(+/-)-4-(4-AMINOPHENYL)-1,2-DIHYDRO-1-METHYL-2-PROPYLCARBAMOYL-6,7-METHYLENEDIOXYPHTHALAZINE Chemical Properties

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

Store at RT

solubility 

DMSO : 100 mg/mL (272.92 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)

form 

Powder

pka

15.26±0.60(Predicted)

color 

Light yellow to yellow

CAS DataBase Reference

173952-44-8

(+/-)-4-(4-AMINOPHENYL)-1,2-DIHYDRO-1-METHYL-2-PROPYLCARBAMOYL-6,7-METHYLENEDIOXYPHTHALAZINE Usage And Synthesis

Uses

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

Definition

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

Biological Activity

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 .

Synthesis

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.

References

[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

(+/-)-4-(4-AMINOPHENYL)-1,2-DIHYDRO-1-METHYL-2-PROPYLCARBAMOYL-6,7-METHYLENEDIOXYPHTHALAZINE(173952-44-8)Related Product Information

• 4-Aminodiphenylamine
• N-Methylbenzamide
• (+/-)-4-(4-AMINOPHENYL)-1,2-DIHYDRO-1-METHYL-2-PROPYLCARBAMOYL-6,7-METHYLENEDIOXYPHTHALAZINE
• BENZO[1,3]DIOXOL-5-YLMETHYL-HYDRAZINE