Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 19, 2010, Pages 7101-7112

  Sun, Liang ^a   Veith, Jean M ^b   Pera, Paula ^b   Bernacki, Ralph J ^b   Ojima, Iwao ^a  

^a STONY BROOK UNIVERSITY   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

Alkaloid; Anticancer; Cytotoxicity; Molecular modeling; Paclitaxel mimics; REDORE Taxol; Tubulin

Indexed keywords

1 (TERT BUTOXYCARBONYL) 2 [(2,6 DIETHENYLPHENYL)HYDROXYMETHYL] 4 TRIISOPROPYLSILOXYPYRROLIDINE; 1 (TERT BUTOXYCARBONYL) 5 [HYDROXY(2 ETHENYL 6 HYDROXYMETHYLPHENYL)METHYL] 3 TRIISOPROPYLSILOXY PYRROLIDINE; 10 (ACETOXYMETHYL) 11 BENZOYLOXY 2 HYDROXY 2,3,11,11A TETRAHYDRO 1H BENZO[D]PYRROLO[1,2 A]AZEPIN 5(6H)ONE; 10 (ACETOXYMETHYL) 11 BENZOYLOXY 2 TRIISOPROPYLSILOXY 2,3,11,11A TETRAHYDRO 1H BENZO[D]PYRROLO[1,2 A]AZEPIN 5(6H)ONE; 10 ACETOXY 9 ACETOXYMETHYL 2 TRIISOPROPYLSILOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 10 ACETOXY 9 METHOXYCARBONYL 2 TRIISOPROPYLSILOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLINE 5 ONE; 10 ACETOXY 9 METHOXYMETHOXY METHYL 2 TRIISOPROPYLSILOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 10 BENZOYLOXY 2 HYDROXY 9 PENT 4 ENOYLOXYMETHYL 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 10 BENZOYLOXY 2 TRIISOPROPYLSILOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 10 BENZOYLOXY 5 OXO 9 PENT 4 ENOYLOXYMETHYL 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 2 YL 4'(2 ALLYLOXYPHENYL) 3' BENZOYL 2' (4 METHOXYPHENYL)OXAZOLIDINE 5 CARBOXYLATE; 10 BENZOYLOXY 9 (TERT BUTYLDIMETHYLSILOXYMETHYL) 2 TRIISOPROPYLSILOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 10 BENZOYLOXY 9 PENT 4 ENOYLOXYMETHYL 2 TRIISOPROPYLSILOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 10 HYDROXY 9 HYDROXYMETHYL 2 TRIISOPROPYLSILOXY 2,3,10,10A TETRAHYDRO 1H PYRROLO [1,2 B]ISOQUINOLIN 5 ONE; 11 ACETOXY 10 (METHOXYMETHOXYMETHYL) 2 TRIISOPROPYLSILOXY 2,3,11,11A TETRA HYDRO 1H BENZO[D]PYRROLO[1,2 A]AZEPIN 5(6H)ONE; 11 ACETOXY 10 (METHOXYMETHOXYMETHYL) 2 TRIISOPROPYLSILOXY 2,3,11,11A TETRAHYDRO 1H BENZO[D]PYRROLO[1,2 A]AZEPIN 5(6H)ONE; 11 HYDROXY 10 (METHOXYMETHOXYMETHYL) 2 TRIISOPROPYLSILOXY 2,3,11,11A TETRAHYDRO 1H BENZO[D]PYRROLO[1,2 A]AZEPIN 5(6H)ONE; 2 (4 METHOXYPHENYL) 3 BENZOYL 4 PHENYLOXAZOLIDINE 5 CARBOXYLIC ACID; 2 [ACETOXY(2 METHOXYMETHOXYMETHYL 6 ETHENYLPHENYL)METHYL] 1 (TERT BUTOXYCARBONYL) 3 TRIISOPROPYLSILOXYPYRROLIDINE; 4 (2 ALLYLOXYPHENYL) 3 BENZOYL 2 (4 METHOXYPHENYL)OXAZOLIDINE 5 CARBOXYLIC ACID; 5 [ACETOXY(2 ACETOXYMETHYL 6 ETHENYL PHENYL)METHYL] 1 (TERT BUTOXYCARBONYL) 3 TRIISOPROPYLSILOXYPYRROLIDINE; 5 [ACETOXY(2 ALLYL 6 METHOXYMETHOXYMETHYLPHENYL)METHYL] 1 (TERT BUTOXYCARBONYL) 3 TRIISOPROPYLSILOXYPYRROLIDINE; 5 [ACETOXY(2,6 DIETHENYLPHENYL)METHYL] 1 (TERTBUTOXYCARBONYL) 3 TRIISOPROPYLSILOXYPYRROLIDINE; 9 (TERT BUTYLDIMETHYLSILOXYMETHYL) 10 HYDROXY 2 TRIISOPROPYLSILOXY 2,3,10,10A TETRAHYDRO 1H PYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 9 ACETOXYMETHYL 10 BENZOYLOXY 2 HYDROXYL 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 9 ACETOXYMETHYL 10 BENZOYLOXY 2 TRIISOPROPYLSILOXY 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 5 ONE; 9 ACETOXYMETHYL 10 BENZOYLOXY 5 OXO 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 2 YL 3' BENZOYL 2' (4 METHOXY PHENYL) 4' PHENYLOXAZOLIDINE 5' CARBOXYLATE; 9 ACETOXYMETHYL 10 BENZOYLOXY 5 OXO 1,2,3,5,10,10A HEXAHYDROPYRROLO[1,2 B]ISOQUINOLIN 2 YL 3' BENZOYLAMINO 2' HYDROXY 3' PHENYLPROPANOATE; ANTINEOPLASTIC ALKALOID; PACLITAXEL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CANCER CELL CULTURE; CANCER RESISTANCE; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MOLECULAR MODEL; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; TUMOR GROWTH;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; COMPUTATIONAL BIOLOGY; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR DYNAMICS SIMULATION; MOLECULAR MIMICRY; PACLITAXEL; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956652112     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.07.069     Document Type: Article

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