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85416-73-5 分子结构
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(4S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one

ChemBase编号:72843
分子式:C16H21NO3
平均质量:275.34284
单一同位素质量:275.15214354
SMILES和InChIs

SMILES:
c1(c(cc(cc1)[C@H]1CNC(=O)C1)OC1CCCC1)OC
Canonical SMILES:
COc1ccc(cc1OC1CCCC1)[C@H]1CNC(=O)C1
InChI:
InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)/t12-/m1/s1
InChIKey:
HJORMJIFDVBMOB-GFCCVEGCSA-N

引用这个纪录

CBID:72843 http://www.chembase.cn/molecule-72843.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
(4S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
IUPAC传统名
(+)-rolipram
别名
S-(+)-Rolipram
CAS号
85416-73-5
PubChem SID
162037764
PubChem CID
158758

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 价格
Selleck Chemicals
S2127 external link 加入购物车 请登录
数据来源 数据ID
PubChem 158758 external link

理论计算性质

理论计算性质

JChem
Acid pKa 14.28277  质子受体
质子供体 LogD (pH = 5.5) 1.9585267 
LogD (pH = 7.4) 1.9585267  Log P 1.9585268 
摩尔折射率 76.1641 cm3 极化性 29.84816 Å3
极化表面积 47.56 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

安全信息 产品相关信息 生物活性(PubChem)
保存条件
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成盐信息
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详细说明

详细说明

Selleck Chemicals Selleck Chemicals
Selleck Chemicals -  S2127 external link
Research Area
Description Neurological Disease
Biological Activity
Description S-(+)-Rolipram inhibits human monocyte cyclic AMP-specific PDE4 with IC50 of 0.75 μM.
Targets PDE4
IC50 750 nM [1]
In Vitro S-(+)-Rolipram suppresses LPS-induced TNFα expression from human monocyte through inhibiting PDE4 with IC50 about 2 μM. [1] 1 μM S-(+)-Rolipram significantly antagonizes ovalbumin (OA) induced concentration-related contractions of tracheal rings which are isolated from OA-sensitized guinea pigs. [2] S-(+)-Rolipram inhibits PDE4 activity in a CHO-K1 cell line which stably expresses a recombinant full length human PDE-4a with IC50 at 450 nM. [3] Treatment of the human glioma cell line A-172 with Rolipram (including both R- and S-enantiomers of Rolipram) results in increased expression of the cell cycle inhibitors p21 [Cip1] and p27 [Kip1], and decreased activity of cdk2, a cyclindependent kinase essential for cell cycle progression. As a result, the proliferation of A-172 cells is inhibited, with induction of a G1 block. Eventually, Rolipram-treated A-172 cells undergo differentiation, which is followed by apoptotic cell death. [4]
In Vivo In anesthetized, ventilated OA-sensitive guinea pigs, S-(+)-Rolipram reduces OA-induced bronchoconstriction with ID50 values of approximately 0.25 mg/kg i.v. Histamine- and leukotriene D4-induced bronchoconstriction are not affected by doses of S-(+)-Rolipram which abolishes the response to OA. Higher doses (3-10 mg/kg) reduce histamine-, but not the leukotriene D4-induced bronchoconstriction. In conscious OA-sensitive guinea pigs, intragastric pretreatment with S-(+)-Rolipram dose-dependently reduces both the OA-induced decreases in specific conductance as well as the corresponding pulmonary eosinophil influx as assessed by both bronchoalveolar lavage and histological evaluation. [2]
Clinical Trials Rolipram (including both R- and S-enantiomers of Rolipram) is under the Phase I clinical trial for its antidepressant effects on cAMP specific phosphodiesterase (PDE4) in depressed patients.
Features
Protocol
Kinase Assay [1]
PDE Assay PDE activity is determined by the two-step radioisotope method of Thompson et al (1979). The reaction mixture contains: Tris-HCl 20 mM (pH 8.0), MgCl2 10 mM, 2-mercaptoethanol 4 mM, ethyleneglycol-bis-(f-aminoethyl ether) N,N,N',N'-tetraacetic acid (EGTA) 0.2 mM, bovine serum albumin, 0.05 mg/mL. Unless otherwise stated, the substrate concentration is 1 μM. The IC50 values (concentration which produced 50% inhibition of substrate hydrolysis) for the compounds are determined from concentration (0.1 nM to 40 μM)-response curves. At least three concentration-response curves are generated for each agent.
Animal Study [2]
Animal Models Male Hartley guinea pigs
Formulation S-(+)-Rolipram is dissolved in 100% PEG at an appropriate concentration.
Doses 1 mL/kg
Administration Administered via i.v.
References
[1] Souness JE, et al. Br J Pharmacol, 1996, 118(3), 649-658
[2] Underwood DC, et al. J Pharmacol Exp Ther, 1993, 266(1), 306-313
[3] Pon DJ, et al. Cell Biochem Biophys, 1998, 29(1-2), 159-178.
[4] Chen TC, et al. Cancer Biol Ther, 2002, 1(3), 268-276.

参考文献

参考文献

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