Stereoselective synthesis and biological evaluation of 3,4-diaminocyclohexanecarboxylic acid derivatives as factor Xa inhibitors.
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Nagata T, Nagamochi M, Kobayashi S, Komoriya S, Yoshino T, Kanno H
Stereoselective synthesis and biological evaluation of 3,4-diaminocyclohexanecarboxylic acid derivatives as factor Xa inhibitors.
Bioorg Med Chem Lett. 2008 Aug 15;18(16):4587-92. doi: 10.1016/j.bmcl.2008.07.031. Epub 2008 Jul 15.
- PubMed ID
- 18675545 [ View in PubMed]
- 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.
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- Binding Properties
Drug Target Property Measurement pH Temperature (°C) N-((1R,2S)-2-(5-CHLORO-1H-INDOLE-2-CARBOXAMIDO)CYCLOHEXYL)-5-METHYL-4,5,6,7-TETRAHYDROTHIAZOLO[5,4-C]PYRIDINE-2-CARBOXAMIDE Coagulation factor X IC 50 (nM) 16 N/A N/A Details