| Identification | Back Directory | [Name]
1-[3-(4-Bromo-1-methyl-1H-pyrazol-5-yl)-4-methoxyphenyl]-3-(2,4-difluorophenyl)urea | [CAS]
839713-36-9 | [Synonyms]
APD125
APD-125
APD 125
Nelotanserin
APD125(Nelotanserin)
APD125;APD-125;APD 125
APD125; APD-125; APD 125; NELOTANSERIN
1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(2,4-difluorophenyl)urea
1-[3-(4-Bromo-1-methyl-1H-pyrazol-5-yl)-4-methoxyphenyl]-3-(2,4-difluorophenyl)urea
1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxyphenyl]-3-(2,4-difluorophenyl)urea
Urea, N-[3-(4-broMo-1-Methyl-1H-pyrazol-5-yl)-4-Methoxyphenyl]-N'-(2,4-difluorophenyl)- | [Molecular Formula]
C18H15BrF2N4O2 | [MDL Number]
MFCD16619341 | [MOL File]
839713-36-9.mol | [Molecular Weight]
437.24 |
| Chemical Properties | Back Directory | [Boiling point ]
425.9±45.0 °C(Predicted) | [density ]
1.55±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:32.0(Max Conc. mg/mL);73.2(Max Conc. mM) | [form ]
Solid | [pka]
12.29±0.70(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
Nelotanserin is a potent selective 5-HT2A inverse agonist, nelotanserin has low nanomolar potency on the 5-HT2A receptor with at least 30- and 5000-fold selectivity compared with 5-HT2C and 5-HT2B receptors. | [Definition]
ChEBI: Nelotanserin is a member of pyrazoles and a ring assembly. | [Synthesis]
3-(4-bromo-1-methyl-1H-pyrazol-5-yl)-4-methoxyaniline (16.7 kg) was dissolved in acetonitrile (78.6 kg) in a 200 liter glass jacketed reactor under nitrogen protection. Top stirring was turned on and the internal temperature was controlled within the specified range. Subsequently, 2,4-difluorophenyl isocyanate was slowly added to keep the temperature of the reaction system stable. Upon completion of the reaction, the target product 1-(3-(4-bromo-1-methyl-1H-pyrazol-5-yl)-4-methoxyphenyl)-3-(2,4-difluorophenyl)urea was isolated and purified by appropriate post-treatment steps. | [in vivo]
Each compound is tested in a minimum of five rats by oral gavage with administration occurring in the middle of the inactive period, 6 h after light onset. The delta power during non-REM sleep (NREMS) is significantly different between all the analogues tested and the vehicle control. Nelotanserin (Compound 39) produces significant increases in delta power that persist for the first 4 h following dosing. Significant differences are found, however, in NREMS bout length. Nelotanserin significantly increases NREMS bout length during the first hour following dosing, and 3 does so during the second hour. In conjunction with this increased NREM bout duration, the number of NREM bouts decrease during the first hour for Nelotanserin (p<0.01) as well as for compound 15 (p<0.05)[2]. | [IC 50]
5-HT2A Receptor: 1.7 nM (IC50); 5-HT2C Receptor: 79 nM (IC50); 5-HT2B Receptor: 791 nM (IC50) | [storage]
Store at -20°C | [References]
[1] Patent: US2016/67216, 2016, A1. Location in patent: Paragraph 0834; 0835
[2] Patent: WO2010/62321, 2010, A1. Location in patent: Page/Page column 75-76
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1923 - 1936
[4] Patent: WO2006/81335, 2006, A2. Location in patent: Page/Page column 34-37 |
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