Regioselective hydrostannation of diarylalkynes directed by a labile ortho bromine atom: An easy access to stereodefined triarylolefins, hybrids of combretastatin A-4 and isocombretastatin A-4

European Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2010, Pages 3617-3626

  Rasolofonjatovo, Evelia ^a   Provot, Olivier ^a   Hamze, Abdallah ^a   Bignon, Jérome ^b   Thoret, Sylviane ^b   Brion, Jean Daniel ^a   Alami, Mouâd ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

Alkyne; Combretastatin; Hydrostannation; Olefin; Ortho directing effect; Palladium

Indexed keywords

1 [1 (2 BROMO 3,4,5 TRIMETHOXYPHENYL) 2 (4METHOXYPHENYL)VINYL] 4 METHOXYBENZENE; 1 [1,2 BIS(4 METHOXY 3 (METHOXYMETHOXY)PHENYL]VINYL] 2 BROMO 3,4,5 TRIMETHOXYBENZENE; 1 IODO 1,2 BIS(4 METHOXYPHENYL)ETHENE; 1 METHOXY 4 [2 (4 METHOXYPHENYL) 1 (3,4,5 TRIMETHOXYPHENYL)VINYL]BENZENE; 1,2,3 TRIMETHOXY 5 [1 (4 METHOXYPHENYL) 2 (3,4,5 TRIMETHOXYPHENYL)VINYL]BENZENE; 2 [1 (2 BROMO 3,4,5 TRIMETHOXYPHENYL) 2 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL]VINYL]NAPHTHALENE; 2 BROMO 1 [1 (3 FLUORO 4 METHOXYPHENYL) 2 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL]VINYL] 3,4,5 TRIMETHOXYBENZENE; 2 BROMO 1 [1 IODO 2 (3,4,5 TRIMETHOXYPHENYL)VINYL] 4 METHOXYBENZENE; 2 BROMO 3,4,5 TRIMETHOXY 1 [2 (4 METHOXYPHENYL) ETHYNYL]BENZENE; 2 BROMO 3,4,5 TRIMETHOXY 1 [2 [4 METHOXY 3 (METHOXYMETHOXY) PHENYL] 1 4 TOLYLVINYL]BENZENE; 2 METHOXY 5 [2 (4 METHOXYPHENYL) 1 (3,4,5 TRIMETHOXYPHENYL)VINYL]PHENOL; 2 METHOXY 5 [2 (NAPHTHALEN 2 YL) 2 (3,4,5 TRIMETHOXYPHENYL)VINYL]PHENOL; 2 METHOXY 5 [2 4 TOLYL 2 (3,4,5 TRIMETHOXYPHENYL)VINYL]PHENOL; 4 [2 (2 BROMO 3,4,5 TRIMETHOXYPHENYL)ETHYNYL] 1 METHOXY 2 (METHOXYMETHOXY)BENZENE; 5 [1 (2 BROMO 4 METHOXYPHENYL) 2 (3,4,5 TRIMETHOXYPHENYL)VINYL] 1,2,3 TRIMETHOXYBENZENE; 5 [1,2 BIS(4 METHOXYPHENYL)VINYL] 1,2,3 TRIMETHOXYBENZENE; 5 [2 (3 FLUORO 4 METHOXYPHENYL) 2 (3,4,5 TRIMETHOXYPHENYL)VINYL] 2 METHOXYPHENOL; 5 [2 (3 HYDROXY 4 METHOXYPHENYL) 2 (3,4,5 TRIMETHOXYPHENYL)VINYL] 2 METHOXYPHENOL; [1 (2 BROMO 3,4,5 TRIMETHOXYPHENYL) 2 (4 METHOXYPHENYL) VINYL]TRIBUTYLSTANNANE; [1 (2 BROMO 3,4,5 TRIMETHOXYPHENYL) 2 [4 METHOXY 3 (METHOXYMETHOXY)PHENYL]VINYL]TRIBUTYLSTANNANE; [1 (2 BROMO 4 METHOXYPHENYL) 2 (3,4,5 TRIMETHOXYPHENYL) VINYL]TRIBUTYLSTANNANE; [5 [2 (2 BROMO 3,4,5 TRIMETHOXYPHENYL) 2 (4 METHOXYPHENYL)VINYL] 2 METHOXYPHENOXY]TERT BUTYLDIMETHYLSILANE; [5 [2 (2 BROMO 3,4,5 TRIMETHOXYPHENYL) 2 (TRIBUTYLSTANNYL)VINYL] 2 METHOXYPHENOXY] TERT BUTYLDIMETHYLSILANE; [5 [2 (2 BROMO 3,4,5 TRIMETHOXYPHENYL) 2 IODOVINYL] 2 METHOXYPHENOXY] TERT BUTYLDIMETHYLSILANE; [5 [2 (2 BROMO 3,4,5 TRIMETHOXYPHENYL)ETHYNYL] 2 METHOXYPHENOXY] TERT BUTYLDIMETHYLSILANE; ALKENE DERIVATIVE; ANTINEOPLASTIC AGENT; COMBRETASTATIN A4; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ATOM; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYBRID; STRUCTURE ACTIVITY RELATION;

ALKENES; ALKYNES; ANIMALS; ANTINEOPLASTIC AGENTS; BROMINE; CELL LINE, TUMOR; CELL PROLIFERATION; CHLOROPHENOLS; HUMANS; ORGANOTIN COMPOUNDS; PEPTIDES, CYCLIC; STEREOISOMERISM; STILBENES; SUBSTRATE SPECIFICITY;

EID: 77955551128     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.05.007     Document Type: Article

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