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Fused-Nitrogen-Containing Heterocycles (Second Edition)
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Fused-Nitrogen-Containing Heterocycles (Second Edition)

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

Deadline for manuscript submissions: closed (28 February 2025) | Viewed by 3528

Special Issue Editor

Dr. Stanislav Kafka

E-Mail Website
Guest Editor
Associate Professor, Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, 760 01 Zlin, Czech Republic
Interests: organic chemistry; nitrogen-containing heterocycles; reactivity; synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

I am delighted to announce the launch of the second edition of this Special Issue dedicated to Fused-Nitrogen-Containing Heterocycles, including new insights into chemical transformations and their mechanisms; preparation of new compounds; new synthetic methods; stereoselective syntheses; isolation, structure resolutions and total syntheses of natural substances; compounds with interesting or useful physical properties that include, for example, photochromism or fluorescence; the biological activity of compounds; potential drugs; etc.

Researchers are invited to contribute research articles and comprehensive reviews reflecting the latest progress in fused-nitrogen-containing heterocycles. We believe that this Special Issue of Molecules will attract the interest of the scientific community and contribute to the improvement and expansion of knowledge in the area of fused-nitrogen-containing heterocycles.

Dr. Stanislav Kafka
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

  • polyheterocyclic compounds
  • new synthetic approaches
  • reaction mechanism study
  • stereoselectivity
  • natural products
  • structure determination
  • absolute configuration
  • biological activity
  • structure–activity relationships
  • drug design

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Related Special Issue

Published Papers (3 papers)

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Research

27 pages, 1919 KiB  
Article
A Sustainable Synthesis of Novel 2-(3,4-Disubstituted phenyl)benzoxazole Derivatives and Their Antiproliferative and Antibacterial Evaluation
by Anja Rakas, Leentje Persoons, Dirk Daelemans, Dajana Kučić Grgić and Tatjana Gazivoda Kraljević
Molecules 2025, 30(8), 1767; https://doi.org/10.3390/molecules30081767 - 15 Apr 2025
Viewed by 279
Abstract
This study describes the synthesis of O-alkylated benzaldehydes 1–8, Schiff bases 9–28, and benzoxazole derivatives 29–48 using microwave, ultrasound, and mechanochemical reactions, as well as reactions in deep eutectic solvents in excellent yields, and [...] Read more.
This study describes the synthesis of O-alkylated benzaldehydes 1–8, Schiff bases 9–28, and benzoxazole derivatives 29–48 using microwave, ultrasound, and mechanochemical reactions, as well as reactions in deep eutectic solvents in excellent yields, and their antiproliferative and antibacterial activities. The in vitro evaluation of antiproliferative activity for the newly synthesised benzoxazole derivatives 29–48 against a diverse panel of human cancer cell lines, such as LN-229, Capan-1, HCT-116, NCI-H460, DND-41, HL-60, K-562, and Z-138 demonstrated that the majority of these benzoxazole derivatives displayed promising anticancer activity, particularly against non-small cell lung cancer (NSCLC) cells (NCI-H460). Notably, several derivatives showed enhanced activity compared to the included reference drug, etoposide. Considering the influence of substituents at position 5 of the benzoxazole ring and positions 3 and 4 of the phenyl ring on the antiproliferative activity, it is evident that derivatives 41–48 bearing a methoxy group at position 3 generally exhibit higher activity compared to compounds 29–40, which lack substitution at position 3. Furthermore, derivatives substituted at position 4 with a morpholine substituent, as well as those with an N,N-diethyl group, exhibited higher activity compared to other evaluated benzoxazole derivatives. The in vitro antibacterial evaluation against Gram-positive and Gram-negative bacteria revealed that benzoxazole derivative 47 exhibited notable activity, against the Gram-negative bacterium Pseudomonas aeruginosa (MIC = 0.25 μg/mL) and the Gram-positive bacterium Enterococcus faecalis (MIC = 0.5 μg/mL). The results point out that this class of benzoxazoles can be efficiently synthesized using eco-friendly methods and represent promising candidates for further design and optimization aimed at developing potent antiproliferative agents. Full article
(This article belongs to the Special Issue Fused-Nitrogen-Containing Heterocycles (Second Edition))
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16 pages, 2056 KiB  
Article
Synthesis and Antimicrobial Activity of 3-Alkylidene-2-Indolone Derivatives
by He Huang, Yating Zhang, Qiu Du, Changji Zheng, Chenghua Jin and Siqi Li
Molecules 2024, 29(22), 5384; https://doi.org/10.3390/molecules29225384 - 15 Nov 2024
Cited by 1 | Viewed by 1106
Abstract
The escalating threat of antibiotic-resistant bacteria and fungi underscores an urgent need for new antimicrobial agents. This study aimed to synthesize and evaluate the antimicrobial activities of two series of 3-alkylidene-2-indolone derivatives. We synthesized 32 target compounds, among which 25 exhibited moderate to [...] Read more.
The escalating threat of antibiotic-resistant bacteria and fungi underscores an urgent need for new antimicrobial agents. This study aimed to synthesize and evaluate the antimicrobial activities of two series of 3-alkylidene-2-indolone derivatives. We synthesized 32 target compounds, among which 25 exhibited moderate to high antibacterial or antifungal activities. Notably, compounds 10f, 10g, and 10h demonstrated the highest antibacterial activity with a minimum inhibitory concentration (MIC) of 0.5 μg/mL, matching the activity of the positive control gatifloxacin against three Gram-positive bacterial strains: Staphylococcus aureus ATCC 6538, 4220, and Methicillin-resistant Staphylococcus aureus ATCC 43300. Moreover, the three most active compounds 10f, 10g, and 10h were evaluated for their in vitro cytotoxicity in the HepG2 cancer cell line and L-02; only compound 10h was found to exert some level of cytotoxicity. These findings suggest that the synthesized 3-alkylidene-2-indolone derivatives hold potential for further development as antibacterial agents. Full article
(This article belongs to the Special Issue Fused-Nitrogen-Containing Heterocycles (Second Edition))
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20 pages, 11953 KiB  
Article
Protic Processes in an Extended Pyrazinacene: The Case of Dihydrotetradecaazaheptacene
by Aël Cador, Samia Kahlal, Gary J. Richards, Jean-François Halet and Jonathan P. Hill
Molecules 2024, 29(10), 2407; https://doi.org/10.3390/molecules29102407 - 20 May 2024
Viewed by 1253
Abstract
Pyrazinacenes are linearly fused heteroaromatic rings, with N atoms replacing all apical CH moieties. Component rings may exist in a reduced state, having NH groups instead of N, causing cross-conjugation. These compounds have interesting optical and electronic properties, including strong fluorescence in the [...] Read more.
Pyrazinacenes are linearly fused heteroaromatic rings, with N atoms replacing all apical CH moieties. Component rings may exist in a reduced state, having NH groups instead of N, causing cross-conjugation. These compounds have interesting optical and electronic properties, including strong fluorescence in the near-infrared region and photocatalytic properties, leading to diverse possible applications in bio-imaging and organic synthesis, as well as obvious molecular electronic uses. In this study, we investigated the behavior of seven-ring pyrazinacene 2,3,11,12-tetraphenyl-7,16-dihydro-1,4,5,6,7,8,9,12,13,14,15,16,17,18-tetradecaazaheptacene (Ph4H2N14HEPT), with an emphasis on protic processes, including oxidation, tautomerism, deprotonation, and protonation, and the species resulting from those processes. We used computational methods to optimize the structures of the different species and generate/compare molecular orbital structures. The aromaticity of the species generated by the different processes was assessed using the nucleus-independent chemical shifts, and trends in the values were associated with the different transformations of the pyrazinacene core. The computational data were compared with experimental data obtained from synthetic samples of the molecule tBu8Ph4H2N14HEPT. Full article
(This article belongs to the Special Issue Fused-Nitrogen-Containing Heterocycles (Second Edition))
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