Abstract
The 2-methyleneoxetane analog 2 of orlistat (OLS, 1) has been synthesized and tested against porcine pancreatic lipase (PPL). Despite the loss of the carbonyl group, a potential site for hydrogen bonding interaction with the enzyme and the key element in the acylation by OLS, 2 has activity comparable to 1.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Ethers, Cyclic / chemical synthesis*
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Ethers, Cyclic / chemistry
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Ethers, Cyclic / pharmacology
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Heterocyclic Compounds, 1-Ring / chemical synthesis*
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Heterocyclic Compounds, 1-Ring / chemistry
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Heterocyclic Compounds, 1-Ring / pharmacology
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Lactones / chemical synthesis*
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Lactones / chemistry*
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Lactones / pharmacology
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Leucine / analogs & derivatives*
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Leucine / chemical synthesis
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Leucine / chemistry
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Leucine / pharmacology
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Lipase / antagonists & inhibitors*
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Molecular Conformation
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Molecular Structure
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Orlistat
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Pancreas / enzymology*
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Structure-Activity Relationship
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Swine
Substances
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Enzyme Inhibitors
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Ethers, Cyclic
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Heterocyclic Compounds, 1-Ring
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Lactones
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N-formyl-1-((3-hexyl-4-methylene-2-oxetanyl)methyl)dodecyl 2-amino-4-methylpentanoate
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Orlistat
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Lipase
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Leucine