Total Synthesis and Biological Evaluation of Tubulysin Analogues

Journal of Organic Chemistry

Volumn 81, Issue 21, 2016, Pages 10302-10320

  Colombo, Raffaele ^a,c   Wang, Zhiyong ^a   Han, Junyan ^a   Balachandran, Raghavan ^a   Daghestani, Hikmat N ^a,b   Camarco, Daniel P ^b   Vogt, Andreas ^b   Day, Billy W ^a,b   Mendel, David ^c   Wipf, Peter ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL DEATH;

ANTI-PROLIFERATIVE; ANTI-PROLIFERATIVE ACTIVITIES; ANTIMITOTIC AGENTS; BIOLOGICAL EVALUATION; FUNCTIONALIZATIONS; ORDERS OF MAGNITUDE; SECOND-GENERATION SYNTHESIS; TERMINAL MODIFICATIONS;

BIOACTIVITY;

3 [ 1 [ 2 [ 1 CETOXY 4 METHYL 3 [ 3 METHYL 2 ( 1 METHYLPIPERIDINE 2 CARBOXAMIDO)PENTANAMIDO]PENTYL]THIAZOLE 4 CARBONYL]INDOLIN 2 YL] 2 METHYLPROPANOIC ACID 2,2,2 TRIFLUOROACETATE; 3 [N,3 DIMETHYL 2 ( 1 METHYLPIPERIDINE 2 CARBOXAMIDO)PENTANAMIDO] 1 [4 [( 5 HYDRAZINYL 4 METHYL 5 OXO 1 PHENYLPENTAN 2 YL)CARBAMOYL]THIAZOL 2 YL] 4 METHYLPENTYL ACETATE TRIFLUOROACETATE; 4 [ 2 [ 1 ACETOXY 3 [N,3 DIMETHYL 2 ( 1 METHYLPIPERIDINE 2 CARBOXAMIDO)PENTANAMIDO] 4 METHYLPENTYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYL 5 PHENYLPENT 2 ENOIC ACID 2,2,2 TRIFLUOROACETATE; 4 [ 2 [ 1 ACETOXY 3 [N,3 DIMETHYL 2 ( 1 METHYLPYRROLIDINE 2 CARBOXAMIDO)PENTANAMIDO] 4 METHYLPENTYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYL 5 PHENYLPENT 2 ENOIC ACID 2,2,2 TRIFLUOROACETATE; 4 [ 2 [3 [N,3 DIMETHYL 2 ( 1 METHYLPIPERIDINE 2 CARBOXAMIDO)BUTANAMIDO] 4 METHYLPENTYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYL 5 PHENYLPENT 2 ENOIC ACID 2,2,2 TRIFLUOROACETATE; 4 [2 [ 1 ACETOXY 3 [N,3 DIMETHYL 2 ( 1 METHYLPIPERIDINE 2 CARBOXAMIDO)PENTANAMIDO] 4 METHYLPENTYL] THIAZOLE 4 CARBOXAMIDO] 2 METHYL 5 PHENYLPENTANOIC ACID TRIFLUOROACETATE; 4 [2 [ 3 [N,3 DIMETHYL 2 (1 METHYLPIPERIDINE 2 CARBOXAMIDO)PENTANAMIDO] 4 METHYLPENTYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYL 5 PHENYLPENT 2 ENOIC ACID 2,2,2 TRIFLUOROACETATE; 4 [2 [1 ACETOXY 4 METHYL 3 [ 3 METHYL 2 (1 METHYLPIPERIDINE 2 CARBOXAMIDO)PENTANAMIDO]PENTYL] THIAZOLE 4 CARBOXAMIDO] 5 (2 IODOPHENYL) 2 METHYLPENTANOIC ACID 2,2,2 TRIFLUOROACETATE; 5 [(1,1' BIPHENYL) 2 YL] 4 [ 2 [ 1 ACETOXY 4 METHYL 3 [ 3 METHYL 2 ( 1 METHYLPIPERIDINE 2 CARBOXAMIDO) PENTANAMIDO]PENTYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYLPENTANOIC ACID 2,2,2 TRIFLUOROACETATE; ALLYL 4 [2 [1 ACETOXY 3 [N,3 DIMETHYL 2 (1 METHYLPIPERIDINE 2 CARBOXAMIDO)PENTANAMIDO] 4 METHYLPENTYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYL 5 PHENYLPENTANOATE; ANTINEOPLASTIC AGENT; MONOMETHYL AURISTATINS D; MONOMETHYL AURISTATINS E; N 14 DESACETOXYTUBULYSIN; PACLITAXEL; TUBULYSIN DERIVATIVE; UNCLASSIFIED DRUG; VINCRISTINE; N14-DESACETOXYTUBULYSIN H; OLIGOPEPTIDE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DESILYLATION; DIASTEREOISOMER; DRUG ACETYLATION; DRUG CONJUGATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HELA CELL LINE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROGENATION; LIPOPHILICITY; MITOSIS INHIBITION; PROTON NUCLEAR MAGNETIC RESONANCE; SONOGASHIRA REACTION; STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; MITOSIS; SYNTHESIS;

APOPTOSIS; CARBON-13 MAGNETIC RESONANCE SPECTROSCOPY; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; MITOSIS; OLIGOPEPTIDES; PROTON MAGNETIC RESONANCE SPECTROSCOPY;

EID: 84994614181     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.6b01314     Document Type: Article

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