1,3-Dipropyl-8-p-sulfophenylxanthine

Base Information

• Chemical Name: 1,3-Dipropyl-8-p-sulfophenylxanthine
• CAS No.: 89073-57-4
• Molecular Formula: C17H20 N4 O5 S
• Molecular Weight: 392.436
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70237528
• Nikkaji Number: J272.613K
• Wikidata: Q83119716
• ChEMBL ID: CHEMBL418333
• Mol file: 89073-57-4.mol

Synonyms:1,3-dipropyl-8-(4-sulfophenyl)xanthine;1,3-dipropyl-8-p-sulfophenylxanthine;1,3-dipropyl-8-sulfophenylxanthine;1,3-DSPX;DPSPX;PSPX

Chemical Property of 1,3-Dipropyl-8-p-sulfophenylxanthine

Chemical Property:

• Melting Point: >300°C
• Refractive Index: 1.6000 (estimate)
• PKA: -1.59±0.50(Predicted)
• PSA: 135.43000
• Density: 1.405g/cm³
• LogP: 2.70080
• Storage Temp.: Refrigerator
• Solubility.: H2O: 0.43 mg/mL
• Water Solubility.: 1.3g/L(temperature not stated)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 392.11544092
• Heavy Atom Count: 27
• Complexity: 671

Purity/Quality:

98%min ^*data from raw suppliers

1,3-Dipropyl-8-p-sulfophenylxanthine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C3=CC=C(C=C3)S(=O)(=O)O
• Uses: Water soluble adenosine receptor antagonist with slight selectivity for A1 receptors. Water soluble adenosine receptor antagonist with slight selectivity for A1 receptors

Technology Process of 1,3-Dipropyl-8-p-sulfophenylxanthine

There total 6 articles about 1,3-Dipropyl-8-p-sulfophenylxanthine 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-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonic acid 3-nitro-phenyl ester (666716-01-4) → meta-nitrophenol (554-84-7) + DPSPX (89073-57-4)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; at 37 ℃; Equilibrium constant;

DOI:10.1021/jm0310030

Reference yield:

1,3-dipropyl-6-amino-5-(p-sulfobenzamido)uracil (94781-79-0) → 1,3-dipropyl-8-(p-sulfophenyl)xanthine (89073-57-4)

Guidance literature:

With sodium hydroxide; at 70 ℃; for 0.0833333h; Yield given;

DOI:10.1021/jm00382a018

Reference yield:

6-amino-1,3-dipropyluracil (41862-14-0) → 1,3-dipropyl-8-(p-sulfophenyl)xanthine (89073-57-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / NaNO₂, 42percent acetic acid / H₂O / 0.25 h / pH 3

2: 83 percent / NaS₂O₄ / H₂O

3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / 1 h / Ambient temperature

4: 2.5N NaOH / 0.08 h / 70 °C

With sodium hydroxide; sodium dithionite; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite; In water;

DOI:10.1021/jm00382a018

upstream raw materials:

4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonic acid 3-nitro-phenyl ester

1,3-dipropyl-6-amino-5-(p-sulfobenzamido)uracil

1,3-dipropyl-5,6-diaminouracil

6-amino-1,3-dipropyluracil

Downstream raw materials:

N-<2-(dimethylamino)ethyl>-4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-dipropyl-1H-purin-8-yl)benzenesulfonamide

PD 113297

4-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonylamino]-butyric acid ethyl ester

N-(4-Dimethylamino-butyl)-4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonamide

Refernces

• 1、 Daly, J.W.,Padgett, W.,Shamim, M.T.,Butts-Lamb, P.,Waters, J.. "1,3-Dialkyl-8-(p-sulfophenyl)xanthines: Potent Water-Soluble Antagonistst for A1- and A2-Adenosine Receptors". . p. 487 - 492. Retrieved 2007/10/02.