elsevier, 2005, pp. 1167-1189.
[42]
Wolinski, K.; Hinton, J.F.; Pulay, P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc., 1990, 112, 8251-8260.
[43]
Ditchfield, R. Self-consistent perturbation theory of diamagnetism. Mol. Phys., 1974, 27, 789-807.
[44]
Tomasi, J.; Mennucci, B.; Cammi, R. Quantum mechanical continuum solvation models. Chem. Rev., 2005, 105(8), 2999-3093.
[45]
Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.P.; Izmaylov, A.F.; Bloino, J.; Zheng, G.; Sonnenberg, J.L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J.A., Jr; Peralta, J.E.; Ogliaro, F.; Bearpark, M.; Heyd, J.J.; Brothers, E.; Kudin, K.N.; Staroverov, V.N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J.C.; Iyengar, S.S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J.M.; Klene, M.; Knox, J.E.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Martin, R.L.; Morokuma, K.; Zakrzewski, V.G.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Dapprich, S.; Daniels, A.D.; Farkas, Ö.; Foresman, J.B.; Ortiz, J.V.; Cioslowski, J.; Fox, D.J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
[46]
Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods, 1983, 65(1-2), 55-63.
[47]
Konstantinov, S.; Eibl, M.H.; Berger, M.R. BCR-ABL influences the antileukemic efficacy of alkylphosphocholines. Br. J. Haematol., 1999, 107, 365-374.
[48]
Bucherer, H.T.; Lieb, V.A. On the formation of substituted hydantoins from aldehydes and ketones. Synthesis of hydantoins. J. Prakt. Chem., 1934, 141(1-2), 5-43.
[49]
Naydenova, E.; Pencheva, N.; Popova, J.; Stoyanov, N.; Lazarova, M.; Aleksiev, B. Aminoderivatives of cycloalkanespirohydantoins: Synthesis and biological activity. Farmaco, 2002, 57(3), 189-194.
[50]
Marinov, M.; Naydenova, E.; Prodanova, R.; Markova, N.; Marinova, P.; Kostova, I.; Valcheva, I.; Draganova, D.; Naydenov, M.; Penchev, P.; Stoyanov, N. Synthesis, characterization, theoretical calculations and antimicrobial studies of substituted 3-amino-cyclohexanespiro-5-hydantoins. Agric. Sci., 2016, 19, 117-122.
[51]
Nagasawa, H.T.; Elberling, J.A.; Shirota, F.N. 2-Aminoadamantane-2-carboxylic acid, a rigid, achiral, tricyclic α-amino acid with transport inhibitory properties. J. Med. Chem., 1973, 16(7), 823-826.
[52]
Marinov, M.; Marinova, P.; Stoyanov, N.; Markova, N.; Enchev, V. Synthesis of 3′,4′-dihydro-2H,2‘H,5H-spiro[imidazolidine-4,1’-naphthalene]-2,5-dione and its derivatives. Acta Chim. Slov., 2014, 61, 420-424.
[53]
Marinov, M.N.; Bakalova, S.M.; Prodanova, R.Y.; Markova, N.V. Conformational and spectral properties of newly synthesized compounds obtained by reaction of alrestatin with 3-amino-cycloalkanespiro-5-hydantoins. Bulg. Chem. Commun., 2017, 49, 146-152.
[54]
Blicharska, B.; Kupka, T. Theoretical DFT and experimental NMR studies on uracil and 5-fluorouracil. J. Mol. Struct., 2002, 613, 153-166.
[55]
d’Antuono, P.; Botek, E.; Champagne, B.; Wieme, J.; Reyniers, M-F.; Marin, G.B.; Adriaensens, P.J.; Gelan, J.M. Density functional theory investigation of the stereochemistry effects on 1H and 13C NMR chemical shifts of poly(vinyl chloride) oligomers. Chem. Phys. Lett., 2005, 411(1-3), 207-213.