Rational approaches towards reversible inhibition of type B monoamine oxidase. Design and evaluation of a novel 5H-Indeno[1,2-c]pyridazin-5-one derivative.

Ooms, Frédéric; Frédérick, Raphaël; Durant, François; Petzer, Jacobus P; Castagnoli, Neal; Van der Schyf, Cornelis J; Wouters, Johan

doi:10.1016/s0960-894x(02)00838-7

Article (Scientific journals)

Rational approaches towards reversible inhibition of type B monoamine oxidase. Design and evaluation of a novel 5H-Indeno[1,2-c]pyridazin-5-one derivative.

Ooms, Frédéric; Frédérick, Raphaël; Durant, François et al.

2003 • In Bioorganic and Medicinal Chemistry Letters, 13 (1), p. 69 - 73

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/320301

DOI
10.1016/s0960-894x(02)00838-7

PubMed
12467619

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Keywords :

Monoamine Oxidase Inhibitors; Pyridazines; Monoamine Oxidase; Drug Design; Humans; Hydrogen Bonding; Hydrophobic and Hydrophilic Interactions; Inhibitory Concentration 50; Kinetics; Models, Molecular; Monoamine Oxidase/chemistry; Monoamine Oxidase/metabolism; Monoamine Oxidase Inhibitors/chemical synthesis; Monoamine Oxidase Inhibitors/pharmacology; Pyridazines/chemical synthesis; Pyridazines/pharmacology; Structure-Activity Relationship; Biochemistry; Molecular Medicine; Molecular Biology; Pharmaceutical Science; Drug Discovery; Clinical Biochemistry; Organic Chemistry

Abstract :

[en] The stereoelectronic properties of several potent reversible monoamine oxidase B (MAO-B) inhibitors were studied with a view to develop a pharmacophore model for reversible MAO-B inhibition. This study suggested that important specific H-bond and hydrophobic interactions are required for potent and selective MAO-B inhibition. These requirements were applied in the design and synthesis of a novel reversible and selective MAO-B inhibitor, 3-methyl-8-(4,4,4-trifluoro-butoxy)indeno[1,2-c]pyridazin-5-one, that is ca. 7000 times more selective as an inhibitor for MAO-B than for MAO-A, with K(i(MAO-B)) in the low nanomolar range.

Disciplines :

Chemistry

Author, co-author :

Ooms, Frédéric ; Université de Liège - ULiège > HEC Liège Research > HEC Liège Research: Strategy & Performance for the Society ; Facultés Universitaires Notre-Dame de la Paix, Laboratoire de Chimie Moléculaire Structurale, B-5000 Namur, Belgium

Frédérick, Raphaël; Facultes Univ. Notre-Dame de la Paix, Lab. de Chimie Molec. Structurale, B-5000 Namur, Belgium

Durant, François; Facultes Univ. Notre-Dame de la Paix, Lab. de Chimie Molec. Structurale, B-5000 Namur, Belgium

Petzer, Jacobus P; Department of Chemistry, Harvey W. Peters Center, VA-MD Regional Col. of Vet. Medicine, Blacksburg, VA 24061-0212, United States

Castagnoli, Neal

Van der Schyf, Cornelis J; Department of Chemistry, Harvey W. Peters Center, VA-MD Regional Col. of Vet. Medicine, Blacksburg, VA 24061-0212, United States ; Department of Biomedical Sciences, VA-MD Regional Col. of Vet. Medicine, Virginia Tech., Blacksburg, VA 24061-0212, United States ; Dept. of Pharmaceutical Sciences, Texas Tech. Univ. Health Sci. Ctr., School of Pharmacy, Amarillo TX 79106, United States

Wouters, Johan; Facultes Univ. Notre-Dame de la Paix, Lab. de Chimie Molec. Structurale, B-5000 Namur, Belgium

Language :

English

Title :

Rational approaches towards reversible inhibition of type B monoamine oxidase. Design and evaluation of a novel 5H-Indeno[1,2-c]pyridazin-5-one derivative.

Publication date :

06 January 2003

Journal title :

Bioorganic and Medicinal Chemistry Letters

ISSN :

0960-894X

eISSN :

1464-3405

Publisher :

Elsevier BV, England

Volume :

Issue :

Pages :

69 - 73

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://api.elsevier.com/content/article/PII:S0960894X02008387?httpAccept=text/xml

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Bibliography

Weyler W., Hsu Y.P., Breakefield X.O. Pharmacol. Ther. 47:1990;391.
Grimsby J., Lan N.C., Neve R., Chen K., Shih J.C. J. Neurochem. 55:1990;1166.
Wouters J. Curr. Med. Chem. 5:1998;137.
Lebreton L., Curet O., Gueddari S., Mazouz F., Bernard S., Burstein C., Milcent R. J. Med. Chem. 38:1995;4786.
Mazouz F., Gueddari S., Burstein C., Mansuy D., Milcent R. J. Med. Chem. 36:1993;1157.
Mazouz F., Lebreton L., Milcent R., Burstein C. Eur. J. Med. Chem. 25:1990;659.
Mazouz F., Lebreton L., Milcent R., Burstein C. Eur. J. Med. Chem. 23:1988;441.
Kneubühler S., Thull U., Altomare C., Carta V., Gaillard P., Carrupt P.A., Carotti A., Testa B. J. Med. Chem. 38:1995;3874.
Kneubühler S., Carta V., Altomare C., Carotti A., Testa B. Helv. Chim. Acta. 76:1993;1954.
Arvanitis A.G., Scholfield E.L., Grigoriadis D., Heytler P.G., Bowdle J., Chorvat R.J. Bioorg. Med. Chem. Lett. 6:1996;115.
Wouters J., Ooms F., Jegham S., Koenig J.J., George P., Durant F. Eur. J. Med. Chem. 32:1997;721.
Binda C., Newton-Vinson P., Hubalek F., Edmondson D.E., Mattevi A. Nat. Struct. Biol. 9:2002;22.
Rey S., Caron G., Ermondi G., Gaillard P., Pagliara A., Carrupt P.A., Testa B. J. Mol. Graphics Model. 19:2001;521.
Gaillard P., Carrupt P.A., Testa B., Boudon A. J. Comput. Aided Mol. Des. 8:1994;83.
Ooms, F. Rational Approach of the Reversible Inhibition of Type A and B MAO. Design and Synthesis of Original 5H-indeno[1,2-c]pyridazin-5-one Derivatives. PhD Thesis, FUNDP, Namur, 2000.
Salach J.I., Weyler W. Methods Enzymol. 142:1987;627.
Inoue H., Castagnoli K., Van der Schyf C.J., Mabic S., Igarashi K., Castagnoli N. Jr. J. Pharmacol. Exp. Ther. 291:1999;856.
Bradford M.M. Anal. Biochem. 72:1976;247.
Bissel, P.; Bigley, M. C.; Castagnoli, K.; Castagnoli, N., Jr. Bioorg. Med. Chem. 2002, 10, 3031.
Segel I.H. Enzyme Kinetics. 1993;Wiley, New York. p 100.
Jones G., Willett P., Glen R.C., Leach A.R., Taylor R. J. Mol. Biol. 267:1997;727.