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Molecules
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Synthesis and Applications of N-Heterocyclic Carbenes
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Synthesis and Applications of N-Heterocyclic Carbenes

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 July 2021) | Viewed by 5371

Special Issue Editor

Dr. Ana Petronilho

E-Mail Website
Guest Editor
Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, 2780-157 Oeiras, Portugal
Interests: N-Heterocyclic carbenes; nucleobases; transition metals; coordination chemistry; DNA methylation; anti-cancer agents; medicinal chemistry; catalysis

Special Issue Information

Dear Colleagues,

The importance of N-Heterocyclic carbenes (NHCs) as ligands for transition metal complexes is unquestionable, with well-known applications in catalysis, materials, and medicinal chemistry. The synthetic variability of these ligands makes them excellent scaffolds that enabling to tailor the electronic and steric properties of a given metal complex. This Special Issue is dedicated to the latest research on the synthesis and applications of NHCs. We welcome original research papers, review articles, and short communications that discuss novel synthetic methods, new ligand precursors, or advances in applications.

Dr. Ana Petronilho
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Catalysis
  • Synthesis
  • Carbenes
  • N-Heterocycles
 

Published Papers (2 papers)

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Research

14 pages, 2916 KiB  
Article
N-Heterocyclic Carbene Iron Complexes as Anticancer Agents: In Vitro and In Vivo Biological Studies
by Oscar A. Lenis-Rojas, Sandra Cordeiro, Marta Horta-Meireles, Jhonathan Angel Araujo Fernández, Sabela Fernández Vila, Juan Andrés Rubiolo, Pablo Cabezas-Sainz, Laura Sanchez, Alexandra R. Fernandes and Beatriz Royo
Molecules 2021, 26(18), 5535; https://doi.org/10.3390/molecules26185535 - 12 Sep 2021
Cited by 5 | Viewed by 2541
Abstract
Cisplatin and its derivatives are commonly used in chemotherapeutic treatments of cancer, even though they suffer from many toxic side effects. The problems that emerge from the use of these metal compounds led to the search for new complexes capable to overcome the [...] Read more.
Cisplatin and its derivatives are commonly used in chemotherapeutic treatments of cancer, even though they suffer from many toxic side effects. The problems that emerge from the use of these metal compounds led to the search for new complexes capable to overcome the toxic side effects. Here, we report the evaluation of the antiproliferative activity of Fe(II) cyclopentadienyl complexes bearing n-heterocyclic carbene ligands in tumour cells and their in vivo toxicological profile. The in vitro antiproliferative assays demonstrated that complex Fe1 displays the highest cytotoxic activity both in human colorectal carcinoma cells (HCT116) and ovarian carcinoma cells (A2780) with IC50 values in the low micromolar range. The antiproliferative effect of Fe1 was even higher than cisplatin. Interestingly, Fe1 showed low in vivo toxicity, and in vivo analyses of Fe1 and Fe2 compounds using colorectal HCT116 zebrafish xenograft showed that both reduce the proliferation of human HCT116 colorectal cancer cells in vivo. Full article
(This article belongs to the Special Issue Synthesis and Applications of N-Heterocyclic Carbenes)
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12 pages, 2416 KiB  
Article
Synthesis of Platinum(II) N-Heterocyclic Carbenes Based on Adenosine
by Maria Inês P. S. Leitão, Giulia Francescato, Clara S. B. Gomes and Ana Petronilho
Molecules 2021, 26(17), 5384; https://doi.org/10.3390/molecules26175384 - 4 Sep 2021
Cited by 4 | Viewed by 2021
Abstract
Organometallic derivatization of nucleosides is a highly promising strategy for the improvement of the therapeutic profile of nucleosides. Herein, a methodology for the synthesis of metalated adenosine with a deprotected ribose moiety is described. Platinum(II) N-heterocyclic carbene complexes based on adenosine were synthesized, [...] Read more.
Organometallic derivatization of nucleosides is a highly promising strategy for the improvement of the therapeutic profile of nucleosides. Herein, a methodology for the synthesis of metalated adenosine with a deprotected ribose moiety is described. Platinum(II) N-heterocyclic carbene complexes based on adenosine were synthesized, namely N-heterocyclic carbenes bearing a protected and unprotected ribose ring. Reaction of the 8-bromo-2′,3′,5′-tri-O-acetyladenosine with Pt(PPh3)4 by C8−Br oxidative addition yielded complex 1, with a PtII centre bonded to C-8 and an unprotonated N7. Complex 1 reacted at N7 with HBF4 or methyl iodide, yielding protic carbene 2 or methyl carbene 3, respectively. Deprotection of 1 to yield 4 was achieved with NH4OH. Deprotected compound 4 reacted at N7 with HCl solutions to yield protic NHC 5 or with methyl iodide yielding methyl carbene 6. Protic N-heterocyclic carbene 5 is not stable in DMSO solutions leading to the formation of compound 7, in which a bromide was replaced by chloride. The cis-influence of complexes 1–7 was examined by 31P{1H} and 195Pt NMR. Complexes 2, 3, 5, 6 and 7 induce a decrease of 1JPt,P of more than 300 Hz, as result of the higher cis-influence of the N-heterocyclic carbene when compared to the azolato ligand in 1 and 4. Full article
(This article belongs to the Special Issue Synthesis and Applications of N-Heterocyclic Carbenes)
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