Xanthine based N-heterocyclic carbene (NHC) complexes

Valdés, Hugo; Canseco‐González, Daniel; Germán-Acacio, Juan Manuel; Morales‐Morales, David

doi:10.1016/j.jorganchem.2018.01.008

Cited by 59 publications

(34 citation statements)

References 12 publications

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“…and silver(I), have attracted much attention for therapeutic applications. In fact, the easy functionalization of xanthines, combined with their biological activity, makes their metal derivatives excellent candidates for the development of novel metallodrugs [31]. Recently, we reported on a cationic gold(I) bis-NHC complex [Au(9-methylcaffein-8-ylidene)2] + (AuTMX2, Fig.…”

Section: Introductionmentioning

confidence: 99%

Comparative biological evaluation and G-quadruplex interaction studies of two new families of organometallic gold(I) complexes featuring N-heterocyclic carbene and alkynyl ligands

Meier‐Menches

Aikman

Döllerer

et al. 2020

Journal of Inorganic Biochemistry

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Experimental organometallic gold(I) compounds hold promise for anticancer therapy. This study reports the synthesis of two novel families of gold(I) complexes, including N1-substituted bis-Nheterocyclic carbene (NHCs) complexes of general formula [Au(N1-TBM)2]BF4 (N1-TBM = N1substituted 9-methyltheobromin-8-ylidene) and mixed gold(I) NHC-alkynyl complexes, [Au(N1-TBM)alkynyl]. The compounds were fully characterized for their structure and stability in aqueous environment and in the presence of N-acetyl cysteine by nuclear magnetic resonance (NMR)

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Section: Introductionmentioning

confidence: 99%

Comparative biological evaluation and G-quadruplex interaction studies of two new families of organometallic gold(I) complexes featuring N-heterocyclic carbene and alkynyl ligands

Meier‐Menches

Aikman

Döllerer

et al. 2020

Journal of Inorganic Biochemistry

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“…Therefore, the good reactivity of xanthines core along with their biological activity makes the metal derivatives excellent candidates for the development of novel metallodrugs. Moreover, depending on the kind of metal, several xanthine-NHC complexes are excellent catalysts for important organic reactions [45].…”

Section: Xanthine-nhc Complexesmentioning

confidence: 99%

Xanthine Scaffold: Available Synthesis Routes to Deliver Diversity by Derivatization

Petrucci

Feroci

Mattiello

et al. 2021

MROC

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: The functionalization of the skeletal systems of heterocycles represents a significant goal for new compounds development. The heterocyclic molecule xanthine (3,7-dihydro-1H-purine-2,6-dione) is a purine base with a bicyclic ring skeleton and four different nitrogen atoms, three of them are -NH groups. The principal derivatives are the well known natural methylxanthines (e.g. caffeine, theophylline and theobromine) that have prominent physiological effects at very low dose. The natural methylated xanthines, theophylline, theobromine and caffeine, are present in different plants such as the tea, cocoa and coffee species. For this reason natural xanthines can be considered as bio-based and renewable starting materials; their use in organic synthesis is strongly recommended in order to carry out sustainable chemistry. Essentially, the xanthine scaffold led to the preparation of numerous compounds very attractive in the pharmaceutical field, and these drugs are commercialized for a wide range of biological activities. The scope of this Mini Review is to consider the use of natural xanthines as starting material in chemical transformations carried out in organic solvents, without the intent to be exhaustive of all the synthetically chemical applications. More information on the chemical and electrochemical reactivity of this structural core in organic solvent can be useful for the scientific community. The effectiveness of natural xanthines can be improved by modifying the structures of these already biologically active compounds.

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“…The compounds are referred to as being blue copper(II) species, but an alleged X-ray structure (data neither shown in the publication nor deposited with the CCDC) and NMR spectroscopic data are clearly consistent with the presence of copper(I). A short review from 2018 summarizes the so far known chemistry of xanthine-based N -heterocyclic carbenes [ 38 ]. Given our interest in NHC-complexes of various metals and their biological activity and reactivity [ 39 , 40 , 41 , 42 , 43 , 44 ], we wished to develop more efficient methods to access a greater variety of xanthinium salts as well as their corresponding metal carbene-complexes.…”

Section: Introductionmentioning

confidence: 99%

Facile N9-Alkylation of Xanthine Derivatives and Their Use as Precursors for N-Heterocyclic Carbene Complexes

et al. 2021

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The xanthine-derivatives 1,3,7-trimethylxanthine, 1,3-dimethyl-7-benzylxanthine and 1,3-dimethyl-7-(4-chlorobenzyl)xanthine are readily ethylated at N9 using the cheap alkylating agents ethyl tosylate or diethyl sulfate. The resulting xanthinium tosylate or ethyl sulfate salts can be converted into the corresponding PF6- and chloride salts. The reaction of these xanthinium salts with silver(I) oxide results in the formation of different silver(I) carbene-complexes. In the presence of ammonia, ammine complexes [Ag(NHC)(NH3)]PF6 are formed, whilst with Et2NH, the bis(carbene) salts [Ag(NHC)2]PF6 were isolated. Using the xanthinium chloride salts neutral silver(I) carbenes [Ag(NHC)Cl] were prepared. These silver complexes were used in a variety of transmetallation reactions to give the corresponding gold(I), ruthenium(II) as well as rhodium(I) and rhodium(III) complexes. The compounds were characterized by various spectroscopic methods as well as X-ray diffraction.

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Xanthine based N-heterocyclic carbene (NHC) complexes

Cited by 59 publications

References 12 publications

Comparative biological evaluation and G-quadruplex interaction studies of two new families of organometallic gold(I) complexes featuring N-heterocyclic carbene and alkynyl ligands

Comparative biological evaluation and G-quadruplex interaction studies of two new families of organometallic gold(I) complexes featuring N-heterocyclic carbene and alkynyl ligands

Xanthine Scaffold: Available Synthesis Routes to Deliver Diversity by Derivatization

Facile N9-Alkylation of Xanthine Derivatives and Their Use as Precursors for N-Heterocyclic Carbene Complexes

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