Novel 1,3-dipropyl-8-(1-heteroarylmethyl-1H-pyrazol-4-yl)-xanthine derivatives as high affinity and selective A2B adenosine receptor antagonists

Elzein, Elfatih; Kalla, Rao; Li, Xiaofen; Perry, Thao; Parkhill, Eric Q.; Palle, Venkata P.; Varkhedkar, Vaibahv; Gimbel, Art; Zeng, Dewan; Lustig, David A.; Leung, Kwan; Zablocki, Jeff

doi:10.1016/j.bmcl.2005.10.002

Cited by 46 publications

(35 citation statements)

References 12 publications

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“…The reaction of 5-and 3-chloromethyl-1,2,4-oxadiazoles 358 and 359, respectively, with pyrazolyl-purine affords the corresponding derivatives 360 and 361 (Scheme 13.130) [187].…”

Section: Reactivity Of Substituentsmentioning

confidence: 99%

“…Another different general synthetic route is based on the 1,3-dipolar cycloaddition of nitrile oxides to nitriles, developed by Leandri (cycloaddition route) [180]. The cyclization of O-acylamidoximes is performed by heating them at their melting point [185], or at reflux in a high-boiling solvent (DMF [186], toluene [187], pyridine [188], ethanol [189], acetonitrile [190], glacial acetic acid at reflux) [191,192], eventually in the presence of a dehydrating agent (phosphorous pentoxide, phosphorus oxychloride, or acetic anhydride).…”

Section: Synthesismentioning

confidence: 99%

“…A wide variety of carboxylic acid derivatives can be used for the formation of Oacylated amidoximes, such as esters [196], acid chlorides [152,154,171,175,187,197], [197b, 152, 171, 198], including symmetrical acid anhydrides derived from amino acids [184c], and amino-acid activated as succinimides [183].…”

Section: Synthesismentioning

confidence: 99%

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Oxadiazoles

Romeo¹,

Chiacchio²

2011

Modern Heterocyclic Chemistry

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“…The reaction of 5-and 3-chloromethyl-1,2,4-oxadiazoles 358 and 359, respectively, with pyrazolyl-purine affords the corresponding derivatives 360 and 361 (Scheme 13.130) [187].…”

Section: Reactivity Of Substituentsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

See 1 more Smart Citation

Oxadiazoles

Romeo¹,

Chiacchio²

2011

Modern Heterocyclic Chemistry

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“…Similarly, a few 1,5-diarylpyrazole derivatives exhibit non-nucleoside HIV-1 reverse transcriptase inhibitory activity [14]. Corresponding arylpyrazole derivatives have been recently identified as high affinity and selective A2B adenosine receptor antagonists [15].…”

Section: Introductionmentioning

confidence: 99%

Manganese(III) Schiff-base complexes involving heterocyclic β-diketone and diethylene triamine

Modi

Patel

Thaker

2008

Journal of Coordination Chemistry

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Synthesis, spectral, thermal and coordination aspects of pentadentate Schiff-base complexes of the type [Mn(L)(X)] Á H 2 O [where H 2 L ¼ N,N 0 -diethylamine bis(1-phenyl-3-methyl-4-acetylimino-2-pyrazoline-5-ol) and X¼NCS, NO 3 , ClO 4 , CN or N 3 ] are reported. The Schiffbase ligand (H 2 L) and metal complexes have been characterized by elemental analysis, FT-IR, 1 H-NMR, magnetic measurements, molar conductivity measurements, electronic spectra, cyclic voltammetric and thermal studies. Magnetic moment values are close to 4.9 B.M. indicating high spin complexes lacking exchange interaction. Infrared spectral data suggest coordination of the secondary amino group making the ligand pentadentate. All complexes are electrochemically inactive, indicating high stability. Thermal decomposition of the Schiff-base complexes indicates loss of water of hydration and decomposition of the ligand. Kinetic parameters such as order of reaction (n) and the energy of activation (E a ) are reported using the Horowitz-Metzger method, indicating first order kinetics and giving the activation entropy (ÁS*), the activation enthalpy (ÁH*) and the free energy of activation (ÁG*).

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“…8,10,11 Some pyrazole derivatives were reported to possess high affinity and selectivity towards A 2b adenosine receptor antagonists. 12 Particularly, aryl pyrazoles are important in medicinal and pesticidal chemistry. 13 Some aryl pyrazoles were reported to have non-nucleoside HIV-1 reverse transcriptase inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

New pyrazole derivatives of potential biological activity

Farghaly¹,

Esmail²,

Abdel‐Hafez³

et al. 2012

Arkivoc

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5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxaldehyde (1) was reacted with hydrazine hydrate and thiosemicarbazide to afford the corresponding hydrazones 2 and thiosemicarbazones 4. The latter compounds were used to obtain the pyrazole derivatives 3, 5-7. A series of azines 8a-e were obtained by reacting 2 with aromatic aldehydes. Potassium permanganate oxidation of 1 gave the acid 9, which was transformed into the corresponding acid azide 11 then used to prepare diverse urea derivatives 13-18 via Curtius reaction.

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Novel 1,3-dipropyl-8-(1-heteroarylmethyl-1H-pyrazol-4-yl)-xanthine derivatives as high affinity and selective A2B adenosine receptor antagonists

Cited by 46 publications

References 12 publications

Oxadiazoles

Oxadiazoles

Manganese(III) Schiff-base complexes involving heterocyclic β-diketone and diethylene triamine

New pyrazole derivatives of potential biological activity

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