8-Cyclopentyl-1,3-dimethylxanthine

Base Information

• Chemical Name: 8-Cyclopentyl-1,3-dimethylxanthine
• CAS No.: 35873-49-5
• Molecular Formula: C12H16 N4 O2
• Molecular Weight: 248.285
• Hs Code.: 29339900
• NSC Number: 101806
• UNII: U7PWT4CPL5
• DSSTox Substance ID: DTXSID70189432
• Nikkaji Number: J48.722H
• Wikipedia: 8-Cyclopentyl-1,3-dimethylxanthine
• Wikidata: Q4644273
• ChEMBL ID: CHEMBL106265
• Mol file: 35873-49-5.mol

Synonyms:8-CPDMX;8-cyclopentyl-1,3-dimethylxanthine;8-cyclopentyltheophylline;PD 116,600;PD 116600;PD-116,600;PD-116600

Chemical Property of 8-Cyclopentyl-1,3-dimethylxanthine

Chemical Property:

• Vapor Pressure: 1.21E-10mmHg at 25°C
• Melting Point: 250-252°C
• Boiling Point: 513.1°Cat760mmHg
• Flash Point: 264.1°C
• PSA: 72.68000
• Density: 1.332g/cm³
• LogP: 0.61790
• Storage Temp.: -20?C Freezer
• Solubility.: H2O: <0.28 mg/mL, slightly soluble
• Water Solubility.: Soluble in 0.1M NaOH. Slightly soluble in water. Also soluble in DMSO at 16mg/ml at 60°C.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 248.12732577
• Heavy Atom Count: 18
• Complexity: 380

Purity/Quality:

98%,99%, ^*data from raw suppliers

8-Cyclopentyl-1,3-dimethylxanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2=C(C(=O)N(C1=O)C)NC(=N2)C3CCCC3
• Uses: A selective A1 adenosine receptor antagonist. Binding activity in rat brain membranes: Ki = 10.9 nM (A1 receptor); Ki = 1440 nM (A2 receptor) A selective A1 adenosine receptor antagonist. Binding activity in rat brain membranes: Ki = 10.9 nM (A1 receptor); Ki = 1440 nM (A2 receptor).

Technology Process of 8-Cyclopentyl-1,3-dimethylxanthine

There total 2 articles about 8-Cyclopentyl-1,3-dimethylxanthine 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:

4,5-Diamino-1,3-dimethyluracil (5440-00-6) + cyclopentanecarboxylic acid (3400-45-1) → 8-cyclopentyltheophylline (35873-49-5)

Guidance literature:

With hydrogenchloride; sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; Yield given. Multistep reaction; 1.) dioxane, H₂O, RT, 4 h, 2.) dioxane, H₂O, reflux, 10 min;

DOI:10.1021/jm00094a022

Reference yield:

→ 8-cyclopentyltheophylline (35873-49-5)

Guidance literature:

5.6-Diamino-1.3-dimethyluracil/Cyclopentancarbonsaeure;

DOI:10.1021/jm00294a016

Reference yield: 14.0%

8-cyclopentyltheophylline (35873-49-5) + 2-(bromomethyl)-1-chloro-3-fluorobenzene (68220-26-8) → 7-(2-chloro-6-fluorobenzyl)-8-cyclopentyl-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

Guidance literature:

With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 60 ℃; for 24h;

upstream raw materials:

4,5-Diamino-1,3-dimethyluracil

cyclopentanecarboxylic acid

Refernces

• 1、 Goodsell et al.. "8-substituted theophyllines. In vitro inhibition of 3',5'-cyclic adenosine monophosphate phosphodiesterase and pharmacological spectrum in mice.". . p. 1202. Retrieved 2007/10/04.