Abstract
The previously unknown stereoisomers 3, 4, ent-1, and ent-4 of the tris(pyrrolidinoindoline) alkaloids hodgkinsine (1) and hodgkinsine B (2) were prepared by stereocontrolled total synthesis. In each synthesis, a catalyst-controlled intramolecular Heck reaction was the key step in appending a third cis-pyrrolidinoindoline ring to a hexacyclic chimonanthine precursor. Results of the preliminary evaluation of these hodgkinsine stereoisomers in the tail flick and capsaicin pain models are reported.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkaloids / pharmacology
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Alkaloids / therapeutic use
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Analgesics, Non-Narcotic / chemical synthesis*
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Analgesics, Non-Narcotic / chemistry
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Analgesics, Non-Narcotic / pharmacology
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Analgesics, Non-Narcotic / therapeutic use
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Animals
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Disease Models, Animal
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Indoles / chemical synthesis*
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Indoles / chemistry
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Indoles / pharmacology
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Indoles / therapeutic use
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Mice
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Molecular Structure
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Pain / drug therapy
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Stereoisomerism
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Thermodynamics
Substances
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Alkaloids
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Analgesics, Non-Narcotic
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Indoles
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hodgkinsine