Toosendanin: Synthesis of the AB-ring and investigations of its anti-botulinum properties (Part II)

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 3, 2010, Pages 1280-1287

  Nakai, Yuya ^a   Pellett, Sabine ^b   Tepp, William H ^b   Johnson, Eric A ^b   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF WISCONSIN   (United States)

Author keywords

Botulinum neurotoxins; Rat spinal cord cellular assay; Semi synthesis; Toosendanin

Indexed keywords

ACETAL; BOTULINUM TOXIN; LIMONOID; METHYL 7 (BENZYLOXY) 1 METHYL 2 OXO 4 [[2 (TRIMETHYLSILYL)ETHOXY]METHOXY]METHYL] 4A [[[2 (TRIMETHYLSILYL)ETHOXY]METHOXY]METHYL]DECAHYDRONAPHTHALENE 1 CARBOXYLATE; METHYL 7 (BENZYLOXY) 4 HYDROXY 1 METHYL 2 OXO 4A[[[2 (TRIMETHYLSILYL)ETHOXY]METHOXY]METHYL]DECAHYDRONAPHTHALENE 1 CARBOXYLATE; TOOSENDANIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CHINESE MEDICINE; CONTROLLED STUDY; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; RAT; SPINAL CORD;

ANIMALS; BOTULINUM TOXIN TYPE A; BOTULISM; CELL CULTURE TECHNIQUES; CLOSTRIDIUM BOTULINUM; DRUGS, CHINESE HERBAL; HUMANS; RATS; SPINAL CORD;

ANIMALIA; RATTUS;

EID: 75149115102     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.12.030     Document Type: Article

References (40)

1. Johnson E.A., and Bradshaw M. Toxicon 39 (2001) 1703
2. Schantz E.J., and Johnson E.A. Microbiol. Rev. 56 (1992) 80
3. Singh B.R. Nat. Struct. Biol. 7 (2000) 617
4. Willis B., Eubanks L.M., Dickerson T.J., and Janda K.D. Angew. Chem., Int. Ed. 47 (2008) 8360
5. Dickerson T.J., and Janda K.D. ACS Chem. Biol. 1 (2006) 359
6. Simpson L. Annu. Rev. Pharmacol. Toxicol. 44 (2004) 167
7. Nakatani M. Heterocycles 50 (1999) 595
8. Carpinella C., Ferrayoli C., Valladares G., Defago M., and Palacios S. Biosci. Biotechnol. Biochem. 66 (2002) 1731
9. Xie Y.S., Fields P.G., Isman M.B., Chen W.K., and Zhang X. J. Stored Prod. Res. 31 (1995) 259
10. Akhtar Y., and Isman M.B. J. Chem. Ecol. 29 (2003) 1853
11. Carpinella M.C., Defago M.T., Valladares G., and Palacios S.M. J. Agric. Food Chem. 51 (2003) 369
12. Zhou J.-B., Minami Y., Yagi F., Tadera K., and Nakatani M. Heterocycles 45 (1997) 1781
13. Zou J., Miao W., Ding F., Meng J., Ye H., Jia G., He X., Sun G., and Li P. J. Tradit. Chin. Med. 5 (1985) 29
14. Li P.Z., Zhou J., Miao W.Y., Ding F.H., Meng J.-Y., Ye H.J., Jia G.R., and He X.Y. Chin. Tradit. Herb Drugs 17 (1982) 28
15. Fischer A., Nakai Y., Eubanks L.M., Clancy C.M., Tepp W.H., Pellett S., Dickerson T.J., Johnson E.A., Janda K.D., and Montal M. Proc. Natl. Acad. Sci. U.S.A. 106 (2009) 1330
16. Čapcová K., Yoneda Y., Dickerson T.J., and Janda K.D. Bioorg. Med. Chem. Lett. 17 (2007) 6463
17. Eubanks L.M., Hixon M.S., Jin W., Hong S., Clancy C.M., Tepp W.H., Baldwin M.R., Malizio C.J., Goodnough M.C., Barbieri J.T., Johnson E.A., Boger D.L., Dickerson T.J., and Janda K.D. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 2602
18. Silvaggi N.R., Boldt G.E., Hixon M.S., Kennedy J.P., Tzipori S., Janda K.D., and Allen K.N. ACS Chem. Biol. 14 (2007) 533
19. Boldt G.E., Eubanks L.M., and Janda K.D. Chem. Commun. (2006) 3063
20. Boldt G.E., Kennedy J.P., and Janda K.D. Org. Lett. 8 (2006) 1729
21. Wender P.A., Verma V.A., Paxton T.J., and Pillow T.H. Acc. Chem. Res. 41 (2008) 40
22. Nakai Y., Tepp W.H., Dickerson T.J., Johnson E.A., and Janda K.D. Bioorg. Med. Chem. 17 (2009) 1152
23. Jones J.B., and Dodds D.R. Can. J. Chem. 65 (1987) 2397
24. Nicolaou K.C., Follmann M., Roecker A.J., and Hunt K.W. Angew. Chem., Int. Ed. 41 (2002) 2103
25. Ghosh S., Rivas F., Fischer D., González M.A., and Theodorakis E.A. Org. Lett. 6 (2004) 941
26. Ziegler F.E., Hwang K.-J., Kadow J.F., Klein S.I., Pati U.K., and Wang T.-F. J. Org. Chem. 51 (1986) 4573
27. Crabtree S.R., Alex Chu W.L., and Mander L.N. Synlett (1990) 169
28. Fairweather K.A., and Mander L.N. Org. Lett. 8 (2006) 3395
29. Rodeschini V., Van de Weghe P., Salomon E., Tarnus C., and Eustache J. J. Org. Chem. 70 (2005) 2409
30. Nicolaus K.C., Sasmal P.K., Roecker A.J., Sun X.-W., Mandal S., and Converso A. Angew. Chem., Int. Ed. 44 (2005) 3443
31. Rodeschini V., Boiteau J.-G., Van de Weghe P., Tarnus C., and Eustache E. J. Org. Chem. 69 (2004) 357
32. Miyashita M., Suzuki T., Hoshino M., and Yoshikoshi A. Tetrahedron 53 (1997) 12469
33. Miyashita M., Suzuki T., and Yoshikoshi A. Tetrahedron Lett. 28 (1987) 4293
34. Smith III A.B., Davulcu A.H., Cho Y.S., Ohmoto K., Kürti L., and Ishiyama H. J. Org. Chem. 72 (2007) 4596
35. Nicolaus K.C., Jennings M.P., and Dagneau P. Chem. Commun. (2002) 2480
36. De Mico A., Margarita R., Parlanti L., Vescovi A., and Piancatelli G. J. Org. Chem. 62 (1997) 6974
37. Pellett S., Tepp W.H., Clancy C.M., Borodic G.E., and Johnson E.A. FEBS Lett. 581 (2007) 4803
38. Malizio C.J., Goodnough M.C., and Johnson E.A. Methods Mol. Biol. 145 (2000) 27
39. Hatheway C.L. Botulism. Laboratory Diagnosis of Infectious Diseases. Principles and Practise (1988), Springer, New York 111-113
40. Schantz E.J., and Kautter D.A. J. Assoc. Off. Anal. Chem. 61 (1978) 96