Synthesis, structural reassignment, and biological activity of type B MAO inhibitors based on the 5H-indeno[1,2-c]pyridazin-5-one core

R. Frédérick, W. Dumont, F. Ooms, L. Aschenbach, C.J. Van Der Schyf, N. Castagnoli, J. Wouters, A. Krief

Research output: Contribution to journalArticle

Abstract

The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[1,2-c]pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C(8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[1,2-c]pyridazin-5-one core at C(7) vs C(8) dramatically influences the MAO-inhibiting properties of these compounds.
Original languageEnglish
Pages (from-to)3743-3747
Number of pages5
JournalJournal of Medicinal Chemistry
Volume49
Issue number12
DOIs
Publication statusPublished - 15 Jun 2006

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Monoamine Oxidase Inhibitors
Monoamine Oxidase
Enzyme Inhibitors
pyridazine

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title = "Synthesis, structural reassignment, and biological activity of type B MAO inhibitors based on the 5H-indeno[1,2-c]pyridazin-5-one core",
abstract = "The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[1,2-c]pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C(8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[1,2-c]pyridazin-5-one core at C(7) vs C(8) dramatically influences the MAO-inhibiting properties of these compounds.",
author = "R. Fr{\'e}d{\'e}rick and W. Dumont and F. Ooms and L. Aschenbach and {Van Der Schyf}, C.J. and N. Castagnoli and J. Wouters and A. Krief",
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language = "English",
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journal = "J. Med. Chem.",
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Synthesis, structural reassignment, and biological activity of type B MAO inhibitors based on the 5H-indeno[1,2-c]pyridazin-5-one core. / Frédérick, R.; Dumont, W.; Ooms, F.; Aschenbach, L.; Van Der Schyf, C.J.; Castagnoli, N.; Wouters, J.; Krief, A.

In: Journal of Medicinal Chemistry, Vol. 49, No. 12, 15.06.2006, p. 3743-3747.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis, structural reassignment, and biological activity of type B MAO inhibitors based on the 5H-indeno[1,2-c]pyridazin-5-one core

AU - Frédérick, R.

AU - Dumont, W.

AU - Ooms, F.

AU - Aschenbach, L.

AU - Van Der Schyf, C.J.

AU - Castagnoli, N.

AU - Wouters, J.

AU - Krief, A.

PY - 2006/6/15

Y1 - 2006/6/15

N2 - The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[1,2-c]pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C(8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[1,2-c]pyridazin-5-one core at C(7) vs C(8) dramatically influences the MAO-inhibiting properties of these compounds.

AB - The synthesis and enzyme inhibitor properties of reversible type B monoamine oxidase inhibitors are described. These compounds belong to the 5H-indeno[1,2-c]pyridazine family and possess a hydrophobic benzyloxy or 4,4,4-trifluorobutoxy side chain which, in contrast to a previous assignment, has been unambiguously located at C(8) of the heterocyclic moiety. Investigation of the regioisomeric structures establishes that substitution of the 5H-indeno[1,2-c]pyridazin-5-one core at C(7) vs C(8) dramatically influences the MAO-inhibiting properties of these compounds.

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U2 - 10.1021/jm051091j

DO - 10.1021/jm051091j

M3 - Article

VL - 49

SP - 3743

EP - 3747

JO - J. Med. Chem.

JF - J. Med. Chem.

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