Dyphylline

Base Information

• Chemical Name: Dyphylline
• CAS No.: 479-18-5
• Deprecated CAS: 52756-53-3,68350-70-9,68350-70-9
• Molecular Formula: C10H14N4O4
• Molecular Weight: 254.246
• Hs Code.: 29395900
• European Community (EC) Number: 207-526-1
• NSC Number: 756753,40844,14305
• UNII: 263T0E9RR9
• DSSTox Substance ID: DTXSID6022975
• Nikkaji Number: J2.054K
• Wikipedia: Diprophylline
• Wikidata: Q1073333
• NCI Thesaurus Code: C47504
• Pharos Ligand ID: GZ8Z6QHZ9L5Y
• Metabolomics Workbench ID: 145389
• ChEMBL ID: CHEMBL1752
• Mol file: 479-18-5.mol

Synonyms:Dihydroxypropyltheophylline;Dilin;Diphylline;Diprophylline;Dylix;Dyphylline;Lufyllin;Neothylline

Chemical Property of Dyphylline

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 9.57E-15mmHg at 25°C
• Melting Point: 161-162 °C(lit.)
• Refractive Index: 1.688
• Boiling Point: 589.6 °C at 760 mmHg
• PKA: 13.74±0.20(Predicted)
• Flash Point: 310.4 °C
• PSA: 102.28000
• Density: 1.57g/cm³
• LogP: -2.21310
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: Freely soluble in water, slightly soluble in ethanol (96 per cent).
• Water Solubility.: 33 g/100 mL (25 ºC)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 254.10150494
• Heavy Atom Count: 18
• Complexity: 364

Purity/Quality:

98%-102% ^*data from raw suppliers

Dyphylline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC(CO)O
• Description: Dyphylline is the N-7 dihydroxypropyl derivative of theophylline and is not a theophylline salt. Dyphylline does not get metabolized to theophylline in vivo, and even though it contains 70% theophylline by molecular weight ratio, the equivalent amount to theophylline is not known. Dosing must be accomplished independently by monitoring dyphylline blood levels. Dyphylline has a diminished bronchodilator effect compared to theophylline, but it may have lower and less serious side effects. Dosage forms available are an elixir and tablets. Dyphylline is a xanthine derivative that acts as an A1 and A2 adenosine receptor antagonist and phosphodiesterase inhibitor and exhibits bronchodilator and vasodilator effects. It also moderately inhibits microsomal prostaglandin E synthase-1 with an IC50 value of 200 μM and downregulates ABCG2 drug transporter expression in multidrug resistant tumor cells.
• Uses: PDE inhibitor, bronchodilator, vasodilator An adenosine receptor antagonist, phosphodiesterase inhibitor and vasodilator
• Therapeutic Function: Smooth muscle relaxant

Technology Process of Dyphylline

There total 17 articles about Dyphylline 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: 89.0%

theophylline (58-55-9,75448-53-2) + 3-Amino-1,2-propanediol (616-30-8,13552-31-3,98923-21-8) → diprophylline (479-18-5,52756-53-3)

Guidance literature:

theophylline; With potassium bisulfite; tin(ll) chloride; at 65 - 85 ℃; for 2h;

3-Amino-1,2-propanediol; at 55 ℃; for 2.66667h; Temperature;

Reference yield: 87.0%

7-allyl-1,3-dimethylxanthine (61444-26-6) → diprophylline (479-18-5,52756-53-3)

Guidance literature:

With dihydrogen peroxide; In formic acid;

Reference yield: 86.0%

(+/-)-3'-O-(p-toluoyl)dyphylline (1093252-48-2) → diprophylline (479-18-5,52756-53-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1080/15257770701845329

upstream raw materials:

theophylline

oxiranyl-methanol

3-monochloro-1,2-propanediol

1-bromo-2,3-propanediol

Downstream raw materials:

7-(2-hydroxy-3-trityloxy-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione

(+/-)-7-[(2-hydroxy-3-p-toluenesulfonyloxy)propyl]theophylline

1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl-acetaldehyd

(+/-)-3'-O-(p-toluoyl)dyphylline

Refernces

• 1、 Borowiecki, Pawe?,M?ynek, Mateusz,Dranka, Maciej. "Chemoenzymatic synthesis of enantiomerically enriched diprophylline and xanthinol nicotinate". . . Retrieved 2020/11/27.
• 2、 Ashry, El Sayed H. El,Awad, Laila F.,Rashed, Nagwa,AbdelRahman, Adel,Rasheed, Hana A.. "Synthesis and activity against HBV of novel tetra-seconucleoside analogues of dyphlline having the acyclic chains of ACV and HBG". . p. 309 - 317. Retrieved 2008/09/18.