Adentri

Base Information

• Chemical Name: Adentri
• CAS No.: 166374-48-7
• Molecular Formula: C₁₈H₂₄N₄O₃
• Molecular Weight: 344.414
• Mol file: 166374-48-7.mol

Synonyms:1,3-dipropyl-8-(2-(5,6-epoxy)norbornyl)xanthine;1,3-ENX;Adentri;BG 9719;BG-9719;BG9719;CVT 124;CVT-124;ENX cpd

Chemical Property of Adentri

Chemical Property:

• Vapor Pressure: 3.57E-14mmHg at 25°C
• Boiling Point: 596.1°Cat760mmHg
• Flash Point: 314.3°C
• Density: 1.32g/cm³
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 344.18484064
• Heavy Atom Count: 25
• Complexity: 599

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C3CC4CC3C5C4O5
• Isomeric SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)[C@@H]3C[C@H]4C[C@@H]3[C@H]5[C@@H]4O5
• Recent EU Clinical Trials: A Randomised, Double-Blind, Placebo-Controlled, Parallel-Group Study to Assess the Safety and Tolerability of Oral Tonapofylline in Patients with Heart Failure and Renal Insufficiency

Technology Process of Adentri

There total 14 articles about Adentri 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: 66.0%

8-<(1S,2S)-5-Norbornen-2-yl>-1,3-dipropylxanthine (190316-05-3) → 1,3-dipropyl-8-[5,6-exo-epoxy-(1S,2S)-norbornan-2-yl]xanthine (190316-06-4,166374-48-7,166374-49-8)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In water; isopropyl alcohol; for 20h; Ambient temperature;

DOI:10.1021/jm970013w

Reference yield: 58.3%

1,3-dipropyl-8-((1R,2R)-5-norbornen-2-yl)xanthine (190316-03-1) → CVT-124 (166374-48-7,166374-49-8)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; In water; isopropyl alcohol; for 20h; Ambient temperature;

DOI:10.1021/jm970013w

Reference yield:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) → 1,3-dipropyl-8-[5,6-exo-epoxy-(1S,2S)-norbornan-2-yl]xanthine (190316-06-4,166374-48-7,166374-49-8)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl chloride / CH₂Cl₂ / 2 h / 20 °C

2: 14.5 g / Et₃N / tetrahydrofuran / 20 °C

3: 43 percent / aq. NaOH / methanol / 15 h / Heating

4: 44 percent / peracetic acid / CH₂Cl₂ / 16 h / 20 °C

5: tetrahydrofuran / 6 h / 45 - 50 °C / Irradiation

With peracetic acid; sodium hydroxide; oxalyl dichloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1081/SCC-120021980

upstream raw materials:

1,3-dipropyl-8-((1R,2R)-5-norbornen-2-yl)xanthine

5-norbornene-2-carboxylic acid

(1R,2R,4R)-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

5-norbornene-endo-2-carbonyl chloride

Refernces

• 1、 Chang, HeXi,Ensinger, Carol,McCargar, Robert D.,Vittimberga, Bruno M.. "Synthesis of an o-nitrobenzyl attached A1 adenosine receptor antagonist, a prodrug approach". . p. 2605 - 2611. Retrieved 2007/10/03.