Synthesis of limonene β-amino alcohol derivatives in support of new antileishmanial therapies

Memorias do Instituto Oswaldo Cruz

Volumn 103, Issue 8, 2008, Pages 773-777

  Ferrarini, Stela R ^a   Graebin, Cedric S ^a   Limberger, Jones ^a   Canto, Rômulo F S ^a   Dias, Daiane O ^a   Da Rosa, Ricardo G ^a   De Fátima Madeira, Maria ^b   Eifler Lima, Vera L ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b Funda??o Oswaldo Cruz   (Brazil)

Author keywords

Leishmania braziliensis; Leishmaniasis; Limonene; Neglected diseases; Synthesis; amino alcohol

Indexed keywords

LEISHMANIA BRAZILIENSIS;

EID: 58049164442     PISSN: 00740276     EISSN: 16788060     Source Type: Journal    
DOI: 10.1590/S0074-02762008000800005     Document Type: Article

References (31)

1. Bachi MD, Korshin EE, Ploypradith P, Cumming JN, Xie S, Shapiro TA, Posner GH 1998. Synthesis and in vitro antimalarial activity of sulfone endoperoxides. Bioorg Med Chem Lett 8: 903-908.
2. Belletti N, Ndagijimana M, Sisto C, Guerzoni ME, Lanciotti R, Gardini F 2004. Evaluation of the antimicrobial activity of citrus essences on Saccharomvces cerevisiae. J Agric Food Chem 52: 6932-6938.
3. Chrisman W, Câmara JN, Marcellini K, Singaram B, Goralski CT, Hasha DL, Rudolf, PR, Nicholson LW, Borodychuk KK 2001. A simple and convenient synthesis of β-amino alcohol chiral auxiliaries based on limonene oxide. Tetrahedron Lett 42: 5805-5807.
4. Croft SL, Yeardley V 2002. Chemotherapy of Leishmaniasis. Curr Pharm Design 8: 319-342.
5. Crowell PL, Chang RR, Ren Z, Elson CE, Gould MN 1991. Selective inhibition of isoprenylation of 21-26-kDa proteins by the anticarcinogen d-limonene and its metabolites. J Biol Chem 266: 17679-17685.
6. Deans SG, Ritchie G 1987. Antibacterial properties of plant essential oils. Intl J Food Microbiol 5: 165-180.
7. DNDI - Drugs for Neglected Diseases Initiative 2003. Available from: http://www.dndi.org [cited 2008 May 15].
8. Figueiredo IM, Santos LV, Costa WF, Carvalho JE, Silva CC, Sacoman JL, Kohn KL, Sarragiotto MH 2006. Synthesis and antiproliferative activity of novel limonene derivatives with a substituted Thiourea Moiety. J Braz Chem Soc 17: 954-960.
9. Filipowicz N, Kaminski M, Kurlenda J, Asztemborska M, Ochocka JR 2003. Antibacterial and antifungal activity of juniper berry oil and its selected components. Phytothcr Res 17: 227-231.
10. Graebin CS, Eifler-Lima VL, Rosa RG 2008. One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive animation (hydroaminomethylation). Catal Comm 9: 1066-1070.
11. Jones J Jr, Kover RX, Kover WB, Castro FL 1999. A Novel synthesis of l-Acetyl-4-Isopropenyl-1-Cyclopentene by chemoselective cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: an important intermediate for natural product synthesis. J Braz Chem Soc 10: 112-116.
12. Kim J, Marshall MR, Wei C 1995. Antibacterial activity of some essential oil components against five foodborne pathogens. J Agric Food Chem 43: 2839-2845.
13. Kozhin SA, Zaitsev VV, Ionin BI 1978. Aminolysis products of 1,2-mono-epoxy limonene. Zh Obshch Khim 48: 203-217.
14. Lopes NP, Kato MJ, Andrade EHA, Maia JGS, Yoshida M, Planchart AR, Katzin AM 1999. Antimalarial use of volatile oil from leaves of Virola surinamensis (Rol.) Warb, by Waiãpi Amazon Indians. J Ethnopharmacol 67: 313-319.
15. Machado GMC, Leon LL, Castro SL 2007. Activity of Brazilian and Bulgarian propolis against different species of Leishmania. Mem Inst Oswaldo Cruz 102: 73-77.
16. Mehta G, Shinde HM 2003. Enantiospecific total synthesis of 6-epi-(-)-hamigeran B. Intramolecular Heck reaction in a sterically constrained environment. Tetrahedron Lett 44: 7049-7053.
17. Mosmann T 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunol Methods 65: 55-63.
18. Moura IC, Wunderlich G, Uhrig ML, Couto AS, Peres VJ, Katzin AM, Kimura AE 2001. Limonene arrests parasite development and inhibits isoprenylation of proteins in Plasmodium falciparum. Antimicr Ag Chemother 45: 2553-2558.
19. Murray HW, Berman JD, Davies CR, Saravia NG 2005. Advances in leishmaniasis. Lancet 366: 1561-1577.
20. Newman D, Cragg GM 2007. Natural products as sources of new drugs over the last 25 years. J Nat Prod 70: 461-477.
21. Nostro A, Blanco AR, Cannatelli MA, Enea V, Flamini G, Morelli I, Roccaro AS, Alonzo V 2004. Susceptibility of methicillin-resistant staphylococci to oregano essential oil, carvacrol and thymol. FEMS Microbiology Lett 230: 191 -195.
22. Nwaka S, Hudson A 2006. Innovative lead discovery strategies for tropical diseases. Nature Rev Drug Disc 5: 941-955.
23. Singaram B, Chrisman W, Goralski CT 2002. Chiral amino alcohols and process for preparation of same. World Patent WO0222550. Avaliable from http://www.wipo.int/pctdb/en/wo.jsp?wo=2002022550.
24. Srikrishna A, Dethe DH 2003. Enantiospecific first total synthesis and assignment of absolute configuration of the sesquiterpene (-)-Cucumin H. Org Lett 5: 2295-2298.
25. Steiner D, Sethofer SG, Goralski CT, Singaram B 2002. Asymmetric addition of diethylzinc to aldehydes catalyzed by ß-amino alcohols derived from limonene oxide. Tetrahedron: Asymmetry 13: 1477-1483.
26. Tchoumbougnang F, Zollo PHA, Dagne E, Mekonnen Y 2005. In vivo antimalarial activity of essential oils from Cymbopogon citratus and Ocimum gratissimum on mice infected with Plasmodium berghei. Planta Med 71: 20-23.
27. 3SiH. J Org Chem 68: 7361-7367.
28. Ueda-Nakamura T, Mendonça-Filho RR, Morgado-Díaz JA, Maza PK, Dias Filho BDPAGC, Alviano DS, Rosa MSS, Lopes AHCS, Nakamura CV 2006. Antileishmanial activity of Eugenol-rich essential oil from Ocimum gratissimum. Parasitol Int 55: 99-105.
29. Viegas C Jr, Bolzani VS, Barreiro EJ 2006. Os produtos naturais e a química medicinal moderna. Quim Nova 29: 326-337.
30. Wender PA, Bi FC, Brodney MA, Gosselin F 2001. Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition. Org Lett 3: 2105-2108.
31. WHO-World Health Organization 2008. Leishmaniasis: Background Information. Available from: http://www.who.int/leishmaniasis/ en [updated 2008 Mar 13; cited 2008 May 15].