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Volumn 9, Issue 1, 2003, Pages 282-290

Studies on mimicry of naturally occurring annonaceous acetogenins: Non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells

Author keywords

Annonaceous acetogenins; Asymmetric synthesis; Cytotoxicity; Natural products; Structure activity relationships

Indexed keywords

CYTOLOGY; ORGANIC ACIDS; TOXICITY; TUMORS;

EID: 0037415097     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390021     Document Type: Article
Times cited : (39)

References (41)
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    • 0034674356 scopus 로고    scopus 로고
    • Grée et al. published a synthetic endeavor aiming at similar targets: Y. L. Huérou, J. Doyon, R. Grée, J. Org. Chem. 1999, 64, 6782-6790. However, they only completed the construction of the two chiral centers adjacent to the ethereal links without introducing the butenolide moiety. In 2000 they reported the synthesis of a set of 16 simplified analogues with a ketolactone moiety instead of the usual butenolide one: S. Rodier, Y. L. Huérou, B. Renoux, J. Doyon, P. Renard, A. Pirre, J.-P. Gesson, R. Grée, Bioorg. Med. Chem. Lett. 2000, 10, 1373-1375. Koert et al. reported the design, synthesis and bioactivity of other analogues of annonaceous acetogenins: a) S. Hoppen, U. Emde, T Friedrich, L. Grubert, U. Koert, Angew. Chem. 2000, 112, 2184-2184; Angew. Chem. Int. Ed. 2000, 39, 2099-2102; S. Arndt, U. Emde, S. Bäurle, T. Friedrich, L. Grubert, U. Koert, Chem. Eur. J. 2001, 7, 993-1005.
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    • Grée et al. published a synthetic endeavor aiming at similar targets: Y. L. Huérou, J. Doyon, R. Grée, J. Org. Chem. 1999, 64, 6782-6790. However, they only completed the construction of the two chiral centers adjacent to the ethereal links without introducing the butenolide moiety. In 2000 they reported the synthesis of a set of 16 simplified analogues with a ketolactone moiety instead of the usual butenolide one: S. Rodier, Y. L. Huérou, B. Renoux, J. Doyon, P. Renard, A. Pirre, J.-P. Gesson, R. Grée, Bioorg. Med. Chem. Lett. 2000, 10, 1373-1375. Koert et al. reported the design, synthesis and bioactivity of other analogues of annonaceous acetogenins: a) S. Hoppen, U. Emde, T Friedrich, L. Grubert, U. Koert, Angew. Chem. 2000, 112, 2184-2184; Angew. Chem. Int. Ed. 2000, 39, 2099-2102; S. Arndt, U. Emde, S. Bäurle, T. Friedrich, L. Grubert, U. Koert, Chem. Eur. J. 2001, 7, 993-1005.
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    • 0001120253 scopus 로고    scopus 로고
    • Part of our synthetic endeavors of simplified annonaceous acetogenins described in this paper has been published as a communication: B.-B. Zeng, Y. Wu, Q. Yu, Y.-L. Wu, Y. Li, X.-G. Chen, Angew. Chem. 2000, 112, 2010-2013; Angew. Chem. Int. Ed. 2000, 39, 1934-1937.
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    • Zeng, B.-B.1    Wu, Y.2    Yu, Q.3    Wu, Y.-L.4    Li, Y.5    Chen, X.-G.6
  • 26
    • 0034596013 scopus 로고    scopus 로고
    • Part of our synthetic endeavors of simplified annonaceous acetogenins described in this paper has been published as a communication: B.-B. Zeng, Y. Wu, Q. Yu, Y.-L. Wu, Y. Li, X.-G. Chen, Angew. Chem. 2000, 112, 2010-2013; Angew. Chem. Int. Ed. 2000, 39, 1934-1937.
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    • Similar strategies have been employed in the total synthesis of natural acetogenins; see, e.g.: a) J. Marshall, H.-J. Jiang, J. Org. Chem. 1998, 63, 7066-7071; b) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057.
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    • Similar strategies have been employed in the total synthesis of natural acetogenins; see, e.g.: a) J. Marshall, H.-J. Jiang, J. Org. Chem. 1998, 63, 7066-7071; b) S. Hanessian, T. A. Grillo, J. Org. Chem. 1998, 63, 1049-1057.
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