1H-Purine-2,6-dione, 8-(hexahydro-2,5-methanopentalen-3a(1H)-yl)-3,7-dihydro-1,3-dipropyl-

Base Information

• Chemical Name: 1H-Purine-2,6-dione, 8-(hexahydro-2,5-methanopentalen-3a(1H)-yl)-3,7-dihydro-1,3-dipropyl-
• CAS No.: 136199-02-5
• Deprecated CAS: 328896-63-5
• Molecular Formula: C₂₀H₂₈N₄O₂
• Molecular Weight: 356.468
• European Community (EC) Number: 663-792-2
• UNII: 7805S5HIHX
• NCI Thesaurus Code: C96195
• Mol file: 136199-02-5.mol

Synonyms:1,3-dipropyl-8-(3-noradamantyl)xanthine;1,3-DNAX;8-(3-noradamantyl)-1,3-dipropylxanthine;8-(noradamantan-3-yl)-1,3-dipropylxanthine;KW 3902;KW-3902;MK 7418;MK-7418;MK7418;rolofylline

Chemical Property of 1H-Purine-2,6-dione, 8-(hexahydro-2,5-methanopentalen-3a(1H)-yl)-3,7-dihydro-1,3-dipropyl-

Chemical Property:

• Vapor Pressure: 2.33E-13mmHg at 25°C
• Boiling Point: 578°Cat760mmHg
• PKA: 9.23±0.70(Predicted)
• Flash Point: 303.4°C
• PSA: 72.68000
• Density: 1.262g/cm³
• LogP: 2.78400
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 356.22122615
• Heavy Atom Count: 26
• Complexity: 609

Purity/Quality:

98%Min ^*data from raw suppliers

KW 3902 ^*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: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C34CC5CC(C3)CC4C5
• Isomeric SMILES: CCCN1C2=C(C(=O)N(C1=O)CCC)NC(=N2)C34C[C@@H]5C[C@H](C3)CC4C5
• Recent EU Clinical Trials: A multicentre, randomised, double-blind, placebo-controlled study of the effects of KW-3902 Injectable Emulsion on heart failure signs and symptoms and renal function in subjects with acute heart failure syndrome and renal impairment who are hospitalised for volume overload and require intravenous diuretic therapy.
• Description: KW 3902 is an antagonist of the adenosine A1 receptor (Ki = 0.19 nM). It displays 890-fold selectivity for A1 receptors over A2A receptors and has no activity at A3 receptors. KW 3902 less potently inhibits human organic anion transporter 1 (OAT1; Ki = 7.82 μM). KW 3902 exhibits renal protective effects during hypoxemia in rabbits.
• Uses: KW 3902 is an adenosine A1-receptor antagonist, which has recently been shown to alleviate axonopathy caused by human Tau ΔK280. KW 3902 can be considered for the development of a treatment towards hypometabolism and neuronal dysfunction associated with Tau-induced neurodegenerative diseases.

Technology Process of 1H-Purine-2,6-dione, 8-(hexahydro-2,5-methanopentalen-3a(1H)-yl)-3,7-dihydro-1,3-dipropyl-

There total 6 articles about 1H-Purine-2,6-dione, 8-(hexahydro-2,5-methanopentalen-3a(1H)-yl)-3,7-dihydro-1,3-dipropyl- 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: 100.0%

1,3-dipropyl-5,6-diaminouracil (81250-34-2) + 3-noradamantanecarboxylic acid (16200-53-6) → rolofylline (136199-02-5)

Guidance literature:

With thionyl chloride; In pyridine; methanol;

Reference yield:

3-noradamantanecarboxylic acid chloride (67064-09-9) → rolofylline (136199-02-5)

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:

Hexahydro-2,5-methano-pentalene-3a-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (136199-22-9) → rolofylline (136199-02-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 10h; Yield given; Heating;

DOI:10.1021/jm00083a018

upstream raw materials:

Hexahydro-2,5-methano-pentalene-3a-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

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

3-noradamantanecarboxylic acid chloride

1,3-dipropyl-5,6-diaminouracil

Refernces

• 1、 -. "XANTHINE DERIVATIVES". . . Retrieved 2008/06/13.