“Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue

“Clicktophycin-52”: A Bioactive Cryptophycin-52 Triazole Analogue

An endocyclic trans-amide linkage within the macrocyclic antitumor agent cryptophycin-52 was replaced by a 1,4-disubstituted 1H-1,2,3-triazole ring. Macrocyclisation of the triazole analogue was accomplished by macrolactamization as well as by Cu(I)-mediated “click”-cyclization. Compared to cryptoph...

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Veröffentlicht in:Organic letters 2010-03, Vol.12 (5), p.1064-1067
Hauptverfasser: Nahrwold, Markus, Bogner, Tobias, Eissler, Stefan, Verma, Spart, Sewald, Norbert
Format: Artikel
Sprache:eng
Schlagworte:
Cell Line, Tumor
Depsipeptides - chemistry
Depsipeptides - pharmacology
Humans
Inhibitory Concentration 50
Lactams - chemistry
Lactams - pharmacology
Lactones - chemistry
Lactones - pharmacology
Triazoles - chemistry
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Zusammenfassung:An endocyclic trans-amide linkage within the macrocyclic antitumor agent cryptophycin-52 was replaced by a 1,4-disubstituted 1H-1,2,3-triazole ring. Macrocyclisation of the triazole analogue was accomplished by macrolactamization as well as by Cu(I)-mediated “click”-cyclization. Compared to cryptophycin-52, in vitro cytotoxicity of “clicktophycin-52” against the multidrug resistant human cancer cell line KB-V1 is only slightly reduced.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1000473