| Identification | Back Directory | [Name]
4-Hydroxy-N-[4-methoxy-7-(4-morpholinyl)-2-benzothiazolyl]-4-methyl-1-piperidinecarboxamide | [CAS]
870070-55-6 | [Synonyms]
CS-297
SYN-115
Tozadenant
Tozadenant (SYN-115)
SYN-115 (Tozadenant)
SYN-115;SYN115;SYN 115
4-Hydroxy-N-[4-methoxy-7-...
4-Methoxy-7-morpholino-2-[(4-hydroxy-4-methylpiperidino)carbonylamino]benzothiazole
4-hydroxy-N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)-4-methylpiperidine-1-carboxamide
4-Hydroxy-N-[4-methoxy-7-(4-morpholinyl)-2-benzothiazolyl]-4-methyl-1-piperidinecarboxamide
1-Piperidinecarboxamide, 4-hydroxy-N-[4-methoxy-7-(4-morpholinyl)-2-benzothiazolyl]-4-methyl- | [Molecular Formula]
C19H26N4O4S | [MDL Number]
MFCD21642026 | [MOL File]
870070-55-6.mol | [Molecular Weight]
406.5 |
| Chemical Properties | Back Directory | [density ]
1.374 | [storage temp. ]
Store at -20°C | [solubility ]
insoluble in EtOH; insoluble in H2O; ≥20.35 mg/mL in DMSO | [form ]
Powder | [pka]
14.95±0.20(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C19H26N4O4S/c1-19(25)5-7-23(8-6-19)18(24)21-17-20-15-14(26-2)4-3-13(16(15)28-17)22-9-11-27-12-10-22/h3-4,25H,5-12H2,1-2H3,(H,20,21,24) | [InChIKey]
XNBRWUQWSKXMPW-UHFFFAOYSA-N | [SMILES]
N1(C(NC2=NC3=C(OC)C=CC(N4CCOCC4)=C3S2)=O)CCC(O)(C)CC1 |
| Hazard Information | Back Directory | [Description]
Tozadenant is an adenosine A2A receptor antagonist (Kis = 11.5 and 6 nM for the human and rhesus monkey receptors, respectively). It increases the distance traveled and reduces contralateral asymmetry in the open field test in a rat model of Parkinson''s disease induced by 6-OHDA when administered at a dose of 30 mg/kg. Tozadenant (150 mg/kg) reverses locomotor deficits and restores novel object-stimulated locomotion in a marmoset model of MPTP-induced Parkinson''s disease. | [Uses]
Tozadenant is an adenosine A2A receptor antagonist, with Ki of 11.5 nM on human A2A and 6 nM on rhesus A2A. | [Definition]
ChEBI: Tozadenant is a member of benzothiazoles. | [Synthesis]
Phenyl (4-methoxy-7-morpholin-4-ylbenzo[D]thiazol-2-yl) carbamate (3.2 g, 8.3 mmol) and 4-methyl-4-hydroxypiperidine were used as raw materials and both were dissolved in trichloromethane (50 ml) in the presence of N-ethyl diisopropylamine (4.4 ml, 25 mmol). Subsequently, a mixed solution of trichloromethane (3 ml) and tetrahydrofuran (3 ml) of 4-hydroxy-4-methylpiperidine was added to this solution. The reaction mixture was heated to reflux for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and washed sequentially with saturated aqueous sodium carbonate solution (15 ml) and water (2 x 5 ml). The organic phase was dried over magnesium sulfate and the solvent was concentrated under reduced pressure, the resulting crude product was recrystallized from ethanol to afford the target compound 4-hydroxy-N-[4-methoxy-7-(4-morpholinyl)-2-benzothiazolyl]-4-methyl-1-piperidinecarboxamide as white crystals in 78% yield, melting point 236 °C. Mass spectral analysis showed m/e = 407 (M + H+). | [in vivo]
18F-MNI-444 regional uptake is consistent with A2A receptor distribution in the brain. Selectivity is demonstrated by dose-dependent blocking by tozadenant (1.5, 10.5 mg/kg) and preladenant[1]. | [target]
adenosine A2A receptor | [References]
hauser ra, olanow cw, kieburtz kd et al. tozadenant (syn115) in patients with parkinson's disease who have motor fluctuations on levodopa: a phase 2b, double-blind, randomised trial. lancet neurol. 2014 aug;13(8):767-76. |
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| Company Name: |
Elucigen bio Gold
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| Tel: |
13501719342; 13501719342 |
| Website: |
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| Company Name: |
Tetranov Biopharm
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| Tel: |
13526569071 |
| Website: |
http://www.leadmedpharm.com/index.html |
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