Synthesis of functionalized cinnamaldehyde derivatives by an oxidative heck reaction and their use as starting materials for preparation of Mycobacterium tuberculosis 1-deoxy-d-xylulose-5-phosphate reductoisomerase inhibitors

Journal of Organic Chemistry

Volumn 76, Issue 21, 2011, Pages 8986-8998

  Nordqvist, Anneli ^a   Björkelid, Christofer ^b   Andaloussi, Mounir ^a   Jansson, Anna M ^b   Mowbray, Sherry L ^b   Karlén, Anders ^a   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLBORONIC ACIDS; CINNAMALDEHYDE DERIVATIVES; FUNCTIONALIZED; HECK REACTIONS; MYCOBACTERIUM TUBERCULOSIS; ONE STEP; REDUCTOISOMERASE; UNSATURATED ALDEHYDES;

ALDEHYDES; PALLADIUM COMPOUNDS;

SYNTHESIS (CHEMICAL);

1 DEOXY XYLULOSE 5 PHOSPHATE REDUCTOISOMERASE INHIBITOR; 3 (4 BENZOYLPHENYL)ACRYLALDEHYDE; 3 (4 BROMOPHENYL)ACRYLALDEHYDE; 3 (4 CHLOROPHENYL)ACRYLALDEHYDE; 3 (4 PHENOXYPHENYL)ACRYLALDEHYDE; 3 (5 (TERT BUTYL) 2 METHOXYPHENYL)ACRYLALDEHYDE; 3 (BENZO[D][1,3]DIOXOL 5 YL)ACRYLALDEHYDE; 3 (BENZOFURAN 2 YL)ACRYLALDEHYDE; 3 (DIBENZO[B,D]FURAN 4 YL)ACRYLALDEHYDE; 3 (NAPHTHALEN 2 YL)ACRYLALDEHYDE; 3 (P TOLYL)ACRYLALDEHYDE; 3 (THIOPHEN 3 YL)ACRYLALDEHYDE; 4 (NAPHTHALEN 2 YL)BUT 3 EN 2 ONE; CINNAMALDEHYDE DERIVATIVE; DIETHYL(1 (BENZOFURAN 2 YL) 3 OXOPROPYL)PHOSPHONATE; DIETHYL[1 (4 BROMOPHENYL) 3 OXOPROPYL]PHOSPHONATE; DIETHYL[1 (BENZO[D][1,3]DIOXOL 5 YL) 3 [N (BENZYLOXY)ACETAMIDO]PROPYL]PHOSPHONATE; DIETHYL[1 (BENZO[D][1,3]DIOXOL 5 YL) 3 OXOPROPYL]PHOSPHONATE; DIETHYL[1 (BENZOFURAN 2 YL) 3 [N (BENZYLOXY)ACETAMIDO]PROPYL]PHOSPHONATE; DIETHYL[1 (NAPHTHALEN 2 YL) 3 OXOPROPYL]PHOSPHONATE; DIETHYL[1 [(1,10 BIPHENYL) 4 YL] 3 [N (BENZYLOXY)ACETAMIDOPROPYL]PHOSPHONATE; DIETHYL[1 [(1,10 BIPHENYL) 4 YL] 3 OXOPROPYL]PHOSPHONATE; DIETHYL[3 [N (BENZYLOXY)ACETAMIDO] 1 (4 BROMOPHENYL)PROPYL]PHOSPHONATE; DIETHYL[3 [N (BENZYLOXY)ACETAMIDO] 1 (NAPHTHALEN 2 YL)PROPYL]PHOSPHONATE; FOSMIDOMYCIN; ISOMERASE INHIBITOR; PALLADIUM; TERT BUTYL (4 (3 OXOPROP 1 EN 1 YL)PHENYL)CARBAMATE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION; IC 50; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; OXIDATION; ROOM TEMPERATURE; SUBSTITUTION REACTION;

ACROLEIN; ALDOSE-KETOSE ISOMERASES; ANTITUBERCULAR AGENTS; CATALYSIS; FOSFOMYCIN; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MULTIENZYME COMPLEXES; MYCOBACTERIUM TUBERCULOSIS; OXIDATION-REDUCTION; OXIDOREDUCTASES; PALLADIUM; PROTEIN BINDING;

EID: 80055098225     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201715x     Document Type: Article

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