Rolipram

Base Information

• Chemical Name: Rolipram
• CAS No.: 61413-54-5
• Molecular Formula: C16H21NO3
• Molecular Weight: 275.348
• Hs Code.: 29337900
• European Community (EC) Number: 262-771-1
• NSC Number: 760125
• UNII: K676NL63N7
• DSSTox Substance ID: DTXSID3044124
• Nikkaji Number: J18.478K
• Wikipedia: Rolipram
• Wikidata: Q410285
• NCI Thesaurus Code: C72842
• Pharos Ligand ID: JYQ6T3D5MV52
• Metabolomics Workbench ID: 146569
• ChEMBL ID: CHEMBL63
• Mol file: 61413-54-5.mol

Synonyms:Rolipram;ZK 62711;ZK-62711;ZK62711

Chemical Property of Rolipram

Chemical Property:

• Appearance/Colour: yellowish solid
• Vapor Pressure: 4.17E-09mmHg at 25°C
• Melting Point: 127-133 °C
• Refractive Index: 1.552
• Boiling Point: 472.7 °C at 760 mmHg
• PKA: 16.02±0.40(Predicted)
• Flash Point: 239.7 °C
• PSA: 47.56000
• Density: 1.155 g/cm³
• LogP: 2.94890
• Storage Temp.: 0-6°C
• Solubility.: H2O: 0.2 mg/mL
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 275.15214353
• Heavy Atom Count: 20
• Complexity: 341

Purity/Quality:

99.9% ^*data from raw suppliers

Rolipram ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-11
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3
• Recent ClinicalTrials: Antidepressant Effects on cAMP Specific Phosphodiesterase (PDE4) in Depressed Patients
• Description: Rolipram (61413-54-5) is a selective inhibitor of cAMP-specific phosphodiesterase (PDE4), IC50 = 1 μM. Displays beneficial effects in neurodegenerative diseases. Rolipram also displays anti-inflammatory activity and synergizes with forskolin (cat.# 10-2073). Cell permeable.
• Uses: antipsychotic A selective, cell permeable inhibitor of cAMP-specific phosphodiesterase (PDE4). Pharmacological tool for characterization of phosphodiesterase isoenzymes. (±)-Rolipram is a cAMP-specific phosphodiesterase 4 (PDE4) inhibitor.

Technology Process of Rolipram

There total 52 articles about Rolipram which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tert-Butyl (+/-)-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one-1-carboxylate (360042-78-0) → Rolipram (61413-54-5)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1021/jo0484880

Reference yield: 96.0%

C9H9N3O3S → Rolipram (61413-54-5)

Guidance literature:

C₉H₉N₃O₃S; In chloroform; at 60 ℃; for 3h; Inert atmosphere;

With dmap; In chloroform; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.202003280

Reference yield: 95.0%

(+/-)-1-Benzyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one (146426-63-3) → Rolipram (61413-54-5)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; at -40 ℃; for 0.166667h;

DOI:10.1002/1521-3765(20010817)7:16<3533::AID-CHEM3533>3.0.CO;2-E

upstream raw materials:

N-(tert-butoxycarbonyl)pyrrol-2(5H)-one

4-bromo-2-cyclopentyloxyanisole

(+/-)-1-Benzyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one

tert-Butyl (+/-)-4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one-1-carboxylate

Downstream raw materials:

R/S-desmethylrolipram

4-(3-cyclopentyloxy-4-methoxyphenyl)-1-(3-nitrophenyl)-pyrrolidin-2-one

Refernces

• 1、 Connon, Stephen J.,Craig, Ryan,Smith, Simon N.. "Divergent Synthesis of γ-Amino Acid and γ-Lactam Derivatives from meso-Glutaric Anhydrides". supporting information. p. 13378 - 13382. Retrieved 2020/10/02.
• 2、 Tomar, Radha,Bhattacharya, Debabrata,Babu, Srinivasarao Arulananda. "Assembling of medium/long chain-based β-arylated unnatural amino acid derivatives via the Pd(II)-catalyzed sp3 β-C-H arylation and a short route for rolipram-type derivatives". . p. 2447 - 2465. Retrieved 2019/03/26.