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Aromatic Heterocyclic Compounds: Synthesis, Reactivity and Applications

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

Deadline for manuscript submissions: 31 October 2025 | Viewed by 964

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Laboratoire Lorrain de Chimie Moléculaire (L.2.C.M.), Université de Lorraine, 57078 Metz, France
Interests: organic synthesis; synthetic organic chemistry; heterocyclic chemistry; pharmaceutical chemistry
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Special Issue Information

Dear Colleagues,

Aromatic heterocyclic compounds represent a large place in organic chemistry. Considered as bioisosters of benzene, they are often used to replace the latter ring when exploring variations in biological or pharmaceutical activities. Some interesting activities can result from the presence of the heteroatom(s) and new binding sites that appear for docking on receptors. This class of compounds can be synthesized directly with different functions depending on the starting material. On the other hand, using the very special reactivity of the nucleus, functions can be introduced afterward by classical electrophilic reactions or metalation. Depending on the heterocycle used, even aromatic nucleophilic reactions are possible.

Many natural compounds contain aromatic heterocyclic moiety. This presents a challenge for the total synthesis of these natural compounds. The presence of different heteroatoms in the nucleus presents another challenge to synthesis or reactivity studies of such derivatives. Aromatic heterocycles are also used as intermediates for the construction of non-heterocyclic compounds (Padwa, Boger, Katritzky…). In this case, the heterocycle, used as a pivotal compound, disappears in the final step.

This class of products finds application not only in the medicinal domain but also in polymer chemistry and in material science, among many others.

Due to the number of possible aromatic heterocycles that exist, they will always remain an interesting and challenging field of organic chemistry.

Dr. Gilbert Kirsch
Guest Editor

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Keywords

  • aromatic heterocycles with one heteroatom
  • aromatic heterocycles with two or more heteroatoms
  • condensed compounds containing an aromatic heterocycle
  • direct synthesis
  • synthesis using electrophilic or nucleophilic reactions, metalation and reactivity
  • applications of aromatic heterocyclic compounds

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Published Papers (1 paper)

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Research

18 pages, 1822 KiB  
Article
Pyrrolopyrimidines: Design, Synthesis and Antitumor Properties of Novel Tricyclic Pyrrolo [2,3-d]pyrimidine Derivatives
by Buer Song, Zarifa Murtazaeva, Lifei Nie, Rustamkhon Kuryazov, Shukhrat Gaybullaev, Chao Niu, Khurshed Bozorov, Haji Akber Aisa and Jiangyu Zhao
Molecules 2025, 30(14), 2917; https://doi.org/10.3390/molecules30142917 - 10 Jul 2025
Viewed by 735
Abstract
The pyrrolo[2,3-d]pyrimidine (7-deazapurine) scaffold is a unique heterocyclic system included in the composition of most nucleotides. In this study, series of the pyrrolo[2,3-d]pyrimidine-imines and 3-halo-substituted pyrrolo[2,3-d]pyrimidines were designed and prepared in high yields. Condensed pyrimidines [...] Read more.
The pyrrolo[2,3-d]pyrimidine (7-deazapurine) scaffold is a unique heterocyclic system included in the composition of most nucleotides. In this study, series of the pyrrolo[2,3-d]pyrimidine-imines and 3-halo-substituted pyrrolo[2,3-d]pyrimidines were designed and prepared in high yields. Condensed pyrimidines are obtained via carbonyl-amine condensation and carbon-halogen bond formation. Pyrrolo[2,3-d]pyrimidine-imines containing a bromine substituent at position C-4 of the phenyl ring and azepine side-ring exhibited superior antitumor activity on the colon cancer HT-29 cell line; IC50 values were 4.55 and 4.01 µM, respectively. These results revealed an interesting pattern, where condensed pyrimidinones containing an azepine ring demonstrated selective antitumor activity on the colon cancer cell line HT-29. In addition, the molecular docking results suggest that compound 8g provided a thorough understanding of its interactions with the DDR2 active site. This could pave the way for further development and optimization of DDR-targeting drugs, contributing to advancements in cancer therapeutics. This lead compound may serve as design templates for further studies. Full article
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