Synthesis and comparison of antimalarial activity of febrifugine derivatives including halofuginone

Medicinal Chemistry

Volumn 5, Issue 3, 2009, Pages 293-300

  Samant, Bhupesh S ^a,c   Sukhthankar, Mugdha G ^b  

^a UNIVERSITY OF MUMBAI   (India)

^b UNIVERSITY OF TENNESSEE   (United States)

^c UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

3 Hydroxy picoline; Antimalarial; Antiprotozoal; Coccidiostat; Halofuginone

Indexed keywords

1 [2' [3' (ACETYLOXY) 1' (OXO)PIPERIDINO]] 3 BROMO 2 PROPANONE; 1 [2' [3' (ACETYLOXY) 1' (OXO)PYRIDINO]] 3 BROMO 2 PROPANONE; 1 [2' [3' (ACETYLOXY) 1' (OXO)PYRIDINO]]ACETYL CHLORIDE; 1 [2' [3' (HYDROXY) 1' (OXO)PYRIDINO]]ACETIC ACID; 1 [2' [3' (HYDROXY) 1' (OXO)PYRIDINO]]ETHYLACETATE; 3 [2 OXO 3 (3 METHOXY 2 PIPERIDYL)PROPYL] 6 BROMO 7 CHLORO METHYLENEDIOXY 4 QUINAZOLONE; 3 ACETYLOXY 2 (3 BROMO 2 PROPANONE)PIPERIDINE 1 OXIDE; 3 ACETYLOXY 2 (3 BROMO 2 PROPANONE)PYRIDINE 1 OXIDE; 3 ACETYLOXY 2 ACETYL CHLORIDE PYRIDINE 1 OXIDE; 3 HYDROXY 2 (1 METHYLACETO)PYRIDINE 1 OXIDE; 3 HYDROXY 2 ACETIC ACID PYRIDINE 1 OXIDE; 3 HYDROXY 2 METHYL PYRIDINE 1 OXIDE; 3,4 METHYLENEDIOXY 5 NITROBENZALDEHYDE; 3,4 METHYLENEDIOXY 6 NITROBENZALDEHYDE; 3,4 METHYLENEDIOXYBENZALDEHYDE; 6 BROMO 5 CHLORO 4 QUINAZOLONE; ANTIMALARIAL AGENT; BENZOIC ACID DERIVATIVE; CHLOROQUINE; FEBRIFUGINE; HALOFUGINONE; METHYL 2 AMINO 4,5 METHYLENEDIOXY BENZOIC ACID; PICOLINE DERIVATIVE; SURFACTANT; UNCLASSIFIED DRUG; PIPERIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; QUINAZOLINONE DERIVATIVE;

ANIMAL CELL; ANTIMALARIAL ACTIVITY; ANTIMALARIAL DRUG RESISTANCE; ANTIMALARIAL DRUG SUSCEPTIBILITY; ARTICLE; CELL LINE; CHEMICAL REACTION; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; ISOMER; MACROPHAGE; MAMMAL CELL; NERVE CELL; NITRATION; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; ANIMAL; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; SYNTHESIS;

ANIMALS; ANTIMALARIALS; BENZOIC ACIDS; CELL LINE; PIPERIDINES; PLASMODIUM FALCIPARUM; QUINAZOLINES; QUINAZOLINONES;

EID: 67651174574     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340609788185846     Document Type: Article

References (25)

1. (a) Koepfli, J.B.; Mead, J.F. Jr.; Brockman, J.A. An alkaloid with high antimalarial activity from dichroa-febrifuga. J. Am. Chem. Soc., 1947, 69, 1837
2. (b) Zhu, S.; Meng, L.; Zhang, Q.; Wei, L. Synthesis and evaluation of febrifugine analogues as potential antimalarial agents. Bioorg. Med. Chem. Lett., 2006, 16, 1854-8.
3. a) Jang, C.S.; Fu, F.Y.; Wang, C.Y.; Huang, K.C.; Lu, G.; Chou, T.C. Chang Shan, a Chinese antimalarial herb. Science, 1946, 103, 59
4. b) Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H. Catalytic asymmetric synthesis of febrifugine and isofebrifugine. Tetrahedron Lett., 1999, 40, 2175-8
5. c) Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H., Kim, H.S.; Wataya, Y. Catalytic asymmetric synthesis of antimalarial alkaloids febrifugine and isofebrifugine and their biological activity J. Org. Chem., 1999, 64, 6833-41.
6. Mital, A. Recent advances in antimalarial compounds and their patents. Curr. Med. Chem., 2007, 14, 759-73.
7. Murata, K.; Takano, F.; Fushiya, S.; Oshima, Y. Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga. J. Nat. Prod., 1998, 61, 729-33.
8. Pines, M.; Vlodavsky, I.; Nagler, A. Halofuginone: From veterinary use to human therapy. Drug Dev. Res., 2000, 50, 371-8.
9. Abramovitch, R.; Itzik, A.; Harel, H.; Nagler, A.; Vlodavsky, I.; Siegal, T. Halofuginone inhibits angiogenesis and growth in implanted metastatic rat brain tumor model - an MRI study. Neoplasia, 2004, 6, 480-9.
10. Gnainsky, Y.; Kushnirsky, Z.; Bilu, G.; Hagai, Y.; Genina, O.; Volpin, H.; Bruck, R.; Spira, G.; Nagler, A.; Kawada, N.; Yoshizato, K.; Reinhardt, D. P.; Libermann, T. A.; Pines, M. Gene expression during chemically induced liver fibrosis: effect of halofuginone on TGF-beta signaling. Cell Tissue Res., 2007, 328, 153-66.
11. McDougald, L.R.; Seibert, B.P. Residual activity of anticoccidial drugs in chickens after withdrawal of medicated feeds. Vet. Parasitol., 1998, 74, 91-9.
12. Heckeroth, A.R.; Wackwitz, C.; Gawlowska, S.; Mackenstedt, U.; Kliemt, D.; Daugschies, A. Development and validation of a cell culture based assay for in vitro assessment of anticryptosporidial compounds. Parasitol. Res., 2007, 101, 161-7
13. Pouliquen, H. Only halofuginone is authorised agained Cryptosporidiosis. Point Vet., 2007, 38, 77.
14. Ernst, R.A.; Vohra, P.; Kratzer, F.H.; Jr. Kuhl, H. J. Effect of halofuginone (Stenorol) on chukar partridge (Alectoris chukar). Poult. Sci., 1996, 75, 1493-5.
15. Takeuchi, Y.; Koike, M.; Azuma, K.; Nishioka, H.; Abe, H.; Kim, H.S.; Wataya, Y.; Harayama, T. Synthesis and antimalarial activity of febrifugine derivatives. Chem. Pharm. Bull., 2001, 49, 721-5
16. Ashoorzadeh, A.; Caprio, V. A convergent enantioselective synthesis of the anti-malarial agent (+)-febrifugine. Synlett, 2005, 2, 346-8 reference number 4 there in.
17. Baker, B.R.; McEvoy, F.J.; Schaub, R.E.; Joseph, J.P.; Williams, J.H. An antimalarial alkaloid from hydrangea.21. Synthesis and structure of febrifugine and isofebrifugine, J. Org. Chem., 1953, 18, 178-83.
18. Chien, P.L.; Cheng, C.C. Structural modification of febrifugine-some methylenedioxy analogs. J. Med. Chem., 1970, 13, 867-70.
19. Koepfli, J.B.; Mead, J.F.; Jr. Brockman, J.A. Alkaloids of dichroa-febrifuga.1. Isolation and degradative studies. J. Am. Chem. Soc., 1949, 71, 1048-54
20. Uesato, S., Kuroda, Y.; Kato, M.; Fujiwara, Y.; Hase, Y.; Fujita, T. Conformational analysis of febrifugines and halofuginones in organic solvents. Chem. Pharm. Bull., 1998, 46, 1-5
21. Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T. Synthesis of D/ L-febrifugine and D/L-isofebrifugine. Synthesis, 1999, 10, 1814-8.
22. Chhatre, A.S.; Joshi, R.A.; Kulkarni, B.D. Microemulsions as media for organic-synthesis-selective nitration of phenol to orthonitrophenol using dilute nitric acid. J. Colloid interface Sci., 1993, 158, 183-7
23. Samant, B.S.; Saraf, Y.P.; Bhagwat, S.S. Chlorination of aromatic compounds in micellar media: Regioselectivity. J. Colloid Interface Sci., 2006, 302, 207-13.
24. Trager, W.; Jensen, J.B. Human malaria parasites in continuous culture. Science, 1976, 193, 673-5.
25. Jiang, S.P; Prigge, S.T.; Wei, L.; Gao, Y-E.; Hudson, T.H.; Gerena, L.; Dame, J.B.; Kyle, D.E. New class of small nonpeptidyl compounds blocks Plasmodium falciparum development in vitro by inhibiting plasmepsins. Antimicrob. Agents Chemother., 2001, 193, 2577-84.