SYM 2206
(+/-)-4-(4-AMINOPHENYL)-1,2-DIHYDRO-1-METHYL-2-PROPYLCARBAMOYL-6,7-METHYLENEDIOXYPHTHALAZINE
CAS: 173952-44-8
Molecular Formula: C20H22N4O3
SYM 2206 - Names and Identifiers
SYM 2206 - Physico-chemical Properties
| Molecular Formula | C20H22N4O3 |
| Molar Mass | 366.41 |
| Storage Condition | Store at RT |
SYM 2206 - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.729 ml | 13.646 ml | 27.292 ml |
| 5 mM | 0.546 ml | 2.729 ml | 5.458 ml |
| 10 mM | 0.273 ml | 1.365 ml | 2.729 ml |
| 5 mM | 0.055 ml | 0.273 ml | 0.546 ml |
Last Update：2024-01-02 23:10:35
SYM 2206 - Reference Information
| Application | 8-(4-aminophenyl) -5-methyl-N-propyl-1, 3-dioxocyclopenteno [4,5-G] phthalazine -6(5H)-formamide is an amide organic substance, which can be used as an intermediate in organic synthesis. |
| Preparation | 8-(4-aminophenyl) -5-methyl-N-propyl-1, 3-dioxocyclopenteno [4,5-G] phthalazine -6(5H)-formamide can be made of 4-(4-acetylaminophenyl)-1, 2-dihydro-1-methyl -6, 7-methylhexanedioxyphthalonitrile is used as the reaction raw material, and propyl isocyanate is formed into urea and then acetyl group is hydrolyzed to obtain the step of preparing 4-(4-acetylaminophenyl)-1, 2-dihydro-1-methyl-2-propylcarbamoyl -6, 7-methyldioxo-phthaloyl hydrazine is used to prepare 4-(4-acetylaminophenyl)-1, 2-Dihydro-1-methyl -6, 7-methylhexanedioxyphthalonitrile (0.10g,0.31mmol) was dissolved in dichloromethane (5mL) and treated with propyl isocyanate (0.5mL) under stirring. After 5 hours, add propyl isocyanate (0.5mL) and stir the mixture for 48 hours. The solvent was blown dry with a nitrogen stream, and the residue was chromatographed on silica gel, eluted with a gradient of 33% hexane/EtOAc to 25% hexane/EtOAc. The obtained product is a light yellow foam solid (108mg,86%). 200 MHz 1H NMR (CDCl3); δ 7.63 (ABq, 4H, J = 9.4 Hz, ArH'), 7.40 (bs, 1H, ArNH), 6.77 (s, 1H, ArH), 6.74 (s, 1H, ArH), 6.62 (t, 1H, J = 8.5 Hz, NHCH2), 6.02 (s, 2H, OCH2O), 5.71 (q, 1H, J = 10.9 Hz, CHCH3), 3.33 (dt, 1H, J = 8.5 Hz, J = 7.8 Hz, NHCHCH2), 2.18 (s, 3H, COCH3), 1.61 ( q, 2H, J =7.8 Hz, CH2CH2CH3), 1.27 (d, 3H, J = 10.9 Hz, CHCH3), 0.98 (t, 3H, J = 7.8 Hz, CH2CH3). Step 2. Preparation of 8-(4-aminophenyl) -5-methyl-N-propyl-1, 3-dioxocyclopenteno [4,5-G] phthalazine -6(5H)-formamide 4-(4-acetylaminophenyl)-1, 2-dihydro-1-methyl-2-propylcarbamoyl -6, 7-methyldioxo-phthaloyl hydrazide (0.10g,0.25mmol) was dissolved in methanol (8mL) solution containing 1N sodium hydroxide (4mL) and heated and refluxed for 72 hours. The solution was cooled to ambient temperature, diluted with EtOAc(30mL), and washed with water (30mL). The water layer was extracted with EtOAc(25mL), and the combined organic layer was dried (MgSO4) and evaporated in vacuum. The crude product was chromatographed on silica gel and eluted with 50% hexane/EtOAc to obtain the pure product, which was a light yellow foam solid (75mg,82%). 200 MHz 1H NMR (CDCl3); δ 7.41 (d, 2H, J = 6.5 Hz, ArH), 6.81 (s, 1H, ArH), 6.77 (d, 2H, J = 6.5 Hz, ArH), 6.71 (s, 1H, ArH), 6.00 (s, 2H, OCH2O), 5.67 (q, 1H, J = 6.7 Hz, CHCH3), 3.85 (brs, 2H, NH2), 3.30 (dt, 2H, J = 8.3 Hz, J = 6.2 Hz, NHCH2CH2) , 1.58 (m, 2H, CH2CH2CH3), 1.24 (d, 3H, J = 6.7 Hz, CHCH3), 0.95 (t, 3H, J = 7.5 Hz, CH2CH3). |
| biological activity | SYM2206 is an effective, non-competitive AMPA receptor antagonist with an IC50 value of 1.6 μM. SYM2206 can block the continuous current mediated by Nav1.6. |
Last Update：2024-04-09 15:16:38
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