Biomaterial Database

Kynurenamines as neural nitric oxide synthase inhibitors. 2005

Antonio Entrena, and M Encarnación Camacho, and M Dora Carrión, and Luisa C López-Cara, and Guillermo Velasco, and Josefa León, and Germaine Escames, and Darío Acuña-Castroviejo, and Víctor Tapias, and Miguel A Gallo, and Antonio Vivó, and Antonio Espinosa

Departamento de Química Farmacéutica y Orgánica, Facultad de Farmacia, Universidad de Granada, 18071 Granada, Spain.

To find new compounds with potential neuroprotective activity, we have designed, synthesized, and characterized a series of neural nitric oxide synthase (nNOS) inhibitors with a kynurenamine structure. Among them, N-[3-(2-amino-5-methoxyphenyl)-3-oxopropyl]acetamide is the main melatonin metabolite in the brain and shows the highest activity in the series, with an inhibition percentage of 65% at a 1 mM concentration. The structure-activity relationship of the new series partially reflects that of the previously reported 2-acylamido-4-(2-amino-5-methoxyphenyl)-4-oxobutyric acids, endowed with a kynurenine-like structure. Structural comparisons between these new kinurenamine derivatives, kynurenines, and 1-acyl-3-(2-amino-5-methoxyphenyl)-4,5-dihydro-1H-pyrazole derivatives also reported confirm our previous model for the nNOS inhibition.

UI	MeSH Term	Description	Entries
D007735	Kynuramine	An aromatic ketone containing the aniline structure (ANILINE COMPOUNDS).	Diaminopropiophenone,2,3-Diaminopropiophenone,2,3 Diaminopropiophenone
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D003342	Corpus Striatum	Striped GRAY MATTER and WHITE MATTER consisting of the NEOSTRIATUM and paleostriatum (GLOBUS PALLIDUS). It is located in front of and lateral to the THALAMUS in each cerebral hemisphere. The gray substance is made up of the CAUDATE NUCLEUS and the lentiform nucleus (the latter consisting of the GLOBUS PALLIDUS and PUTAMEN). The WHITE MATTER is the INTERNAL CAPSULE.	Lenticular Nucleus,Lentiform Nucleus,Lentiform Nuclei,Nucleus Lentiformis,Lentiformis, Nucleus,Nuclei, Lentiform,Nucleus, Lenticular,Nucleus, Lentiform,Striatum, Corpus
D004791	Enzyme Inhibitors	Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D050601	Kynurenine 3-Monooxygenase	An NADPH-dependent flavin monooxygenase that plays a key role in the catabolism of TRYPTOPHAN by catalyzing the HYDROXYLATION of KYNURENINE to 3-hydroxykynurenine. It was formerly characterized as EC 1.14.1.2 and EC 1.99.1.5.	Kynurenine 3-Hydroxylase,Kynurenine Hydroxylase,L-Kynurenine-3-Hydroxylase,3-Hydroxylase, Kynurenine,3-Monooxygenase, Kynurenine,Hydroxylase, Kynurenine,Kynurenine 3 Hydroxylase,Kynurenine 3 Monooxygenase,L Kynurenine 3 Hydroxylase
D051381	Rats	The common name for the genus Rattus.	Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus
D052248	Nitric Oxide Synthase Type I	A CALCIUM-dependent, constitutively-expressed form of nitric oxide synthase found primarily in NERVE TISSUE.	NCNOS Enzyme,NOS1 Protein,Neural Constitutive Nitric Oxide Synthase,Neuronal Nitric Oxide Synthase,Nitric Oxide Synthase, Type I,nNOS Enzyme