8-Cyclopentyl-1,3-dipropylxanthine

Base Information

• Chemical Name: 8-Cyclopentyl-1,3-dipropylxanthine
• CAS No.: 102146-07-6
• Molecular Formula: C₁₆H₂₄N₄O₂
• Molecular Weight: 304.392
• Hs Code.: 2933990090
• European Community (EC) Number: 634-445-2
• UNII: 9PTP4FOI9E
• DSSTox Substance ID: DTXSID50144706
• Nikkaji Number: J126.311K
• Wikipedia: Dipropylcyclopentylxanthine
• Wikidata: Q5280076
• Pharos Ligand ID: 7BUV1K5GWY5M
• Metabolomics Workbench ID: 66339
• ChEMBL ID: CHEMBL183
• Mol file: 102146-07-6.mol

Synonyms:1,3-dipropyl-8-cyclopentylxanthine;1,3-DPCPX;8-cyclopentyl-1,3-dipropylxanthine;8-cyclopentyl-3,7-dihydro-1,3-dipropyl-1H-purin-2,6-dione;DPCPX;PD 116948;PD-116,948

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

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.59E-11mmHg at 25°C
• Melting Point: 178°C
• Boiling Point: 535.1°Cat760mmHg
• PKA: 9.01±0.70(Predicted)
• Flash Point: 277.4°C
• PSA: 72.68000
• Density: 1.195g/cm³
• LogP: 2.36390
• Storage Temp.: Store at RT
• Solubility.: DMSO: >10 mg/mL
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 304.18992602
• Heavy Atom Count: 22
• Complexity: 436

Purity/Quality:

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

DPCPX ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C3CCCC3
• Uses: DPCPX is a potent and very selective A1-adenosine receptor antagonist, with a Ki of 0.46 nM for A1 receptors in rat whole-brain membranes. Its 740-fold A1-selectivity is the highest reported for an adenosine antagonist 8-Cyclopentyl-1,3-dipropylxanthine has been used as an adenosine receptor (A1AR) antagonist in macrophages and human umbilical vein endothelial cells (HUVECs). It has also been used as A1AR antagonist in MCF-7 breast cancer cell line to test its anti-cancer effect.

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

There total 10 articles about 8-Cyclopentyl-1,3-dipropylxanthine 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: 93.0%

1,3-dipropyl-5-cyclopentanecarboxymido-6-aminouracil (112683-77-9) → 8-cyclopentyl-1,3-dipropylxanthine (102146-07-6)

Guidance literature:

With sodium hydroxide; In methanol; for 0.333333h; Heating;

DOI:10.1021/jm00398a020

Reference yield:

1,3-di-n-propyl-5-nitroso-6-aminouracil (81250-33-1) → 8-Cyclopentyl-1,3-dipropylxanthine (102146-07-6)

Guidance literature:

Multi-step reaction with 2 steps

1: LHMDS / tetrahydrofuran

2: Sn(OAc)2 / tetrahydrofuran / 48 h / Ambient temperature

With tin(II) acetate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1055/s-1999-3513

Reference yield:

6-amino-1,3-dipropyluracil (41862-14-0) → 8-Cyclopentyl-1,3-dipropylxanthine (102146-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaNO₂, AcOH / H₂O / 90 °C

2: H₂ / 5percent Pd/C / ethanol / 24 h / 3102.9 Torr

3: 130 °C

4: NaOH / H₂O / 1 h / Heating

With sodium hydroxide; hydrogen; acetic acid; sodium nitrite; palladium on activated charcoal; In ethanol; water;

DOI:10.1021/jm00108a029

upstream raw materials:

1,3-dipropyl-5-cyclopentanecarboxymido-6-aminouracil

Cyclopentanecarboxylic acid chloride

1,3-di-n-propyl-5-nitroso-6-aminouracil

1,3-dipropyl-5,6-diaminouracil

Refernces

• 1、 -. "Methods of treating pulmonary disease". . . Retrieved 2008/06/13.
• 2、 Shimada, Junichi,Suzuki, Fumio,Nonaka, Hiromi,Karasawa, Akira,Mizumoto, Hideaki,et al.. "8-(Dicyclopropylmethyl)-1,3-dipropylxanthine: A Potent and Selective Adenosine A1 Antagonist with Renal Protective and Diuretic Activities". . p. 466 - 469. Retrieved 2007/10/02.