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The synthesis and in vitro evaluation of a number of N-acyltryptamines are reported. Structural changes include the N-acyl group and the 5- (H,CH3,Halogen), and 2- (Br, Ph) substituents. 5Br (6d) and 2,5-diBr (6j) proved to be high affinity melatonin agonists, thus proving that Br can substitute for the 5-OMe group without loss of affinity to melatonin receptors (mt1, MT2). 6j is the first example of a melatonin agonist devoid of the 5-OMe group and endowed with better affinity for mt1 and MT2 receptors than that of melatonin itself. SAR for selectivity and intrinsic activity of the title compounds were also drawn.
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Reference：
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N912 | ChemSpider