Synthesis of all low-energy stereoisomers of the tris(pyrrolidinoindoline) alkaloid hodgkinsine and preliminary assessment of their antinociceptive activity

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 7909-7914

  Kodanko, Jeremy J ^a   Hiebert, Sheldon ^a   Peterson, Emily A ^a   Sung, Leonard ^a   Overman, Larry E ^a   Linck, Viviane De Moura ^b   Goerck, Greice Catrine ^b   Amador, Tânia Alves ^b   Leal, Mirna Bainy ^b   Elisabetsky, Elaine ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CAPSAICIN PAIN MODELS; HECK REACTION; PYRROLIDINOINDOLINE; STEREOISOMERS;

CATALYSTS; ISOMERS; MATHEMATICAL MODELS; SYNTHESIS (CHEMICAL);

STEREOCHEMISTRY;

ALKALOID; ANTINOCICEPTIVE AGENT; CHIMONANTHINE; CYCLOALKENE; HODGKINSINE; HODGKINSINE B; INDOLE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CATALYST; CIS ISOMER; CYCLIZATION; DRUG SYNTHESIS; HECK REACTION; MOUSE; NONHUMAN; PAIN; QUANTUM YIELD; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; ANALGESICS, NON-NARCOTIC; ANIMALS; DISEASE MODELS, ANIMAL; INDOLES; MICE; MOLECULAR STRUCTURE; PAIN; STEREOISOMERISM; THERMODYNAMICS;

EID: 35348908937     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7013643     Document Type: Article

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26. Naloxone reversibility was not studied for ent-1.
27. General experimental procedures can be found in the Supporting Information.