916487-15-5

Upstream product

• 34713-98-9 (R)-(-)-α-methoxyphenylacetyl chloride 
• 916487-06-4 7-nitro-6H-[1,3]methylenedioxy[4,5-g]chromene 
• 533-31-3 Sesamol 
• 4720-68-7 4,5-methylenedioxy-2-hydroxybenzaldehyde 
• 3966-32-3 (R)-methoxyphenylacetic acid 

Relevant academic research and scientific papers

TRANS-FUSED CHROMENOISOQUINOLINES SYNTHESIS AND METHODS FOR USE

Optionally substituted chromenoisoquinolines and analogs and derivatives thereof are described herein. In addition, syntheses of these compounds are described herein. In addition, uses of these compounds as dopamine receptor binding compounds are described herein.

trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: Synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist

We report the synthesis of trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H- chromeno[3,4-c]isoquinoline hydrochloride 6 and the resolution of its enantiomers. This new compound is an oxygen bioisostere of the potent dopamine D1-selective full agonist dihydrexidine. The initial synthetic approach involved, as a key step, a Suzuki coupling between a chromene triflate and a boronate ester, followed by isoquinoline formation and reduction of the resulting isoquinoline. Subsequently, a more efficient route was developed that involved conjugate addition of an aryl Grignard reagent to a 2-nitrochromene. The title compound possessed high affinity (Ki = 20-30 nM) for porcine D1-like receptors in native striatal tissue and full intrinsic activity at cloned human dopamine D1 receptors but had much lower affinity at dopamine D2-like receptors (Ki = 3000 nM). The binding and functional properties of this compound illustrate again the utility of constructing dopamine D1 agonist ligands around the β-phenyldopamine pharmacophore template.