Abstract
There have been few reports on synthetic methods for cis-1,2-diaminocyclohexane bearing a third ring substituent. Starting from 3-cyclohexenecarboxylic acid, we developed efficient methods for synthesizing the 3,4-diaminocyclohexanecarboxylic acid derivatives 2-5. We also evaluated their anti-Xa and anticoagulant activities. Among the compounds, acid 2a and amide 2b exhibited the most potent in vitro anti-fXa activity, indicating that the position and stereochemistry of a polar functional group on the cyclohexane ring greatly affected the in vitro anti-fXa activity.
MeSH terms
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Animals
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Anticoagulants / pharmacology
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Antithrombin III / chemistry
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Antithrombin III / pharmacology
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Benzothiazoles / chemical synthesis*
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Benzothiazoles / pharmacology
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Blood Coagulation / drug effects
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Carboxylic Acids / chemistry
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Carboxylic Acids / pharmacology*
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Chemistry, Pharmaceutical / methods
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Cyclohexanes / chemistry
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Cyclohexylamines / chemical synthesis*
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Cyclohexylamines / pharmacology
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Drug Design
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Factor Xa / chemistry
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Factor Xa Inhibitors*
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Inhibitory Concentration 50
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Models, Chemical
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Serine Proteinase Inhibitors / chemical synthesis
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Stereoisomerism
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Time Factors
Substances
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Anticoagulants
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Benzothiazoles
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Carboxylic Acids
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Cyclohexanes
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Cyclohexylamines
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Factor Xa Inhibitors
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Serine Proteinase Inhibitors
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Cyclohexane
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Antithrombin III
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Factor Xa