A Multidisciplinary Approach to the Study of Adamantyl Aminoguanidines – A New Class of Potentially Bioactive Compounds

Abstract

Although adamantyl aminoguanidines have great potential as pharmacophores, their preparation and characterization has only recently been described. A detailed study of this class of compounds is presented here, with special emphasis on their physico-chemical properties as well as the evaluation of their biological application.

Key words

adamantane - aminoguanidine - liposomes - enzyme inhibition - anion receptors

• References

• 1 Fort RC. Jr. Adamantane – The Chemistry of Diamond Molecules . Marcel Dekker; New York: 1976
• 2a Lamoureux G, Artavia G. Curr. Med. Chem. 2010; 17: 2967
• 2b Liu J, Obando D, Liao V, Lifa T, Codd R. Eur. J. Med. Chem. 2011; 46: 1949
• 2c Wanka L, Iqbal K, Schreiner PR. Chem. Rev. 2013; 113: 3516
• 3a Nishimura T, Toku H, Fukuyasu H, Kawakami M, Kazuno Y, Sekizawa Y. Kitasato Arch. Exp. Med. 1979; 52: 15
• 3b Cooper MJ, Hull R, Wardleworth M. J. Chem. Soc., Perkin Trans. 1 1975; 1433
• 3c Györgydeák Z, Holzer W. Heterocycles 1998; 48: 1395
• 3d Papanastasiou I, Tsotinis A, Kolocouris N, Prathalingam SR, Kelly JM. J. Med. Chem. 2008; 51: 1496
• 3e Papanastasiou I, Tsotinis A, Zoidis G, Kolocouris N, Prathalingam SR, Kelly JM. ChemMedChem 2009; 4: 1059
• 4 Šekutor M, Glasovac Z, Mlinarić-Majerski K. J. Phys. Chem. A 2013; 117: 2242
• 5 Šekutor M, Štimac A, Mlinarić-Majerski K, Frkanec R. Org. Biomol. Chem. 2014; 12: 6005
• 6 Šekutor M. Doctoral Thesis (in Croatian). University of Zagreb; Croatia: 2013
• 7 Šekutor M, Mlinarić-Majerski K. Tetrahedron Lett. 2014; 55: 6665
• 8 Šekutor M, Mlinarić-Majerski K, Hrenar T, Tomić S, Primožič I. Bioorg. Chem. 2012; 41-42: 28
• 9a Geluk HW, Schlatmann JL. M. A. Recl. Trav. Chim. Pays-Bas 1971; 90: 516
• 9b Faulkner D, McKervey MA. J. Chem. Soc. C 1971; 3906
• 9c Gilbert EE. Synth. Commun. 1985; 15: 53
• 9d Marchand AP, Allen RW. J. Org. Chem. 1974; 39: 1596
• 9e Lavrova LN, Klimova NV, Shmar’yan MI, Uljanova OV, Vihlajev YI, Skoldinov AP. Zh. Org. Khim. 1974; 10: 761
• 9f Davis MC, Nissan DA. Synth. Commun. 2006; 36: 2113
• 9g Jaroskova L, Van der Veken L, de Belser P, Diels G, de Groot A, Linders JT. M. Tetrahedron Lett. 2006; 47: 8063
• 10 Glaser R, Steinberg A, Šekutor M, Rominger F, Trapp O, Mlinarić-Majerski K. Eur. J. Org. Chem. 2011; 3500
• 11a Mlinarić-Majerski K, Vinković M, Škare D, Marchand AP. ARKIVOK 2002; (iv): 30
• 11b Paddon-Row MN. Tetrahedron 1994; 50: 10813
• 12a Springs B, Haake P. Bioorg. Chem. 1977; 6: 181
• 12b Sapse AM, Russell CS. Int. J. Quantum Chem. 1984; 26: 91
• 12c Sapse AM, Russell CS. J. Mol. Struct. (Theochem.) 1986; 137: 43
• 12d Luo R, David L, Hung H, Devaney J, Gilson MK. J. Phys. Chem. B 1999; 103: 727
• 13a Kato Y, Conn MM, Rebek JJr. J. Am. Chem. Soc. 1994; 116: 3279
• 13b Fitzmaurice RJ, Kyne GM, Douheret D, Kilburn JD. J. Chem. Soc., Perkin Trans. 1 2002; 841
• 13c Schug KA, Lindner W. Chem. Rev. 2005; 105: 67
• 13d Schmuck C. Coord. Chem. Rev. 2006; 250: 3053
• 13e Blondeau P, Segura M, Perez-Fernandez R, de Mendoza J. Chem. Soc. Rev. 2007; 36: 198
• 14 Darvesh S, McDonald RS, Darvesh KV, Mataija D, Conrad S, Gomez G, Walsh R, Martin E. Bioorg. Med. Chem. 2007; 15: 6367
• 15a Giacobini E. Drugs Aging 2001; 18: 891
• 15b Jann MW. Pharmacotherapy 2000; 20: 1
• 16 Chan HM, Boxer SG. Curr. Opin. Chem. Biol. 2007; 11: 581
• 17a Lättig-Tunnemann G, Prinz M, Hofmann D, Behlke J, Palm-Apergi C, Morano I, Herce HD, Cardoso MC. Nat. Commun. 2011; 2: 453
• 17b Rothbard JB, Jessop TC, Lewis RS, Murray BA, Wender PA. J. Am. Chem. Soc. 2004; 126: 9506
• 17c Wheaten SA, Ablan FD. O, Spaller BL, Trieu JM, Almeida PF. J. Am. Chem. Soc. 2013; 135: 16517