(+/-)-4-(4-Aminophenyl)-1,2-dihydro-1-methyl-2-propylcarbamoyl-6,7-methylenedioxyphthalazine

SYM 2206 is a potent, selective and noncompetitive AMPA receptor inhibitor.

ChEBI: 8-(4-aminophenyl)-5-methyl-N-propyl-5H-[1,3]dioxolo[4,5-g]phthalazine-6-carboxamide is a member of phthalazines.

Novel, potent, non-competitive AMPA receptor antagonist (IC 50 = 2.8 μ M ). Acts allosterically at the same regulatory site as GYKI 52466 and 53655 and other benzodiazepines but does not bind to the central diazepine binding site. Selective for AMPA relative to kainate receptor sub-types. Similar potency to GYKI 53655. Anticonvulsant in vivo .

The compound can be produced through the route below[1],
(a) TMEDA,n-BuLi, THF; (b) H2NNH2 2HCI, MeOH, H2O; (c) Ac2O, CHCI3; (d) MeLi, THF;(e) RNCO, CH2CI2; (f) 2N NaOH, MeOH, reflux.

[1] ALLOSTERIC MODULATORS OF THE AMPA RECEPTOR: NOVEL 6-SUBSTITUTED DIHYDROPHTHALAZINES. Bioorganic & Medicinal Chemistry Letters 9 (1999) 539-542. DOI:10.1016/S0960-894X(99)00044-X