Synthesis and biological properties of cylindramide derivatives: Evidence for calcium-dependent cytotoxicity of tetramic acid lactams

ChemBioChem

Volumn 9, Issue 15, 2008, Pages 2474-2486

  Cramer, Nicolai ^a   Helbig, Sarah ^a   Baro, Angelika ^a   Laschat, Sabine ^a   Diestel, Randi ^b   Sasse, Florenz ^b   Mathieu, Daniel ^c   Richter, Christian ^c   Kummerlöwe, Grit ^d   Luy, Burkhard ^d   Schwalbe, Harald ^c  

^a UNIVERSITY OF STUTTGART   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^c GOETHE UNIVERSITY   (Germany)

^d TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Biological activity; Cyclization; Macrolactam; NMR spectroscopy; Olefination

Indexed keywords

1 (DIMETHOXYMETHYL) 2 (3 IODOPROP 2 YNYL)CYCLOPENTANE; 1 (DIMETHOXYMETHYL) 2 PROP 2 YNYLCYCLOPENTANE; 1 (DIMETHOXYMETHYL) 3 (3 IODOPROP 2 YNYL)CYCLOPENTANE; 10,15 DIHYDROXY 1,7,8,9,10,11,12,16,17,19A,20,21,22,22A TETRADECAHYDRO 11,14 METHANOCYCLOPENTA[1,6]DIAZACYCLOHENICOSINE 6,13,23 TRIONE DERIVATIVE; 2 (DIMETHOXYMETHYL) 3 [3 (TRIMETHYLSILYL)PROP 2 YNYL]CYCLOPENTANONE; ALTERAMIDE; CALCIUM; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; CYLINDRAMIDE DERIVATIVE; CYTOTOXIC AGENT; DISCODERMIDE; LACTAM DERIVATIVE; METHYL 10 [[TERT BUTYL(DIMETHYL)SILYL]OXY] 6,13,15 TRIOXO 1,6,7,8,9,10,11,12,13,14,15,16,17,19A,20,21,22,22A OCTADECAHYDROCYCLOPENTA[1,6]DIAZACYCLOHENICOSIN 11 CARBOXYLIC ACID; METHYL 10 [[TERT BUTYL(DIMETHYL)SILYL]OXY] 6,13,15 TRIOXO 2,3 DIDEHYDRO 1,6,7,8,9,10,11,12,13,14,15,16,17,19A,20,21,22,22A OCTADECAHYDROCYCLOPENTA[1,6]DIAZACYCLOHENICOSIN 11 CARBOXYLIC ACID; METHYL 10 HYDROXY 6,13,15 TRIOXO 1,6,7,8,9,10,11,12,13,14,15,16,17,19A,20,21,22,22A OCTADECAHYDROCYCLOPENTA[1,6]DIAZACYCLOHENICOSIN 11 CARBOXYLIC ACID; METHYL 2 AZIDO 3 [TERT BUTYL(DIMETHYL)SILANYLOXY] 5 [[6 [2 (DIMETHOXYMETHYL)CYCLOPENTYL]HEX 2 EN 4 YNOYL]AMINO]PENTANOIC ACID; METHYL 2 AZIDO 3 O [TERT BUTYL(DIMETHYL)SILYL] 5 [6 [2 (DIMETHOXYMETHYL)CYCLOPENTYL]HEXA 2,4 DIENYL]AMIDOPENTANOIC ACID; METHYL 2 AZIDO 3 O [TERT BUTYL(DIMETHYL)SILYL] 5 [6 [2 [4 (2,2 DIMETHYL 4 OXO 4H 1,3 DIOXIN 6 YL)BUT 1 ENYL]CYCLOPENTYL]HEX 2 EN YNYL]AMINOPENTANOIC ACID; METHYL 2 AZIDO 3 O [TERT BUTYL(DIMETHYL)SILYL] 5 [[6 [2 [4 (2,2 DIMETHYL 4 OXO 4H 1,3 DIOXIN 6 YL)BUT 1 ENYL]CYCLOPENTYL]HEXA 2,4 DIENYL]AMIDO]PENTANOIC ACID; POLYACRYLONITRILE; TETRAMIC ACID DERIVATIVE; TRIBUTYL [3 [2 (DIMETHOXYMETHYL)CYCLOPENTYL]PROP 1 ENYL]STANNANE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CELL VACUOLE; CONTROLLED STUDY; CORRELATION ANALYSIS; CYCLIZATION; CYTOTOXICITY; DRUG SYNTHESIS; ENDOPLASMIC RETICULUM; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; OLEFINATION; PRIORITY JOURNAL; SONOGASHIRA REACTION; STILLE REACTION; TUMOR CELL LINE;

AMIDES; ANIMALS; CALCIUM; CELL LINE, TUMOR; CELL SURVIVAL; CYCLOPENTANES; HUMANS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; PYRROLIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 54349104013     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200800284     Document Type: Article

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