Synthesis and evaluation of β-carbolinium cations as new antimalarial agents based on π-delocalized lipophilic cation (DLC) hypothesis

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 6, 2005, Pages 653-661

  Takasu, Kiyosei ^a   Shimogama, Tsubasa ^a   Saiin, Chalerm ^a   Kim, Hye Sook ^b   Wataya, Yusuke ^b   Brun, Reto ^c   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

Author keywords

Carbolinium salt; delocalized lipophilic cationic (DLC) hypothesis; Antimalarial agent; Structure activity relationship; Total synthesis; Tropical disease

Indexed keywords

ANTILEISHMANIAL AGENT; ANTIMALARIAL AGENT; ANTITRYPANOSOMAL AGENT; BETA CARBOLINE DERIVATIVE; CATION;

ANIMAL CELL; ANIMAL TISSUE; ANTIMALARIAL ACTIVITY; ARTICLE; CATION TRANSPORT; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HYPOTHESIS; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PI DELOCALIZED LIPOPHILIC CATION HYPOTHESIS;

ANIMALS; ANTIMALARIALS; CARBOLINES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; MALARIA; MALE; MICE; MICE, INBRED ICR; PLASMODIUM BERGHEI;

EID: 21144445234     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.53.653     Document Type: Article

References (48)

1. The World Health Report 2002: 〈http://www.who.int/whr/2002/en/ 〉, World Health Organization (WHO) Web.
2. Drugs for Neglected Diseases Institute: 〈http://www.dndi.org/〉, DNDi Web.
3. Rosenthal P. J., Miller L. H., "Antimalarial Chemotherapy," ed. by Rosenthal P. J., Humana Press, New Jersy, 2001, pp. 3-15.
4. Go M.-L., Med. Res. Rev., 23, 456-487 (2003), and references cited therein.
5. Takasu K., Inoue H., Kim H.-S., Suzuki M., Shishido T., Wataya Y., Ihara M., J. Med. Chem., 45, 995-998 (2002).
6. Takasu K., Terauchi H., Inoue H., Kim H.-S., Wataya Y., Ihara M., J. Combi. Chem., 5, 211-214 (2003).
7. Takasu K., Terauchi H., Inoue H., Takahashi M., Sekita S., Ihara M., Heterocycles, 64, 215-221 (2004).
8. Chen L. B., Ann. Rev. Cell Biol., 4, 155-181 (1988).
9. Kawakami M., Koya K., Ukai T., Tatsuta N., Ikegawa A., Ogawa K., Shishido T., Chen L. B., J. Med. Chem., 40, 3151-3160 (1997).
10. Modica-Napolitano J. S., Aprille J. R., Adv. Drug Deliv. Rev., 49, 63-70 (2001).
11. Weissig V., Torchilin V. P., Adv. Drug Deliv. Rev., 49, 127-149 (2001).
12. Srivastava I. K., Rottenberg H., Vaidya A. B., J. Biol. Chem., 272, 3961-3966 (1997).
13. Ang K. K. H., Holmes M. J., Higa T., Hamann M. T., Kara U. A. K., Antimicrob. Agents Chemother., 44, 1645-1649 (2000).
14. Chan K. L., O'Neill M. J., Phillipson J. D., Warhurst D. C., Planta Med., 1986, 105-107 (1986).
15. Wright C. W., Bray D. H., O'Neill M. J., Warhurst D. C., Phillipson J. D., Quetin-Leclercq J., Angenot L., Planta Med., 57, 337-343 (1991).
16. MVC was first isolated and its structure was determined in 1970, see: Johns S. R., Lamberton J. A., Sioumis A. A., Aust. J. Chem., 23, 629-630 (1970).
17. Pavanand K., Yongvanitchit K., Webster H. K., Dechatiwongse T, Nutakul W, Jewvachdamrongkul Y., Bansiddhi J., Phytother. Res., 2, 33-36 (1988).
18. A part of this work was published as preliminary communication: Takasu K., Shimogama T, Saiin C., Kim H.-S., Wataya Y., Ihara M., Bioorg. Med. Chem. Lett., 14, 1689-1692 (2004).
19. Sanchez E., Comin J., An. Asoc. Quim. Argent., 57, 57-59 (1969).
20. Cain M., Mantei R., Cook J. M., J. Org. Chem., 47, 4933-4936 (1982).
21. Hagen T. J., Narayanan K., Names J., Cook J. M., J. Org. Chem., 54, 2170-2178 (1989).
22. Suzuki H., Iwata (nee Miyagi) C., Sakurai K., Tokumoto K., Takahashi H., Hanada M., Yokoyama Y., Murakami Y., Tetrahedron, 53, 1593-1606 (1997).
23. Yang J.-S., Luo S.-R., Shen X.-L., Li Y.-X., Yao Hsueh Hsueh Pao, 14, 167-177 (1979).
24. Yang J.-S., Gong D., Acta Chim. Sinica, 42, 679-683 (1984).
25. Blackman A. J., Matthews D. J., Narkowicz C. K., J. Nat. Prod., 50, 494-496 (1987).
26. Jordaan A., Du Plessis L. M., Joynt V. P., J. South African Chem. Inst., 21, 22-25 (1968).
27. Haynes H. F., Nelson E. R., Price J. R., Aust. J. Sci. Res., A5, 387-400 (1952).
28. Quite recently, one-pot synthesis of canthin-6-one from 1-formyl-β-carboline was reported: Suzuki H., Adachi M., Ebihara Y., Gyoutoku H., Furuya H., Murakami Y., Okuno H., Synthesis, 2005, 28-32 (2005).
29. Ho B.-T., McIsaac W. M., Tansey L. W., Walker K. E., Can. J. Chem., 45, 2963-2967 (1967).
30. Compound 6b; Johns S. R., Lamberton J. A., Sioumis A. A., Aust. J. Chem., 23, 629-630 (1970).
31. Matia M. P., Ezquerra J., Garcia-Navio J. L., Vaquero J. J., Alvarez-Builla J., Tetrahedron Lett., 32, 7575-7578 (1991).
32. Yoshino H., Koike K., Nikaido T., Heterocycles, 51, 281-293 (1999).
33. Shiroyan F. R., Terzyan A. G., Tatevaosyan G. T., Izv. Akad. Nauk ArmSSR, Khim. Nauki, 18, 606-614 (1965).
34. Another examples of compounds that have enhanced antiplasmodial activity compared to its non-quarternarized presursor. See references 35-37: Wright C. W., Phillipson J. D., Awe S. O., Kirby G. C., Warhurst D. C., Quetin-Leclercq J., Angenot L., Phytother. Res., 10, 361-363 (1996).
35. Wright C. W., Addae-Kyereme J., Breen A. G., Brown J. E., Cox M. F., Croft, S. L., Gökçek Y., Kendrick H., Phillios R. M., Pollet P. L., J. Med. Chem., 44, 3187-3194 (2001).
36. Iwasa K., Moriyasu M., Tachibana Y., Kim H.-S., Wataya Y., Wiegrebe W, Bastow F., Cosentino L. M., Kozuka M., Lee K.-H., Bioorg. Med. Chem., 9, 2871-2884 (2001).
37. Vennerstrom J. L., Makler M. T., Angerhofer C. K., Williams J. A., Antimicrob. Agents Chemther., 39, 2671-2677 (1995).
38. Matsubara K., Senda T., Uezono T., Fukushima S., Ohta S., Igarashi K., Naoi M., Yamashita Y., Ohtaki K., Hayase N., Akutsu S., Kimura K., Eur. J. Pharm., 348, 77-84 (1998).
39. Peters W., Portus J. H., Robinson B. L., Ann. Trop. Med. Parasitol., 69, 155-171 (1975).
40. Peters W., Richards W. H. G., "Current Antimalarials and New Drug Developments," Splinger-Verlag, Berlin, 1984, pp. 229-230.
41. Trager W., Jensen J. B., Science, 193, 673-675 (1976).
42. Yoshioka A., Tanaka S., Hiraoka O., Koyama Y., Hirota Y., Asyusawa D., Seno T., Garrett C., Wataya Y., J. Biol. Chem., 262, 8235-8241 (1987).
43. Kim H.-S., Shibata Y., Wataya Y., Tsuchiya K., Masuyama A., Nojima M., J. Med. Chem., 42, 2604-2609 (1999).
44. Takaya Y., Tasaka H., Chiba T., Uwai K., Tanitsu M., Kim H.-S., Wataya Y., Miura M., Takeshita M., Oshima Y., J. Med. Chem., 42, 3163-3166 (1999).
45. Matile H., Pink J. R. L., "Immunological Methods," ed. by Lefkovits I., Pernis B., Academic Press, San Diego, 1990, pp. 221-234.
46. Ismail M. A., Brun R., Easterbrook J. D., Tanious F. A., Wilson W. R., Boykin D. W., J. Med. Chem., 46, 4761-4769 (2003).
47. Mbwambo Z. H., Apers S., Moshi M. J., Kapingu M. C., Van Miert S., Brun R., Cos P., Pieters L., Vlietinck A., Planta Med., 70, 706-710 (2004).
48. Van Miert S., Van Dyck S., Schmidt T. J., Brun R., Vietinck A., Lemière G., Pieters L., Bioorg. Med. Chem., 13, 661-669 (2005).