Synthesis and pharmacological evaluation of 6a,7-dihydro-6 H,13 H-pyrazino[1,2- a;4,5- a′]diindole analogs as melatonin receptor ligands

Mohamed I. Attia; Justin Julius; Paula A. Witt-Enderby; Darius P. Zlotos

doi:10.1016/j.tet.2006.10.081

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Synthesis and pharmacological evaluation of 6a,7-dihydro-6 H,13 H-pyrazino[1,2- a;4,5- a′]diindole analogs as melatonin receptor ligands

Journal article

Peer reviewed

Synthesis and pharmacological evaluation of 6a,7-dihydro-6 H,13 H-pyrazino[1,2- a;4,5- a′]diindole analogs as melatonin receptor ligands

Mohamed I. Attia, Justin Julius, Paula A. Witt-Enderby and Darius P. Zlotos

Tetrahedron, Vol.63(3), pp.754-760

2007

DOI: https://doi.org/10.1016/j.tet.2006.10.081

Abstract

6a,7-Dihydro-6 H,13 H-pyrazino[1,2- a;4,5- a′]diindole

Dehydrogenation

Melatoninergic ligands

Nitrogen heterocycles

The synthesis of two melatonin-derived analogs of the novel 6a,7-dihydro-6 H,13 H-pyrazino[1,2- a;4,5- a′]diindole ring system is described. The non-methoxy and methoxy analogs, 4a and 4b were prepared in seven steps starting from indoline-2-carboxylic acid 5a and 5-methoxyindoline-2-carboxylic acid 5b, respectively. While 4a exhibited micromolar affinities for both melatonin receptors, the methoxy analog 4b displayed moderate affinity for MT 2 receptors ( K i=0.41 μM) being 4.4-fold higher than for the MT 1 subtype. [Display omitted]

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Title: Synthesis and pharmacological evaluation of 6a,7-dihydro-6 H,13 H-pyrazino[1,2- a;4,5- a′]diindole analogs as melatonin receptor ligands
Creators - without role: Mohamed I. Attia - University of Würzburg
Justin Julius - Duquesne University
Paula A. Witt-Enderby - Duquesne University
Darius P. Zlotos - University of Würzburg
Publication Details: Tetrahedron, Vol.63(3), pp.754-760
Publisher: Elsevier Ltd
Identifiers: 9949450508331
Academic Unit: King Saud University
Language: English
Resource Type: Journal article