Synthesis and antifungal activities of miltefosine analogs

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 17, 2013, Pages 4828-4831

  Ravu, Ranga Rao ^a   Chen, Ying Lien ^b   Jacob, Melissa R ^a   Pan, Xuewen ^c   Agarwal, Ameeta K ^a   Khan, Shabana I ^a,d   Heitman, Joseph ^b   Clark, Alice M ^a,d   Li, Xing Cong ^a,d  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

^c BAYLOR COLLEGE OF MEDICINE   (United States)

^d UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Alkylphosphocholine; Antifungal; Candidiasis; Cryptococcosis; Miltefosine

Indexed keywords

ALKYL GROUP; AMPHOTERICIN B; ANTIFUNGAL AGENT; CHOLINE; DOXORUBICIN; MILTEFOSINE; N (4 METHOXYBENZYLL) N,N DIMETHYL 2 [[(HEXADECYLOXY)HYDROXYPHOSPHINYL]OXY]ETHANAMINIUM INNER SALT; N BENZYL N,N DIMETHYL 2 [[(HEXADECYLOXY)HYDROXYPHOSPHINYL]OXY]ETHANAMINIUM INNER SALT; N,N DIMETHYL N (4 NITROBENZYL) 2 [[(HEXADECYLOXY)HYDROXYPHOSPHINYL]OXY]ETHANAMINIUM INNER SALT; PHOSPHORYLCHOLINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDA GLABRATA; CANDIDA KRUSEI; CANDIDIASIS; CHEMICAL MODIFICATION; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG CYTOTOXICITY; DRUG DOSE REDUCTION; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MAMMAL CELL; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; SYSTEMIC MYCOSIS;

ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDA GLABRATA; FILOBASIDIELLA NEOFORMANS; ISSATCHENKIA ORIENTALIS; MAMMALIA;

ALKYLPHOSPHOCHOLINE; ANTIFUNGAL; CANDIDIASIS; CRYPTOCOCCOSIS; MILTEFOSINE;

ANIMALS; ANTIFUNGAL AGENTS; ASPERGILLOSIS; ASPERGILLUS FUMIGATUS; CANDIDA; CANDIDIASIS; CELL LINE; CRYPTOCOCCOSIS; CRYPTOCOCCUS NEOFORMANS; FUNGI; HUMANS; MICE; MYCOSES; PHOSPHORYLCHOLINE;

EID: 84881369581     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.06.096     Document Type: Article

References (30)

1. S.R. Vink, W.J. Van Blitterswijk, J.H. Schellns, and M. Verheij Cancer Treat. Rev. 33 2007 191
2. H. Eibl, and C. Unger Cancer Treat. Rev. 17 1990 233
3. W.J. Houlihan, M. Lohmeyer, P. Workman, and S.H. Cheon Med. Res. Rev. 15 1995 157
4. K. Seifert, A. Lemke, S.L. Croft, and O. Kayser Antimicrob. Agents Chemother. 51 2007 4525
5. T.P. Dorlo, P.P. van Thiel, A.D. Huitema, R.J. Keizer, H.J. de Vries, J.H. Beijnen, and P.J. de Vries Antimicrob. Agents Chemother. 52 2008 2855
6. D. Llull, L. Rivas, and E. Garcia Antimicrob. Agents Chemother. 2007 1844 51
7. S.L. Croft, K. Seifert, and M. Duchene Mol. Biochem. Parasitol. 126 2003 165
8. P. Chugh, B. Bradel-Tretheway, C.M.R. Monteiro-Filho, V. Planelles, S.B. Maggirwar, S. Dewhurst, and B. Kim Retrovirology 5 2008 11
9. Q. Lu, R.P. Ubillas, Y. Zhou, L.G. Dubenko, J.M. Dener, J. Litvak, P.W. Phuan, M. Flores, Z. Ye, R.E. Gerber, T. Truong, and D.E. Bierer J. Nat. Prod. 62 1999 824
10. F. Widmer, L.C. Wright, D. Obando, R. Handke, R. Ganendren, D.H. Ellis, and T.C. Sorrell Antimicrob. Agents Chemother. 50 2006 414
11. Z. Tong, F. Widmer, T.C. Sorrell, Z. Guse, K.A. Jolliffe, C. Halliday, O.C. Lee, F. Kong, L.C. Wright, and S.C.A. Chen Antimicrob. Agents Chemother. 51 2007 2219
12. T.V.M. Vila, K. Ishida, W. de Souza, K. Prousis, T. Calogeropoulou, and S. Rozental J. Antimicrob. Chemother. 68 2013 113
13. X. Zuo, J.T. Djordjevic, J. Bijosono Oei, S.D. Schibeci, K.A. Jolliffe, and T.C. Sorrell Mol. Pharmacol. 80 2011 476
14. D. Berkovic, S. Sievers, D. Haase, E.A. Fleer, and C. Binder J. Exp. Ther. Oncol. 2 2002 85
15. M.P. Carrasco, J.M. Jimenez-Lopez, J.L. Segovia, and C. Marco FEBS J. 275 2008 1675
16. G.A. Ruiter, S.F. Zerp, H. Bartelink, W.J. van Blitterswijk, and M. Verheij Anticancer Drugs 14 2003 167
17. A.H. van der Luit, M. Budde, P. Ruurs, M. Verheij, and W.J. van Blitterswijk J. Biol. Chem. 277 2002 39541
18. N.P. Wiederhold, L.K. Najvar, R. Bocanegra, W.R. Kirkpatrick, T.C. Sorrell, and T.F. Patterson Antimicrob. Agents Chemother. 57 2013 745
19. A. Breiser, D.-J. Kim, E.A. Fleer, W. Damenz, A. Drube, M. Berger, G.A. Nagel, H. Eibl, and C. Unger Lipids 22 1987 925
20. D. Arndt, R. Zeisig, I. Fichtner, A.D. Teppke, and A. Fahr Breast Cancer Res. Treat. 58 1999 71
21. D. Obando, F. Widmer, L.C. Wright, T.C. Sorrell, and K.A. Jolliffe Bioorg. Med. Chem. 15 2007 5158
22. M. Lukáč, M. Mrva, E. Fischer-Fodor, I. Lacko, M. Bukovský, N. Miklášová, F. Ondriska, and F. Devínsky Bioorg. Med. Chem. Lett. 19 2009 6346
23. M. Lukáč, J. Mojžiš, G. Mojžiš ová, M. Mrva, F. Ondriska, J. Valentová, I. Lacko, M. Bukovský, F. Devínsky, and J. Karlovská Eur. J. Med. Chem. 44 2009 4970
24. Perrissoud, D.; Pietras, M.; Engel, J. PCT Int. Appl. 2007, WO 2007071658 A2 20070628.
25. M.S. Karabit, O.T. Juneskans, and P. Lundgren Int. J. Pharm. 46 1988 141
26. A. Mosca, F. Russo, and G. Miragliotta J. Antimicrob. Chemother. 57 2006 566
27. Advanced Chemistry Development, Inc. ACD/Structure Designer Suite 12.0. Toronto, ON, Canada. http://www.acdlabs.com/products/pc-admet/physchem/sds/.
28. A. Salmon, and P. Jutzi J. Organomet. Chem. 637-639 2001 595
29. X.-C. Li, M.R. Jacob, S.I. Khan, M.K. Ashfaq, K.S. Babu, A.K. Agarwal, H.N. ElSohly, S.P. Manly, and A.M. Clark Antimicrob. Agents Chemother. 52 2008 2442
30. C.-R. Yang, Y. Zhang, M.R. Jacob, S.I. Khan, Y.-J. Zhang, and X.-C. Li Antimicrob. Agents Chemother. 50 2006 1710