Reactivity of δ-substituted α,β-unsaturated cyclic lactones with antileishmanial activity

Molecular Simulation

Volumn 40, Issue 6, 2014, Pages 477-484

  Cardona, Wilson ^a   Guerra, Doris ^a   Restrepo, Albeiro ^a  

^a UNIVERSIDAD DE ANTIOQUIA   (Colombia)

Author keywords

Antileishmanial activity; Molecular descriptors; Reactivity indices

Indexed keywords

ACTIVE COMPOUNDS; FUKUI FUNCTIONS; MICHAEL ACCEPTORS; MOLECULAR DESCRIPTORS; REACTIVITY INDICES; SELECTIVITY INDEX;

CONDENSED MATTER PHYSICS; MOLECULAR STRUCTURE;

ESTERS;

EID: 84892534285     PISSN: 08927022     EISSN: 10290435     Source Type: Journal    
DOI: 10.1080/08927022.2013.822077     Document Type: Article

References (41)

1. Leishmaniasis [Internet]. Geneva: WHO [cited 2012 Dec 29]. Available from: Http://www.who.int/leishmaniasis/en
2. Desjeux P. Leishmaniasis: Current situation and new perspectives. Comp Immunol Microbiol Infect Dis. 2004;27:305-318.
3. Center for Disease Control and Prevention (CDC). The Yellow book, health information for travelers [Internet]. Atlanta, GA: CDC [cited 2012 Oct 2]. Available from: Http://wwwnc.cdc.gov/travel/yellowbook/2010/chapter-5/cutaneous- leishmaniasis.aspx
4. Cardona W, Quiñones W, Echeverri F. Leishmanicidal activity of Passifloricin A and derivatives. Molecules. 2004;9:666-672.
5. Cardona W, Quiñones W, Robledo S, Velez I, Murga J, García-Fortanet J, Carda M, Cardona D, Echeverri F. Antiparasite and antimycobacterial activity of passifloricin analogues. Tetrahedron. 2006;62:4086-4092.
6. Castaño M, Cardona W, Quiñones W, Robledo S, Echeverri F. Leishmanicidal activity of aliphatic and aromatic lactones: Correlation structure-Activity. Molecules. 2009;14:2491-2500.
7. Cardona W, Saez J. Antiprotozoal activity of a;b-Unsaturated d-Lactones: Promising compounds for the development of new therapeutic alternatives. Trop J Pharm Res. 2011;10:671-680.
8. Hoffmann HMR, Rabe J. Synthesis and biological activity of a-Methylene-g-butyrolactones. Angew Chem Int Ed. 1985;24:94-110.
9. Negishi E, Kotora M. Regio- and stereoselective synthesis of g-Alkylidenebutenolides and related compounds. Tetrahedron. 1997;53:6707-6738.
10. Collins I. Saturated and unsaturated lactones. J Chem Soc Perkin Trans. 1999;1:1377-1396.
11. Carter NB, Nadany AE, Sweeney JB. Recent developments in the synthesis of furan-2(5H)-ones. J Chem Soc Perkin Trans. 2002;1:2324-2342.
12. Murakami N, Wang W, Aoki M, Tsutsui Y, Higuchi K, Aoki S, Kobayashi M. Absolute stereostructure of callystatin A, a potent cytotoxic polyketide from the marine sponge, Callyspongia truncata. Tetrahedron Lett. 1997;38:5533-5536.
13. Fang X, Anderson J, Chang C, Mc Laughlin J. Two New Styryl Lactones, 9-Deoxygoniopypyrone and 7-epi-Goniofufurone, from Goniothalamus giganteus. J Nat Prod. 1991;54:1034-1043.
14. Dumonter V, Hung N, Adeline M, Riche C, Chiaroni A, Sévenet T, Guéritte F. Cytotoxic flavonoids and a-Pyrones from cryptocarya obovata. J Nat Prod. 2004;67:858-862.
15. Pereda R, Fragoso M, Cerda C. Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-Tetraacetyloxyheptenyl-5,6-dihydro-A-pyrone from Hyptis spicigera. Tetrahedron. 2001;57:47-53.
16. Hokanson G, French J. Novel antitumor agents CI-920, PD 113 270, and PD 113 271. 3. structure determination. J Org Chem. 1985;50:462-466.
17. De Fatima A, Kohn L, Antonio M, De Carvalho J, Pilli R. Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells. Bioorg Med Chem. 2006;14:622-631.
18. Buck S, Hardouin C, Ichikawa S, Soenen D, Gauss C, Hwang I, Swingle M, Bonness K, Honkanen R, Boger D. Fundamental role of the fostriecin unsaturated lactone and implications for selective protein phosphatase inhibition. J Am Chem Soc. 2003;125:15694-15695.
19. Jaconnet A, Avelona I, Sahpaz S, Terreaux C, Hostettmann K, Stoeckli-Evans H, Rasolondramanitra J. Two 6-substituted 5,6-dihydro-A-pyrones from ravensara anisata. Phytochemistry. 1999;52:265-269.
20. Raoelison G, Terreaux C, Queiroz E, Zsila F, Simonyi M, Antus S, Randriantso A, Hostettmann K. Absolute configuration of two new 6-Alkylated a-Pyrones (-2H-Pyran-2-ones) from ravensara crassifolia. Helv Chim Acta. 2001;84:3470-3476.
21. Kishimoto N, Sugihara S, Mochida K, Fujita T. In vitro antifungal and antiviral activities of g- and d-Lactone analogs utilized as food flavoring. Biocontrol Sci. 2005;10:31-36.
22. Juliawaty L, Kitajima M, Takayama H, Achmad S, Aimi N. A 6-substituted-5,6-dihydro-2-pyrone from cryptocarya strictifolia. Phytochemistry. 2000;54:989-993.
23. Fukushima T, Tanaka M, Gohbara M, Fujimori T. Phytotoxicity of three lactones from Nigrospora sacchari. Phytochemistry. 1998;48:625-630.
24. Schmeda-Hirschmann G, Astudillo L, Bastida J, Codina C, Rojas A, Ferreira M, Inchaustti A, Yaluff G. Cryptofolione derivatives from Cryptocarya alba fruits. J Pharm Pharmacol. 2001;53:563-567.
25. De Fátima A, Marquissolo C, Albuquerque S, Carraro A, Pilli R. Trypanocidal activity of 5,6-dihydropyran-2-ones against free trypomastigotes forms of Trypanosoma cruzi. Eur J Med Chem. 2006;41:1210-1213.
26. Mather B, Viswanathan K, Miller K, Long T. Michael addition reactions in macromolecular design for emerging technologies. Prog Polym Sci. 2006;31:487-531.
27. Gimbert C, Lumbierres M, Marchi C, Moreno-Manas M, Sebastian R, Vallribera A. Michael additions catalyzed by phosphines. an overlooked synthetic method. Tetrahedron. 2005;61:8598-8605.
28. Clayden J, Greeves N, Warren S, Wothers P. Organic chemistry. New York, Chapter 10 Oxford; 2001.
29. Chattaraj P, editor. Chemical reactivity theory: A density functional view. Boca Raton, FL: CRC Press; 2009.
30. Jaramillo C, Guerra D, Moreno L, Restrepo A. Competitive substituent effects on the reactivity of aromatic rings. J Phys Chem A. 2010;114:6033-6038.
31. Geerlings P, De Proft F, Langenaeker W. Conceptual density functional theory. Chem Rev. 2003;103:1793-1874.
32. Mineva T, Sicilia E, Russo N. Density-Functional approach to hardness evaluation and its use in the study of the maximum hardness principle. J Am Chem Soc. 1998;120:9053-9058.
33. Mineva T, Parvanov V, Petrov I, Neshev N, Russo N. Fukui indices from Perturbed Kohn-Sham orbitals and regional softness from mayer atomic valences. J Am Chem Soc. 2001;105:1959-1967.
34. Robledo S, Osorio E, Jaramillo L. In vitro and In vivo cytotoxicities and antileishmanial activities of thymol and hemisynthetic derivatives. Antimicrob Agents Chemother. 2005;49:1652-1655.
35. Taylor V, Muñoz D, Cedeño D, Vélez I, Jones M, Robledo S. Leishmania tarentolae: Utility as an in vitro model for screening of antileishmanial agents. Exp Parasitol. 2010;126:471-475.
36. David J, Guerra D, Restrepo A. Structure and reactivity of the 1Au6Pt clusters. J Phys Chem A. 2010;114:10726-10731.
37. Parr R, Szentpaly L, Liu S. Electrophilicity index. J Am Chem Soc. 1999;121:1922-1924.
38. Gázquez J, Cedillo A, Vela A. Electrodonating and electroaccepting powers. J Phys Chem A. 2007;111:1966-1970.
39. Parr R, Yang W. Density functional approach to the frontierelectron theory of chemical reactivity. J Am Chem Soc. 1984;106:4049-4050.
40. Senet P. Kohn-Sham orbital formulation of the chemical electronic responses, including the hardness. J Chem Phys. 1997;107:2516-2524.
41. Contreras R, Fuentealba P, Galván M, Pérez P. A direct evaluation of regional Fukui functions in molecules. Chem Phys Lett. 1999;304:405-413.