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

doi:10.1021/jm051091j

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 journal › Article › peer-review

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 language	English
Pages (from-to)	3743-3747
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	49
Issue number	12
DOIs	https://doi.org/10.1021/jm051091j
Publication status	Published - 15 Jun 2006

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10.1021/jm051091j

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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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doi = "10.1021/jm051091j",

language = "English",

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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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DO - 10.1021/jm051091j

M3 - Article

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SN - 0022-2623

VL - 49

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JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

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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

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CCDC 282947: Experimental Crystal Structure Determination

CCDC 282948: Experimental Crystal Structure Determination

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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

Abstract

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CCDC 282947: Experimental Crystal Structure Determination

CCDC 282948: Experimental Crystal Structure Determination

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