261717-18-4

Basic information

• Product Name: MSX-2
• Synonyms: 3-(3-Hydroxypropyl)-8-(m-methoxystyryl)-7-methyl-1-propargylxanthine
• CAS NO: 261717-18-4
• Molecular Formula: C₂₁H₂₂N₄O₄
• Molecular Weight: 394.42
• Mol File: 261717-18-4.mol
• Article Data: 2

Chemical Properties

• Appearance: pale yellow/solid
• Storage Temp.: −20°C
• Solubility: DMSO: ~14 mg/mL
• CAS DataBase Reference: MSX-2(CAS DataBase Reference)
• NIST Chemistry Reference: MSX-2(261717-18-4)
• EPA Substance Registry System: MSX-2(261717-18-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 261717-18-4(Hazardous Substances Data)

Upstream product

• 6099-04-3 trans-3-methoxycinnamic acid 
• 702697-20-9 (E)-8-[2-(3-methoxyphenyl)vinyl]-1-prop-2-ynyl-3-(3-trimethylsilanyloxypropyl)-3,7-dihydropurine-2,6-dione 
• 261705-85-5 (E)-N-[6-amino-1-(3-hydroxypropyl)-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydropyrimidin-5-yl]-3-(3-methoxyphenyl)acrylamide 
• 261705-81-1 (E)-N-(6-amino-2,4-dioxo-3-prop-2-ynyl-1,2,3,4-tetrahydropyrimidin-5-yl)-3-(3-methoxyphenyl)acrylamide 
• 146830-70-8 6-amino-5-nitroso-3-prop-2-ynyl-1H,3H-pyrimidine-2,4-dione 
• 146830-75-3 5,6-diamino-3-prop-2-ynyl-1H,3H-pyrimidine-2,4-dione 
• 138895-22-4 6-amino-3-prop-2-ynyl-1H,3H-pyrimidine-2,4-dione 
• 702697-16-3 (E)-3-[8-[2-(3-methoxyphenyl)vinyl]-7-methyl-2,6-dioxo-1-prop-2-ynyl-1,2,6,7-tetrahydropurin-3-yl]propyl acetate 
• 261705-90-2 (E)-3-(3-hydroxypropyl)-8-[2-(3-methoxyphenyl)vinyl]-1-prop-2-ynyl-3,7-dihydropurine-2,6-dione 
• 74-88-4 methyl iodide 

Downstream Products

• 261705-78-6 di-O-tert-butyl 3-O-hydroxypropyl-8-(m-methoxystyryl)-7-methyl-1-propargylxanthine phosphate triester 
• 702697-21-0 (E)-3-(3-chloropropyl)-8-[2-(3-methoxyphenyl)vinyl]-7-methyl-1-prop-2-ynyl-3,7-dihydropurine-2,6-dione 

Relevant articles and documents

Multigram-Scale Syntheses, Stability, and Photoreactions of A2A Adenosine Receptor Antagonists with 8-Styrylxanthine Structure: Potential Drugs for Parkinson's Disease

The improved multigram-scale syntheses of the important 8-styrylxanthine A2A adenosine receptor antagonist MSX-2 (8), its water-soluble prodrug MXS-3 (9), and KW-6002 (16) are described. N-Alkylation reactions at different positions of uracil derivatives were optimized. Two different methods for xanthine formation from 6-amino-5-cinnainoylaminouracil precursors were investigated, (a) the elimination of water by alkaline catalysis and (b) hexamethyldisilazane as a condensing agent; the latter was found to be superior. The photosensitivity of 8-styrylxanthines was studied. The (E)-configurated stryrylxanthine MSX-2 (8) isomerized in diluted solution, and the resulting (Z)-isomer (10a) was isolated and characterized. Furthermore, we describe for the first time that solid 8-styrylxanthines can dimerize upon exposition to daylight or irradiation with UV light. The resulting cyclobutane derivatives with head-to-tail (syn) configuration exhibited a considerably lower A 2A adenosine receptor affinity than their parent compounds. The dimerization product of MSX-2 was a moderately potent nonselective A 1 and A2A antagonist (Ki(Ai) = 273 nM, Ki(A2A) = 175 nM) while the dimer of the related compound KW-6002 was inactive at A1 and only weakly active at A 2A adenosine receptors (Ki = 1.57 μM). The light sensitivity of 8-styrylxanthine derivatives, not only in solution, but also in the solid state, has to be considered when using those compounds as pharmacological tools or drugs.