200557-53-5Relevant academic research and scientific papers
Construction of Dihydropyrido[2,3- d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes
Dzieszkowski, Krzysztof,Barańska, Izabela,Rafiński, Zbigniew
, p. 6645 - 6662 (2020/07/14)
N-Heterocyclic carbenes (NHCs) catalyzing aza-Claisen rearrangement of α,β-unsaturated enals with cyclic vinylogous amides under oxidative conditions generating potentially biologically active dihydropyridinone-fused uracils have been developed. This strategy represents a unique NHC-activation-based path with the use of 6-aminouracils as stable α,β-diEWG cyclic vinylogous amides for the efficient synthesis of bicyclic N-unprotected lactams similar to those in many useful drugs.
Novel adenosine A3 receptor modulators
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Page/Page column 16-17, (2008/06/13)
A class of novel antagonists for the adenosine A3 receptor are disclosed. These compounds are useful as therapeutic agents for a number of diseases and medical conditions that are mediated by the A3 receptor. The compounds of this in
Efficient synthesis of N-3-substituted 6-aminouracil derivatives, via N6-[(dimethylamino)methylene] protection
Priego,Camarasa,Pe?rez-Pe?rez
, p. 478 - 482 (2007/10/03)
A convenient synthetic procedure has been developed to introduce different functional groups at position 3 of 6-amino-1-benzyl- or 6-amino-1-methyluracil based on N6-[(dimethylamino) methylene] protection. This method allows for the smooth substitution at N-3 even when base-labile or heat sensitive halide reagents are employed.
A1 adenosine receptor antagonists as ligands for positron emission tomography (PET) and single-photon emission tomography (SPET).
Holschbach,Fein,Krummeich,Lewis,Wutz,Schwabe,Unterlugauer,Olsson
, p. 555 - 563 (2007/10/03)
The high affinity of 8-cyclopentyl-1,3-dipropylxanthine (CPX) for the A1 adenosine receptor (A1AR) provides a good lead for developing radioligands suitable for positron emission tomography (PET) and single-photon emission tomography (SPET). This study tested the hypothesis that the kinds of chemical modifications made in the synthesis of CPX analogues containing carbon-11, fluorine-18, or radioiodine will not alter affinity for the A1AR. This report describes the synthesis and radioligand binding assays of unlabeled CPX analogues having methyl, 2-methoxyethyl, 2-fluoropropyl, or 3-fluoropropyl substituents, respectively, at either N-1 (13a-d) or N-3 (8a-d) or an (E)-3-iodoprop-2-en-1-yl substituent at N-3 (8f). Compounds 8d,f and 13b,d antagonized the binding of [3H]CPX to the A1AR of rat brain with affinities similar to those of CPX; compound 8c was twice as potent as CPX. Analogues 8a,b and 13a were less potent than CPX, but for each the Ki of antagonism was > or = 0.5 nM. Attempts to iodinate the 8-(4-hydroxyphenyl) analogue of CPX failed, probably because the xanthine substituent strongly deactivated the phenol toward electrophilic iodination. In summary, several of the modifications of the propyl groups of CPX needed to produce ligands for imaging by PET and SPET preserve or enhance affinity for the A1AR.
PROCESS FOR PREPARING 1,3-DIPROPYL-8-(3-OXOCYCLOPENTYL)-XANTHINE
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, (2008/06/13)
A process for preparing 1,3-dipropyl-8-(3-oxocyclopentyl)-xanthine.
