S-(+)-Rolipram

Names

[ Name ]:
S-(+)-Rolipram

[Synonym ]:
(4R)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone
S2127_Selleck
(4S)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
1oyn
S- (+)-Rolipram
2-Pyrrolidinone, 4-(3-(cyclopentyloxy)-4-methoxyphenyl)-, (R)-
S-(+)-Rolipram
(4R)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
S-(+)-4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidinone
(S)-4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one
(-)-rolipram
1xn0
(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone
(+)-rolipram
(4S)-4-[3-(Cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one
2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, (4R)-
2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, (4S)-
(S)-(+)-Rolipram

Biological Activity

[Description]:

(S)-(+)-Rolipram is a PDE4-inhibitor and an anti-inflammatory agent, less potent than its R enantiomer.Target: PDE4B; PDE4DRolipram, a selective inhibitor of the cyclic AMP-specific phosphodiesterase (PDE IV). Rolipram did not inhibit 5-lipoxygenase activity but did inhibit human monocyte production of leukotriene B4 (LTB4, IC50 3.5 microM). Rolipram inhibited arachidonic acid-induced inflammation in the mouse, while the low Km-cyclic-GMP PDE inhibitor. Rolipram had a modest effect on LTB4 production in the mouse, but markedly reduced LTB4-induced PMN infiltration [1]. In humans and animals rolipram produces thereby a variety of biological effects. These effects include attenuation of endogenous depression and inflammation in the central nervous system (CNS), both effects are of potential clinical relevance [2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Inflammation/Immunology

[References]

[1]. Griswold, D.E., et al., Effect of selective phosphodiesterase type IV inhibitor, rolipram, on fluid and cellular phases of inflammatory response. Inflammation, 1993. 17(3): p. 333-44.

[2]. Zhu, J., E. Mix, and B. Winblad, The antidepressant and antiinflammatory effects of rolipram in the central nervous system. CNS Drug Rev, 2001. 7(4): p. 387-98.

[3]. MacKenzie SJ, et al. Action of rolipram on specific PDE4 cAMP phosphodiesterase isoforms and on the phosphorylation of cAMP-response-element-binding protein (CREB) and p38 mitogen-activated protein (MAP) kinase in U937 monocyticcells. Biochem J. 2000 Apr

[4]. Korhonen R, et al. Attenuation of TNF production and experimentally induced inflammation by PDE4 inhibitor rolipram is mediated by MAPK phosphatase-1. Br J Pharmacol. 2013 Aug;169(7):1525-36.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
472.7±45.0 °C at 760 mmHg

[ Melting Point ]:
133-136ºC

[ Molecular Formula ]:
C₁₆H₂₁NO₃

[ Molecular Weight ]:
275.343

[ Flash Point ]:
239.7±28.7 °C

[ Exact Mass ]:
275.152130

[ PSA ]:
47.56000

[ LogP ]:
1.43

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.552

[ Storage condition ]:
Store at RT

Safety Information

[ HS Code ]:
2933790090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933790090

[ Summary ]:
2933790090. other lactams. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:9.0%. General tariff:20.0%

Related Compounds

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