Cation-pi interactions at the active site of factor Xa: dramatic enhancement upon stepwise N-alkylation of ammonium ions.

Salonen LM; Bucher C; Banner DW; Haap W; Mary JL; Benz J; Kuster O; Seiler P; Schweizer WB; Diederich F

doi:10.1002/anie.200804695

Cation-pi interactions at the active site of factor Xa: dramatic enhancement upon stepwise N-alkylation of ammonium ions.

Haap W ,

Benz J ,

Affiliations

1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich, Switzerland.
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Salonen LM¹
(1 author)

ORCIDs linked to this article

Salonen LM | 0000-0001-8194-6014

Angewandte Chemie (International ed. in English), 01 Jan 2009, 48(4):811-814
https://doi.org/10.1002/anie.200804695 PMID: 19101972

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Articles referenced by this article (48)

Title not supplied
AUTHOR UNKNOWN
Oral, direct factor Xa inhibitors in development for the prevention and treatment of thromboembolic diseases.
Turpie AG
Arterioscler Thromb Vasc Biol, (6):1238-1247 2007
MED: 17379841
New oral Xa and IIa inhibitors: updates on clinical trial results.
Haas S
J Thromb Thrombolysis, (1):52-60 2007
MED: 17965837
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AUTHOR UNKNOWN
Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3- [4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene- 2-carboxamide (BAY 59-7939): an oral, direct factor Xa inhibitor.
Roehrig S, Straub A, Pohlmann J, Lampe T, Pernerstorfer J, Schlemmer KH, Reinemer P, Perzborn E
J Med Chem, (19):5900-5908 2005
MED: 16161994
Discovery of 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (apixaban, BMS-562247), a highly potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation factor Xa.
Pinto DJ, Orwat MJ, Koch S, Rossi KA, Alexander RS, Smallwood A, Wong PC, Rendina AR, Luettgen JM, Knabb RM, He K, Xin B, Wexler RR, Lam PY
J Med Chem, (22):5339-5356 2007
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R. M. Scarborough, J. P. Kanter, K. Sujino, S. S. Zuberi, WO 2008/057972A1, 2008;
Optimization of the beta-aminoester class of factor Xa inhibitors. Part 2: Identification of FXV673 as a potent and selective inhibitor with excellent In vivo anticoagulant activity.
Guertin KR, Gardner CJ, Klein SI, Zulli AL, Czekaj M, Gong Y, Spada AP, Cheney DL, Maignan S, Guilloteau JP, Brown KD, Colussi DJ, Chu V, Heran CL, Morgan SR, Bentley RG, Dunwiddie CT, Leadley RJ, Pauls HW
Bioorg Med Chem Lett, (12):1671-1674 2002
MED: 12039587
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Furugohri
J. Thromb. Haemostasis 2008

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Proteins in UniProt

Coagulation factor X(UniProt - P00742)

Protein structures in PDBe

factor xa - cation inhibitor complex(PDB - 2jkh)
View structure

Search life-sciences literature (45,103,589 articles, preprints and more)

Cation-pi interactions at the active site of factor Xa: dramatic enhancement upon stepwise N-alkylation of ammonium ions.

Affiliations

Authors

ORCIDs linked to this article

Abstract

Full text links

References

Title not supplied

Oral, direct factor Xa inhibitors in development for the prevention and treatment of thromboembolic diseases.

New oral Xa and IIa inhibitors: updates on clinical trial results.

Title not supplied

Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3- [4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene- 2-carboxamide (BAY 59-7939): an oral, direct factor Xa inhibitor.

Discovery of 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (apixaban, BMS-562247), a highly potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation factor Xa.

Title not supplied

R. M. Scarborough, J. P. Kanter, K. Sujino, S. S. Zuberi, WO 2008/057972A1, 2008;

Optimization of the beta-aminoester class of factor Xa inhibitors. Part 2: Identification of FXV673 as a potent and selective inhibitor with excellent In vivo anticoagulant activity.

Title not supplied

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Smart citations by scite.ai
Explore citation contexts and check if this article has been supported or disputed.
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Article citations

Trimethyllysine Reader Proteins Exhibit Widespread Charge-Agnostic Binding via Different Mechanisms to Cationic and Neutral Ligands.

Systematic Study of Heteroarene Stacking Using a Congeneric Set of Molecular Glues for Procaspase-6.

A systematic approach for evaluating the role of surface-exposed loops in trypsin-like serine proteases applied to the 170 loop in coagulation factor VIIa.

Identification of Spiro-Fused Pyrrolo[3,4-a]pyrrolizines and Tryptanthrines as Potential Antitumor Agents: Synthesis and In Vitro Evaluation.

Homology Modeling of the Human P-glycoprotein (ABCB1) and Insights into Ligand Binding through Molecular Docking Studies.

Data

Data that cites the article

Proteins in UniProt

Protein structures in PDBe

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Cation-pi interactions at the active site of factor Xa: dramatic enhancement upon stepwise N-alkylation of ammonium ions.

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R. M. Scarborough, J. P. Kanter, K. Sujino, S. S. Zuberi, WO 2008/057972A1, 2008;

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