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N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide

ChemBase编号:73165
分子式:C25H34N4O2
平均质量:422.56306
单一同位素质量:422.26817635
SMILES和InChIs

SMILES:
c1cccc(c1OC)N1CCN(CC1)CCN(c1ncccc1)C(=O)C1CCCCC1
Canonical SMILES:
COc1ccccc1N1CCN(CC1)CCN(C(=O)C1CCCCC1)c1ccccn1
InChI:
InChI=1S/C25H34N4O2/c1-31-23-12-6-5-11-22(23)28-18-15-27(16-19-28)17-20-29(24-13-7-8-14-26-24)25(30)21-9-3-2-4-10-21/h5-8,11-14,21H,2-4,9-10,15-20H2,1H3
InChIKey:
SBPRIAGPYFYCRT-UHFFFAOYSA-N

引用这个纪录

CBID:73165 http://www.chembase.cn/molecule-73165.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide
IUPAC传统名
N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexanecarboxamide
别名
WAY-100635
N-[2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethyl]-N-2-pyridinylcyclohexanecarboxamide Trihydrochloride
WAY 100635 Hydrochloride
CAS号
162760-96-5
146714-97-8
PubChem SID
162038085
PubChem CID
5684

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
PubChem 5684 external link

理论计算性质

理论计算性质

JChem
质子受体 质子供体
LogD (pH = 5.5) 2.904972  LogD (pH = 7.4) 4.079087 
Log P 4.1645226  摩尔折射率 124.4266 cm3
极化性 47.8947 Å3 极化表面积 48.91 Å2
可自由旋转的化学键 里宾斯基五规则 true 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
Methanol expand 查看数据来源
外观
Off-White to Pale Yellow Solid expand 查看数据来源
熔点
176-178°C expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals TRC TRC
Selleck Chemicals -  S2663 external link
Research Area
Description Cancer
Biological Activity
Description WAY 100635 is a potent and selective 5-HT agonist with IC50 of 0.95 nM.
Targets 5-HT
IC50 0.95 nM [1]
In Vitro In dorsal raphe nucleus (DRN) slices superfused with WAY 100635 (10 nM), the majority of putative 5-HT neurons increase their firing rate (13% of baseline rate). In addition, WAY 100635 completely prevents the decrease in firing rate produced by 5-HT (3-15 μM), 8-OH-DPAT (10 nM), 5-carboxamidotryptamine (20 nM) and lesopitron (100 nM). The antagonism exerted by WAY 100635 is fully surmounted by increasing the concentration of 5-HT to 300 μM with an IC50 of 0.95 nM. In hippocampal slices, WAY 100635 (0.5 nM -10 nM) does not alter the resting membrane potential or the membrane input resistance of intracellularly recorded CA1 pyramidal cells. However, WAY 100635 completely prevents not only the hyperpolarization, with an IC50 of 1.3 nM, but also the decrease in membrane input resistance produced by 5-HT and 5-carboxamidotryptamine with IC50 of 22.5 μM and 50 nM, respectively. [1] WAY 100635 has an IC50 of 1.35 nM and is > 100-fold selective for the 5-HT1A site relative to a range of other CNS receptors. The Bmax of [3H]WAY 100635 specific binding is consistently 50-60% greater than that of the agonist radioligand, [3H]8-OH-DPAT. Mn2+, but not guanine nucleotides, inhibits [3H]WAY 100635-specific binding. WAY 100635 has no 5-HT1A receptor agonist actions, but dose-dependently blocks the effects of agonists at both the postsynaptic 5-HT1A receptor in the CA1 region of the hippocampus, and the somatodendritic 5-HT1A receptor locates on dorsal raphe 5-HT neurones. [2] [3H]WAY 100635 has a Kd of approximately 2.5 nM. [3] In the isolated guinea-pig ileum WAY 100635 is a potent and, at high concentrations, an insurmountable antagonist of the 5-HT1A receptor agonist action of 5-carboxamidotryptamine, with an apparent pA2 value (at 0.3 nM) of 9.71. [4] Five minutes after the i.v. injection of [3H]WAY 100635 (4 μCi -7.6 μCi per mouse) the amount of tritium found in the whole brain only accounted for 1.5-1.8% of the injected radioactivity, regional differences in 3H accumulation already correspondes to those of 5-HT1A receptor density. [5] In light of its only recently discovered dopaminergic activity, conclusions drawn from studies that employs WAY 100635 as a selective 5-HT1A antagonist may need to be re-evaluated. [6]
In Vivo [3H]WAY 100635 is shown to bind selectively to brain 5-HT1A receptors, following intravenous administration to mice. WAY 100635 also dose-dependently blocks the ability of 8-OH-DPAT to inhibit the firing of dorsal raphe 5-HT neurones, and to induce the '5-HT syndrome', hypothermia, hyperphagia and to elevate plasma ACTH levels. In the mouse light/dark box anxiety model, WAY 100635 induces anxiolytic-like effects. WAY 100635 has no intrinsic effect on cognition in the delayed-matching-to-position model of short-term memory in the rat, but reverses the disruptive effects of 8-OH-DPAT on motor motivational performance. [2] WAY 100635 blocks the inhibitory action of 8-OH-DPAT on dorsal raphe neuronal firing in the anaesthetised rat at doses which has no inhibitory action per se. In behavioural models, WAY 100635 itself induces no overt behavioural changes but potently antagonises the behavioural syndrome induced by 8-OH-DPAT in the rat and guinea-pig (minimum effective dose = 0.003 mg/kg s.c. and ID50 = 0.01 mg/kg s.c., respectively). WAY 100635 also blocks the hypothermia induced by 8-OH-DPAT in the mouse and rat with ID50 values of 0.01 mg/kg s.c. [4]
Clinical Trials
Features [3H]WAY 100635 is characterised as the first 5-HT1A antagonist radioligand.
Protocol
Cell Assay [1]
Cell Lines Neurons
Concentrations 1 nM -5 nM
Incubation Time 2 minutes -5 minutes
Methods Extracellular recordings are made with glass microelectrodes filled with 2 M NaC1 (12 MΩ-15 MΩ). Cells are identified as 5-HT neurons according to the following criteria: biphasic action potentials of 2 msec to 3 msec in duration, slow (0.5 Hz - 2.0 Hz) and regular pattern of discharge. Firing is evoked in the otherwise silent neurons by adding the alpha-l adrenergic agonist phenylephrine (3 μM) to the superfusing ACSF. Baseline activity is recorded for at least 10 minutes before application of the different drugs. The electric signals are fed into a high-input impedance amplifier, an oscilloscope and an electronic ratemeter triggered by individual action potentials connected to an A/D converter and a personal computer. Using dedicated software, the integrated firing rate is recorded, computed and displayed on a chart recorder as consecutive 10-sec samples. The effects of agonists are evaluated by comparing the mean discharge frequency recorded during the 2 minutes that preceded WAY 100635 application with that recorded at the peak of WAY 100635 action (usually 2-5 minutes after the beginning of application). When the agonists are applied in the presence of the antagonist, the effect of the agonist is compared to baseline firing rate and to the frequency recorded during superfusion of the antagonist alone. The antagonist is left to equilibrate for 10 minutes to 25 minutes before retesting of the action of agonists.
Animal Study [2]
Animal Models Male CD1 mice with 25-30 g body weight
Formulation 0.9% NaC1
Doses 250 μL (30.4 μCi/mL)
Administration Administered via i.v.
References
[1] Corradetti R, et al. J Pharmacol Exp Ther. 1996, 278(2), 679-688.
[2] Fletcher A, et al. Behav Brain Res. 1996, 73(1-2), 337-353.
[3] Hall H, et al. Brain Res. 1997, 745(1-2), 96-108.
[4] Forster EA, et al. Eur J Pharmacol. 1995, 281(1), 81-88.
[5] Laporte AM, et al. Eur J Pharmacol. 1994, 271(2-3), 505-514.
[6] http://en.wikipedia.org/wiki/WAY-100,635
Toronto Research Chemicals -  W498650 external link
WAY 100635 is not only a potent 5-HT1A antagonist, but also has high affinity and efficacy at the dopamine D4 receptor.

参考文献

参考文献

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