85416-73-5 Usage
Description
S-(+)-Rolipram, also known as the S isomer of (±)-Rolipram (R640040), is a potent inhibitor of cyclic AMP-specific phosphodiesterase (PDE4). It is a chiral molecule with distinct biological properties compared to its R enantiomer. S-(+)-Rolipram exhibits anti-inflammatory and anti-depressant activity in the central nervous system, although it is less potent than its R counterpart. Its ability to inhibit PDE4 enzymes plays a crucial role in its therapeutic applications.
Uses
Used in Pharmaceutical Industry:
S-(+)-Rolipram is used as a PDE4 inhibitor for its anti-inflammatory and anti-depressant properties in the central nervous system. Its inhibition of PDE4 enzymes leads to increased levels of cyclic AMP, which in turn modulates various cellular processes and signaling pathways associated with inflammation and depression.
Used in Research Applications:
S-(+)-Rolipram is used as a research tool to study the role of PDE4 enzymes in various biological processes and diseases. Its selectivity for the S isomer allows researchers to investigate the specific effects of PDE4 inhibition in cellular and molecular studies, providing valuable insights into the development of targeted therapies for inflammatory and neuropsychiatric disorders.
Used in Drug Development:
S-(+)-Rolipram serves as a lead compound in the development of new drugs targeting PDE4 enzymes for the treatment of various inflammatory and neuropsychiatric conditions. Its unique properties and selectivity for the S isomer make it an attractive candidate for further optimization and drug design efforts to improve potency, selectivity, and safety profiles.
Biological Activity
Less active enantiomer of the PDE4 inhibitor rolipram (4-(3-(Cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one ).
Check Digit Verification of cas no
The CAS Registry Mumber 85416-73-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,5,4,1 and 6 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 85416-73:
(7*8)+(6*5)+(5*4)+(4*1)+(3*6)+(2*7)+(1*3)=145
145 % 10 = 5
So 85416-73-5 is a valid CAS Registry Number.
85416-73-5Relevant articles and documents
Multistep continuous-flow synthesis of (R)- and (S)-rolipram using heterogeneous catalysts
Tsubogo, Tetsu,Oyamada, Hidekazu,Kobayashi, Shu
, p. 329 - 332 (2015)
Chemical manufacturing is conducted using either batch systems or continuous-flow systems. Flow systems have several advantages over batch systems, particularly in terms of productivity, heat and mixing efficiency, safety, and reproducibility. However, fo
Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis
Ma, Jiguo,Zhou, Qinghai,Song, Guanshui,Song, Yongchang,Zhao, Guoqing,Ding, Kuiling,Zhao, Baoguo
, p. 10588 - 10592 (2021/04/06)
Direct α-functionalization of NH2-free glycinates with relatively weak electrophiles such as α,β-unsaturated esters still remains a big challenge in organic synthesis. With chiral pyridoxal 5 d as a carbonyl catalyst, direct asymmetric conjugated addition at the α-C of glycinate 1 a with α,β-unsaturated esters 2 has been successfully realized, to produce various chiral pyroglutamic acid esters 4 in 14–96 % yields with 81–97 % ee's after in situ lactamization. The trans and cis diastereomers can be obtained at the same time by chromatography and both of them can be easily converted into chiral 4-substituted pyrrolidin-2-ones such as Alzheimer's drug Rolipram (11) with the same absolute configuration via tert-butyl group removal and subsequent Barton decarboxylation.
Efficient synthesis of (?)-(R)- and (+)-(S)-rolipram
Kaur, Ramandeep,Pandey, Satyendra Kumar
, p. 4333 - 4335 (2017/10/17)
A novel, efficient and protecting group free enantioselective synthetic approach of (?)-(R)-1 and (+)-(S)-rolipram 2 is described employing the organocatalyzed asymmetric Michael addition, Henry condensation, Wittig olefination and reductive lactamization
