Synthesis and in vitro antimalarial activity of sulfone endoperoxides

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 8, 1998, Pages 903-908

  Bachi, Mario D ^a   Korshin, Edward E ^a   Ploypradith, Poonsakdi ^b   Cumming, Jared N ^b   Xie, Suji ^c   Shapiro, Theresa A ^c   Posner, Gary H ^b  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b JOHNS HOPKINS UNIVERSITY   (United States)

^c JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4,8 DIMETHYL 4 PHENYLSULFONYLMETHYL 2,3 DIOXABICYCLO[3.3.1]NONANE; ARTEFLENE; ARTEMISIN; DNA; ENDOPEROXIDE; LIMONENE; UNCLASSIFIED DRUG; YINGZHAOSU A;

ACYLATION; ALKYLATION; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; TRADITIONAL MEDICINE;

ANIMALS; ANTIMALARIALS; CHLOROQUINE; DRUGS, CHINESE HERBAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PEROXIDES; PLASMODIUM FALCIPARUM; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES;

EID: 0032554709     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00141-3     Document Type: Article

References (33)

1. 1. Butler, D.; Maurice, J.; Clare, O. Nature 1997, 386, 535.
2. 2. Jung, M. Curr. Med. Chem. 1994, 1, 46.
3. 3. Butler, A. R.; Wu, Y.-L. Chem. Soc. Rev. 1992, 85.
4. 4. Meshnick, S. R.; Taylor, T. E.; Kamchonowngpaisan, S. Microbiological Reviews 1996, 60, 301.
5. 5. Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmacol. 1997, 37, 253.
6. 6. Jefford, C. W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gerard, D.; Burger, U.; Kamalaprija, D.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C. J.; Fleck, S. L.; Robinson, B. L, Peters, W. Helv. Chim. Acta 1995, 78, 647.
7. 7. Posner, G. H.; Park, S. B.; González, L.; Wang, D.; Gumming, J. N.; Klinedinst, D.; Shapiro, T. A.; Bachi, M. D. J. Am. Chem. Soc. 1996, 118, 3537.
8. 8. Avery, M. A.; Mehrotra, S.; Johnson, T. L.; Bonk, J. D.; Vroman, J. A.; Miller, R. J. Med. Chem. 1996, 39, 4149.
9. 9. Avery, M. A.; Gao, F.; Chong, W. K. M.; Hendrickson, T. F.; Inman, W. D.; Crews, P. Tetrahedron 1994, 50, 957.
10. 10. Liang, X. T.; Yu, D. Q.; Wu, W. L.; Deng, H. C. Acta Chim. Sin. 1979, 37, 215.
11. 11. Xu, X. X.; Zhu, J.; Haung, D.; Zhou, W. Tetrahedron Lett. 1991, 32, 5785.
12. 12. Hofheinz, W.; Burgin, H.; Gocke, E.; Jaquet, C.; Masciadri, R.; Schmid, G.; Stohler, H.; Urwyler, H. Trop. Med. Parasitol. 1994, 45, 261.
13. 13. Jaquet, C.; Stohler, H. R.; Chollet, J.; Peters, W. Trop. Med. Parasitol. 1994, 45, 266.
14. 14. Rosenthal, P. J.; Olson, J. E.; Lee, G. K.; Palmer, J. T.; Klaus, J. L.; Rasnick, D. Antimicrob. Agents Chemother. 1996, 40, 1600.
15. 15. For antimalarial activity of sulfone trioxanes see reference 16.
16. 16. Posner, G. H.; O'Dowd, H.; Caferro, T.; Cumming, J. N.; Ploypradith, P.; Xie, S.; Shapiro, T. A. Tetrahedron Lett., in press.
17. 17. Reaction mechanism and experimental protocol for the reactions described in Scheme 1 are detailed in: Bachi, M. D.; Korshin, E. E. Synlett. 1998, 122.
18. 18. A similar effect is described in reference 16.
19. 19. Avery, M. A.; Gao, F.; Chong, W. K. M.; Mehrotra, S.; Milhous, W. K. J. Med. Chem. 1993, 36, 4264.
20. 20. Posner, G. H.; Oh, C. H.; Gerena, L.; Milhous, W. K. J. Med. Chem. 1992, 35, 2459.
21. 21. Posner, G. H.; McGarvey, D.; Oh, C. H.; Kumar, N.; Meshnick, S. R.; Asawamahasadka, W. J. Med. Chem. 1995, 35, 607.
22. 22. Posner, G. H.; Oh, C. H.; Gerena, L.; Milhous, W. K. Heteroatom. Chem. 1995, 6, 105.
23. 13C HMQC), and by elemental microanalysis or CI HRMS.
24. 6S (M + 1) 447.18414.
25. 25. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
26. 26. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Antimicrob. Agents Chemother. 1979, 16, 710.
27. 27. Milhous, W. K.; Weatherly, N. F.; Bowdre, J. H.; Desjardins, R. Antimicrob. Agents Chemother. 1985, 27, 525.
28. 28. Posner, G. H.; Gonzales, L.; Cumming, J. N.; Klinedinst, D.; Shapiro, T. A. Tetrahedron 1997, 53, 37.
29. 1H NMR between epimers at C(4) a and b see reference 17.
30. 30. Posner, G. H.; Ployapradith, P.; Hapangama, W.; Wang, D.; Cumming, J. N.; Dolah, P.; Kensler, T. W.; Klinedinst, D.; Shapiro, T. A.; Zheng, Q. Y.; Murray, C. K.; Pilkington, L. G.; Jayasinghe, L. R.; Bray, J. F.; Daughenbauth, R. Bioorg. Med. Chem. 1997, 5, 1257.
31. 31. Avery, M. A.; Bonk, J. D.; Chong, W. K. M.; Mehrotra, S.; Miller, R.; Milhous, W.; Goins, D. K.; Venkatesan, S.; Wyandt, C.; Khan, I.; Avery, B. A. J. Med. Chem. 1995, 38, 5038.
32. 32. Jung, M.; Lee, S. Heterocycles 1997, 45, 1055.
33. 33. Jefford, C. W.; Velarde, J. A.; Bernardinelli, G.; Bray, D. H.; Warhurst, D. C.; Milhous, W. K. Helv. Chim. Acta 1993, 76, 2775.