961-45-5

Usage

Uses

Used in Pharmaceutical Industry:
8-PHENYLTHEOPHYLLINE is used as a non-selective adenosine receptor antagonist for its ability to prevent the anticonvulsant effect of curcumin. This property makes it a potential candidate for the development of drugs targeting adenosine receptors, which play a crucial role in various physiological processes, including the central nervous system, cardiovascular system, and immune system.
Additionally, due to its antagonistic effect on adenosine receptors, 8-PHENYLTHEOPHYLLINE may have potential applications in the treatment of various conditions, such as asthma, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, where adenosine receptor modulation can be beneficial. However, further research and clinical trials are necessary to establish its safety and efficacy in these applications.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 25, p. 495, 1977 DOI: 10.1248/cpb.25.495

InChI:InChI=1/C13H12N4O2/c1-16-11-9(12(18)17(2)13(16)19)14-10(15-11)8-6-4-3-5-7-8/h3-7H,1-2H3,(H,14,15)

Upstream product

• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 50996-28-6 1,3-dimethyl-5-oxy-6-phenyl-1H-pteridine-2,4-dione 
• 7136-10-9 1,3-diphenyl-2-iodo-3-chloropropan-1-one 
• 98-86-2 acetophenone 
• 84959-32-0 1,3-dimethyl-2-oxo-8-phenyl-1,2,3,7-tetrahydro-purine-6-thione S-oxide 
• 42963-36-0 4,6-dimethyl-<1,2,5>oxadiazolo<3,4-d>pyrimidine-5,7(4H,6H)-dione 1-oxide 
• 100-46-9 benzylamine 
• 538-51-2 benzylidene phenylamine 
• 60228-89-9 6-amino-1,3-dimethyl-5-{[1-phenylmeth-(E)-ylidene]-amino}-1H-pyrimidine-2,4-dione 
• 7033-39-8 5-bromo-1,3-dimethyluracil 
• 1670-14-0 benzamidine monohydrochloride 
• 109507-50-8 6-benzylamino-5-bromo-1,3-dimethyl-1H-pyrimidine-2,4-dione 

Downstream Products

• 62006-27-3 1,3-dimethyl-8-phenyl-6-thioxo-1,3,6,7-tetrahydro-purin-2-one 
• 83362-61-2 7-(2,3-Epoxypropyl)-8-phenyltheophylline 
• 6439-88-9 1,3,7-trimethyl-8-phenylxanthine 
• 36926-94-0 1,3-dimethyl-6-morpholin-4-yl-8-phenyl-1,3-dihydro-purin-2-one 

Relevant academic research and scientific papers

Cu-Catalyzed C-H Activation Reaction: One-Pot Direct Synthesis of Xanthine and Uric Acid Derivatives from 5-Bromouracil

A one-pot direct synthesis of xanthine and uric acid derivates is reported. This simple yet efficient methodology illustrates concurrent formation of two C-N bonds using CuBr 2as catalyst and one of those C-N bonds is formed by uracil C6-H bond activation.

Exploration of polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2- dihydroquinoline (PS-IIDQ) as new coupling agent for the synthesis of 8-substituted xanthine derivatives

Polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (PS-IIDQ), a polymer supported covalent coupling reagent, was successfully employed for the first time in the synthesis of 8-substituted xanthine derivatives. PS-IIDQ was observed

Synthesis of theophylline derivatives and study of their activity as antagonists at adenosine receptors

The synthesis of oligo(ethylene glycol)-alkene substituted theophyllines in positions 7 and/or 8 is described. The binding activity at adenosine receptors of selected derivatives was studied. Compound 2 showed high affinity for human A2B receptor (Ki = 4.16 nM) with a selectivity KiA2A/KiA2B of 24.1, and a solubility in water of 1 mM. The alkenyl substituent in some of the theophylline derivatives allows for covalent attachment of them onto hydrogen-terminated silicon substrate surfaces via hydrosilylation. Alternatively, an azido group was incorporated to an oligo(ethylene glycol)theophylline derivative as an anchor for tethering the molecules on ethynyl presenting surfaces via click reaction.

Dual inhibition of monoamine oxidase B and antagonism of the adenosine A2A receptor by (E,E)-8-(4-phenylbutadien-1-yl)caffeine analogues

The adenosine A2A receptor has emerged as an attractive target for the treatment of Parkinson's disease (PD). Evidence suggests that antagonists of the A2A receptor (A2A antagonists) may be neuroprotective and may help to alleviate the symptoms of PD. We have reported recently that several members of the (E)-8-styrylcaffeine class of A2A antagonists also are potent inhibitors of monoamine oxidase B (MAO-B). Since MAO-B inhibitors are known to possess anti-parkinsonian properties, dual-target-directed drugs that block both MAO-B and A2A receptors may have enhanced value in the management of PD. In an attempt to explore this concept further we have prepared three additional classes of C-8 substituted caffeinyl analogues. The 8-phenyl- and 8-benzylcaffeinyl analogues exhibited relatively weak MAO-B inhibition potencies while selected (E,E)-8-(4-phenylbutadien-1-yl)caffeinyl analogues were found to be exceptionally potent reversible MAO-B inhibitors with enzyme-inhibitor dissociation constants (Ki values) ranging from 17 to 149 nM. Furthermore, these (E,E)-8-(4-phenylbutadien-1-yl)caffeines acted as potent A2A antagonists with Ki values ranging from 59 to 153 nM. We conclude that the (E,E)-8-(4-phenylbutadien-1-yl)caffeines are a promising candidate class of dual-acting compounds.

Synthesis, DNA binding and antiviral activity of new uracil, xanthine, and pteridine derivatives

Some new 6-amino-1,3-dimethyl-5-(substituted methylidene)aminouracils were synthesized. Most of them were cyclized with triethyl orthoformate as a one-carbon source to afford 1,3-dimethyl-6-substituted pteridine derivatives. Certain uracils gave xanthine

Synthesis of purines and other fused imidazoles from acyclic amidines and guanidines

(Chemical Equation Presented) Purines, xanthines, and other fused imidazoles can be prepared from amidines or guanidines, with retrosynthetic disconnection at the ring fusion. Ring closure proceeds using Cu(I), with no special ligands required. The method allows for easy modification of the heterocyclic nucleus and is tolerant of functionality pendant to the ring system.

Synthesis of 8-substituted xanthine derivatives by Suzuki cross-coupling reaction

A Suzuki cross-coupling reaction procedure was developed to prepare 8-substituted 3,7-dihydropurine-2,6-dione (xanthine) derivatives. 8-Halogen-substituted xanthines were reacted with phenyl- and styrylboronic acids. The best results were obtained using tetrakis(triphenylphosphine)palladium(0) and tripotassium phosphate in dimethylformamide. The developed procedure allows for a convergent synthesis of pharmacologically active 8-substituted xanthine derivatives.

A high chemical reactivity of 5-azidouracils and its synthetic application: Novel synthesis of 8-substituted 1,3-dimethylxanthine derivatives

A novel method for the preparation of 8-substituted 1,3-dimethylxanthine derivatives (7 or 8) is described: treatment of 6-alkylamino-5-bromo-1,3-dimethyluracils (6a-e), easily prepared by brornination of the corresponding 6-alkyIamino-1,3-dimethyluracils (5), with sodium azide in DMF at ambient temperature allowed the direct formation of the 8-substituted 1,3-dimethylxanthines (7) proceeding via a transient formation of the corresponding 5-azido-1,3-dimethyluracils. The 5-bromo-1,3-dimethyluracils (6f, g) possessing an α-branched alkylamino group at the 6-position similarly react with sodium azide to afford 8,8-disubstituted 1,3-dimethyl-8H-xanthines (8,8-disubstituted 1,3-dimethyl-3,8-dihydropurine-2,6-diones)(8).

Xanthines, optionally incorporated in liposomes, for promoting skin or hair pigmentation

A method of treating skin or hair for promoting pigmentation wherein a xanthine component, in an amount effective to promote pigmentation, is incorporated in liposomes or hydrated lipidic lamellar phases.

Reactions of some 8-diazoxanthine derivatives

The coupling reaction of 8-diazo-1,3-dimethyl-(3) and 8-diazo-3-methyl-(4)-xanthines with some active methylene compounds does not give the triazine derivative (5); however, it gives new 8-azoxanthine derivatives (6-16).Nevertheless, compounds 3 and 4 undergo coupling reaction with secondary amines producing novel triazene derivatives (17-21).Heating of 3 with some dipolarophiles in benzene affords the unexpected 8-phenyltheophylline (24), which can be methylated to 8-phenylcaffeine (25). 8-Diazotheophylline (3) has been converted into 8-methoxy- and 8-ethoxy-theophyllines (26) and (27) by reaction with MeOH and EtOH, respectively.The reaction of 3 with 10percent HCl produces 8-chlorotheophylline (28).Structures of the compounds have been estabilished by elemental analyses and spectral data.