23146-06-7

Usage

InChI:InChI=1/C10H13BrN4O2/c1-13-8-7(9(16)14(2)10(13)17)15(6-12-8)5-3-4-11/h6H,3-5H2,1-2H3

Upstream product

• 58-55-9 theophylline 
• 109-64-8 1,3-dibromo-propane 
• 23146-04-5 7-(3-hydroxy-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 

Downstream Products

• 205504-06-9 sesquihydrate 
• 113418-56-7 Wy 49051 
• 23146-04-5 7-(3-hydroxy-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 

Relevant academic research and scientific papers

N-heterocyclic carbene-Pd(II) complex based on theophylline supported on Fe3O4@SiO2 nanoparticles: Highly active, durable and magnetically separable catalyst for green Suzuki-Miyaura and Sonogashira-Hagihara coupling reactions

In this paper, a novel heterogeneous palladium catalyst was synthesized by anchoring N-heterocyclic carbene-Pd(II) complex based on theophylline on magnetic Fe3O4@SiO2 nanoparticles. The synthesized magnetic composite was characterized by fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA), vibration sample magnetometry (VSM), transmission electron microscopy (TEM), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), N2 adsorption-desorption isotherm analysis (BET), UV–vis spectroscopy and elemental analysis. Also, loading content of palladium on the catalyst was measured by inductive coupled plasma (ICP) analysis. The synthesized catalyst was used successfully for the Suzuki cross-coupling reactions of various aryl halides (I, Br, Cl) with phenylboronic acids. This reaction was best performed in water as a green solvent in the presence of just 0.37–0.5 mol% of the catalyst at 60 °C. Also, we have reported this recyclable catalytic system as a stable phosphine-free Pd catalyst for the Sonogashira cross-coupling of aryl halides (I, Br, Cl) with terminal aromatic and aliphatic alkynes under solvent-free conditions. All coupling reactions proceeded with good to excellent yields. The catalyst showed good stability and was recovered and reused for eight reaction cycles without a significant loss in its catalytic activity. Also, the leaching of the catalyst has been examined by a hot filtration test and ICP-AES analysis.

Synthesis and characterization of theophylline-triazole and theophylline-triazole-coumarin based molecular hybrids

A series of novel theophylline-triazole and theophylline-coumarin conjugates linked via triazole moiety employing click chemistry has been synthesized and characterized by FT-IR, 1H and 13C NMR, and mass-spectral methods. The reaction was performed regioselectively by using copper sulfate and sodium ascorbate to give 1,2,3-triazoles through Cu(I)-catalyzed azide- alkyne cycloaddition.

Synthesis and characterization of novel 1,2,3-triazole-linked theophylline and coumarin s-triazines

A series of novel s-triazine-1,2,3-triazole-theophylline and s-triazine-1,2,3-triazole-coumarin generation-0 dendrimers has been synthesized and characterized by FT-IR, 1H and 13C NMR, and mass-spectral methods. Some selected compounds have been evaluated for antibacterial and antifungal activity against a variety of strains and for anti-cancer activity against 60 human cancer cell lines.

Characterization of 'mini-nucleotides' as P2X receptor agonists in rat cardiomyocyte cultures. An integrated synthetic, biochemical, and theoretical study

The design and synthesis of 'mini-nucleotides', based on a xanthine- alkyl phosphate scaffold, are described. The physiological effects of the new compounds were evaluated in rat cardiac cell culture regarding Ca2+ elevation and contractility. The results indicate biochemical and physiological profiles similar to those of ATP, although at higher concentrations. The biological target molecules of these 'mini-nucleotides' were identified by using selective P2-R and A1-R antagonists and P2-R subtype selective agonists. On the basis of these results and of experiments in Ca2+ free medium, in which [Ca2+](i) elevation was not observed, we concluded that interaction of the analogues is likely with P2X receptor subtypes, which causes Ca2+ influx. Theoretical calculations analyzing electronic effects within the series of xanthine-alkyl phosphates were performed on reduced models at quantum mechanical levels. Calculated dipole moment vectors, electrostatic potential maps, and volume parameters suggest an explanation for the activity or inactivity of the synthesized derivatives and predict a putative binding site environment for the active agonists. Xanthine-alkyl phosphate analogues proved to be selective agents for activation of P2X-R subtypes, whereas ATP activated all P2-R subtypes in cardiac cells. Therefore, these analogues may serve as prototypes of selective drugs aiming at cardiac disorders mediated through P2X receptors.

Theophylline derivatives as potential histamine H3-receptor antagonists

Previous results of histamine H3-receptors investigations allowed to formulate a general structure of H3-receptor antagonists. According to this model a series of compounds were obtained. As heterocycles they contained a theophylline moiety connected with a polar group (amine, ester, amide, and thiourea function) via an alkyl chain linked by a spacer to a lipophilic residue. The common distance between xanthine moiety and lipophilic rest was a six-link-chain. Selected compounds did not show significant H3-receptor antagonist activity and were weak antagonists at histamine H1-receptors.

New antihistamines: Substituted piperazine and piperidine derivatives as novel H1-antagonists

Structural manipulation of polycyclic piperazinyl imide serotonergic agents led to the synthesis of compound 8, 2-[4-[4-[bis(4- fluorophenyl)methyl]-1-piperazinyl]butyl]-4,4a,5,5a,6,6a-hexa-hydro-4,6- ethenocycloprop[f]isoindole-1,3(2H,3aH)-dione, which demonstrated good H1- antagonist activity. Substitution of a xanthinyl moiety for the polycyclic imide group led to the identification of novel xanthinyl-substituted piperazinyl and piperidinyl derivatives with potent antihistamine H1- activity without the undesirable antidopaminergic activity of 8. One compound, 24, 7-[3-[4-(diphenylmethoxy)-1-piperidinyl]propyl]-3,7-dihydro- 1,3-dimethyl-1H-pyrine-2,6-dione (WY-49051), is a potent, orally active H1- antagonist with a long duration of action and a favorable central nervous system profile.

Histamine H1 antagonists

Histamine H1 -receptor antagonists of the formula: STR1 where R1 is hydrogen or alkyl; one of R2 and R3 is alkyl and the other is STR2 where R4 is pyridin-2-yl, pyridin-4-yl, thienyl, or phenyl, any of which is optionally substituted by a halo, alkyl of 1 to 6 carbon atoms, nitro, trifluoromethyl, hydroxy or alkoxy of 1 to 6 carbon atoms substituent; and R5 is pyridin-2-yl, pyridin-4-yl or phenyl, any of which is optionally substituted by a halo, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, nitro or trifluoromethyl substituent.

HISTAMINE H1 ANTAGONISTS

N-Theophyllin-7-ylalkylene-N 1-(bis-p-fluorophenyl)methyl-piperazine derivatives as histamine H 1-antagonists.