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Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry
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Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry

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

Deadline for manuscript submissions: 31 August 2024 | Viewed by 8701

Special Issue Editor

Prof. Dr. Costel Moldoveanu

E-Mail Website
Guest Editor
Chemistry Department, Alexandru Ioan Cuza University of Iasi, 700506 Iasi, Romania
Interests: diazoles; medicinal chemistry; anticancer; antituberculosis; ultrasounds; microwave; organic synthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Heterocyclic compounds are such an important class of organic compounds that they have their own nomenclature and numbering system. The importance of these compounds derives from the fact that most heterocyclic compounds have biological activity. In fact, nucleic acids, which are the basis for the transmission of genetic information, are natural macromolecular compounds. The monomers from which these macromolecular compounds are derived have a nitrogenous base in their composition. Five heterocyclic compounds derived from purine (adenine and guanine) and pyrimidine (cytosine, thymine, and uracil) are known as nitrogenous bases.

The pharmaceutical industry and modern medicinal science put a lot of effort into their combat with two aggressive life-threatening diseases: cancer and tuberculosis (TB). Both diseases are leading causes of death worldwide, millions of people dying every year; the incidence of both are continually increasing, and the treatments become more and more complicated and sophisticated. The cancer chemotherapy is complex, expensive, and often rather inefficient, because of the large variety of neoplasm types, high toxicity levels, non-specificity of drugs, and the emergence of drug resistance and multidrug-resistance (MDR). On the other hand, because of the Mycobacterium tuberculosis (Mtb) versatility, the treatment against TB has become a challenging and difficult task, and the situation has become even worse because of the phenomena of drug resistance, MDR, extensively drug-resistant (XDR), association of TB with AIDS, etc. It is well known from the literature that imidazole (and its benzo-derivative benzimidazole) and pyridine (and its benzoderivative quinoline) derivatives are core scaffolds widely present in many classes of drugs (of natural or synthetic origin), displaying a large variety of interesting biological activities (antimicrobials, antifungus, anti-inflammatory, antihypertensive, antineuropathic, antihistaminic, etc.; anticancer and anti-TB are also included).

The aim of this Special Issue is to provide a platform to present the latest developments focused on the synthesis of biological active heterocycle derivatives especially (but not only) with anticancer, anti-tuberculosis, and antimicrobial properties.

Prof. Dr. Costel Moldoveanu
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

  • heterocycles
  • azines
  • azoles
  • anticancer
  • anti-tuberculosis
  • antimicrobial
  • growth factors

Published Papers (7 papers)

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Research

14 pages, 4460 KiB  
Article
Discovery of Dolutegravir Derivative against Liver Cancer via Inducing Autophagy and DNA Damage
by Xixi Hou, Dong Yan, Ziyuan Wu, Longfei Mao, Huili Wang, Yajie Guo and Jianxue Yang
Molecules 2024, 29(8), 1779; https://doi.org/10.3390/molecules29081779 - 13 Apr 2024
Viewed by 560
Abstract
We introduced a terminal alkyne into the core structure of dolutegravir, resulting in the synthesis of 34 novel dolutegravir-1,2,3-triazole compounds through click chemistry. These compounds exhibited remarkable inhibitory activities against two hepatocellular carcinoma cell lines, Huh7 and HepG2. Notably, compounds 5e and 5p [...] Read more.
We introduced a terminal alkyne into the core structure of dolutegravir, resulting in the synthesis of 34 novel dolutegravir-1,2,3-triazole compounds through click chemistry. These compounds exhibited remarkable inhibitory activities against two hepatocellular carcinoma cell lines, Huh7 and HepG2. Notably, compounds 5e and 5p demonstrated exceptional efficacy, particularly against Huh7 cells, with IC50 values of 2.64 and 5.42 μM. Additionally, both compounds induced apoptosis in Huh7 cells, suppressed tumor cell clone formation, and elevated reactive oxygen species (ROS) levels, further promoting tumor cell apoptosis. Furthermore, compounds 5e and 5p activated the LC3 signaling pathway, inducing autophagy, and triggered the γ-H2AX signaling pathway, resulting in DNA damage in tumor cells. Compound 5e exhibited low toxicity, highlighting its potential as a promising anti-tumor drug. Full article
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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20 pages, 4940 KiB  
Article
Designing Potent Anti-Cancer Agents: Synthesis and Molecular Docking Studies of Thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidine Derivatives
by Eman S. M. Elsenbawy, Zafer S. Alshehri, Nouf A. Babteen, Adel A.-H. Abdel-Rahman, Mai A. El-Manawaty, Eman S. Nossier, Reem K. Arafa and Nasser A. Hassan
Molecules 2024, 29(5), 1067; https://doi.org/10.3390/molecules29051067 - 29 Feb 2024
Viewed by 778
Abstract
A new series of thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines was designed and synthesized using readily available starting materials, specifically, β-enaminoester. Their cytotoxicity was screened against three cancer cell lines, namely, MCF-7, HCT-116, and PC-3. 2-(4-bromophenyl)triazole 10b and 2-(anthracen-9-yl)triazole 10e afforded excellent potency [...] Read more.
A new series of thieno[2,3-d][1,2,4]triazolo[1,5-a]pyrimidines was designed and synthesized using readily available starting materials, specifically, β-enaminoester. Their cytotoxicity was screened against three cancer cell lines, namely, MCF-7, HCT-116, and PC-3. 2-(4-bromophenyl)triazole 10b and 2-(anthracen-9-yl)triazole 10e afforded excellent potency against MCF-7 cell lines (IC50 = 19.4 ± 0.22 and 14.5 ± 0.30 μM, respectively) compared with doxorubicin (IC50 = 40.0 ± 3.9 μM). The latter derivatives 10b and 10e were further subjected to in silico ADME and docking simulation studies against EGFR and PI3K and could serve as ideal leads for additional modification in the field of anticancer research. Full article
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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16 pages, 1863 KiB  
Article
β-Nicotinamide Mononucleotide Promotes Cell Proliferation and Hair Growth by Reducing Oxidative Stress
by Chuntao Xu, Jiawei Dai, Hongxia Ai, Weian Du and Hongbing Ji
Molecules 2024, 29(4), 798; https://doi.org/10.3390/molecules29040798 - 08 Feb 2024
Viewed by 2020
Abstract
β-Nicotinamide mononucleotide (NMN) has shown promising effects on intestinal health, and it is extensively applied as an anti-aging and Alzheimer’s disease therapeutic, due to its medicinal properties. The effects of NMN on the growth of mouse hair were observed after hair removal. The [...] Read more.
β-Nicotinamide mononucleotide (NMN) has shown promising effects on intestinal health, and it is extensively applied as an anti-aging and Alzheimer’s disease therapeutic, due to its medicinal properties. The effects of NMN on the growth of mouse hair were observed after hair removal. The results indicated that NMN can reverse the state of hair follicle atrophy, hair thinning, and hair sparsity induced by dihydrotestosterone (DHT), compared to that of minoxidil. In addition, the action mechanisms of NMN promoting hair growth in cultured human dermal papilla cells (HDPCs) treated with DHT were investigated in detail. The incubation of HDPCs with DHT led to a decrease in cell viability and the release of inflammatory mediators, including interleukin-6 (IL-6), interleukin-1Beta (IL-1β) and tumor necrosis factor Alpha (TNF-α). It was found that NMN can significantly lower the release of inflammatory factors induced by DHT in HDPCs. HDPCs cells are protected from oxidative stress damage by NMN, which inhibits the NF-κB p65 inflammatory signaling pathway. Moreover, the levels of androgen receptor (AR), dickkopf-1 (DKK-1), and β-catenin in the HDPCs were assessed using PCR, indicating that NMN can significantly enhance the expression of VEGF, reduced IL-6 levels and suppress the expression of AR and DKK-1, and notably increase β-catenin expression in DHT-induced HDPCs. Full article
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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14 pages, 1209 KiB  
Article
5-Nitrofuran-Tagged Oxazolyl Pyrazolopiperidines: Synthesis and Activity against ESKAPE Pathogens
by Elizaveta Rogacheva, Lyudmila Kraeva, Alexey Lukin, Lyubov Vinogradova, Kristina Komarova, Mikhail Chudinov, Maxim Gureev and Evgeny Chupakhin
Molecules 2023, 28(18), 6491; https://doi.org/10.3390/molecules28186491 - 07 Sep 2023
Viewed by 682
Abstract
A series of eight 5-nitrofuran-tagged oxazolyl tetrahydropyrazolopyridines (THPPs) has been prepared in six stages with excellent regioselectivity. The testing of these compounds against pathogens of the ESKAPE panel showed a good activity of lead compound 1-(2-methoxyethyl)-5-(5-nitro-2-furoyl)-3-(1,3-oxazol-5-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c] pyridine (13g), which [...] Read more.
A series of eight 5-nitrofuran-tagged oxazolyl tetrahydropyrazolopyridines (THPPs) has been prepared in six stages with excellent regioselectivity. The testing of these compounds against pathogens of the ESKAPE panel showed a good activity of lead compound 1-(2-methoxyethyl)-5-(5-nitro-2-furoyl)-3-(1,3-oxazol-5-yl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c] pyridine (13g), which is superior to nitrofurantoin. These results confirmed the benefit of combining a THPP scaffold with a nitrofuran warhead. Certain structure–activity relationships were established in the course of this study which were rationalized by the induced-fit docking experiments in silico. Full article
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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21 pages, 2559 KiB  
Article
A New Way to 2,3,4-Trisubstituted Benzo[h]quinolines: Synthesis, Consecutive Reactions and Cellular Activities †
by Viktor A. Zapol’skii, Sandra Kaul, Bianka Karge, Mark Brönstrup, Mimoza Gjikaj and Dieter E. Kaufmann
Molecules 2023, 28(6), 2479; https://doi.org/10.3390/molecules28062479 - 08 Mar 2023
Viewed by 1231
Abstract
The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene provides the appropriate precursors for the synthesis of 2,3,4-trisubstituted benzo[h]quinolines. These heterocycles are easily accessible via a single-step reaction with naphthalen-1-amine or anthracen-1-amine as the precursor. Due to the steric bulk and high [...] Read more.
The reaction of mercaptoacetic acid esters with pentachloro-2-nitro-1,3-butadiene provides the appropriate precursors for the synthesis of 2,3,4-trisubstituted benzo[h]quinolines. These heterocycles are easily accessible via a single-step reaction with naphthalen-1-amine or anthracen-1-amine as the precursor. Due to the steric bulk and high electron density ring, the ring closure of benzo[h]quinolines takes place exclusively. Such highly substituted annelated pyridine systems can be modified in subsequent, selective reactions to build up new N-heterocycles with promising microbiological properties. The antibacterial and antiproliferative assays against four mammalian cell lines demonstrate that some of the sulfur-substituted benzo[h]quinoline analogs display potent phenotypic bioactivities in the single-digit micromolar range. Full article
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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13 pages, 2910 KiB  
Article
Construction of 5-(Alkylamino)-6-aryl/alkylpyrazine-2,3-dicarbonitriles via the One-Pot Reaction of Alkyl Isocyanides with Aryl/Alkyl Carbonyl Chlorides and Diaminomaleonitrile: Fluorescence and Antimicrobial Activity Evaluation
by Amal Al-Azmi and Elizabeth John
Molecules 2022, 27(23), 8278; https://doi.org/10.3390/molecules27238278 - 27 Nov 2022
Viewed by 1180
Abstract
5-(Alkylamino)-6-aryl/alkylpyrazine-2,3-dicarbonitriles were successfully synthesized in good to moderate yields by reacting alkyl isocyanides with aryl/alkyl carbonyl chlorides, followed by the addition of diaminomaleonitrile. The synthesized pyrazines were fully characterized in this investigation, and X-ray crystal structure analysis was performed on some derivatives. The [...] Read more.
5-(Alkylamino)-6-aryl/alkylpyrazine-2,3-dicarbonitriles were successfully synthesized in good to moderate yields by reacting alkyl isocyanides with aryl/alkyl carbonyl chlorides, followed by the addition of diaminomaleonitrile. The synthesized pyrazines were fully characterized in this investigation, and X-ray crystal structure analysis was performed on some derivatives. The antibacterial and antifungal activities of the newly synthesized pyrazine-2,3-dicarbonitriles were assessed in addition to their UV and fluorescence results. All the compounds showed similar UV–Vis spectral features with absorption peaks (λmax) around 267, 303, and 373 nm. Full article
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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14 pages, 1682 KiB  
Article
Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
by Lidia Lungu, Caleria Cucicova, Svetlana Blaja, Alexandru Ciocarlan, Ion Dragalin, Alic Barba, Nicoleta Vornicu, Elisabeta-Irina Geana, Ionel I. Mangalagiu and Aculina Aricu
Molecules 2022, 27(16), 5082; https://doi.org/10.3390/molecules27165082 - 10 Aug 2022
Cited by 2 | Viewed by 1290
Abstract
Based on some homodrimane carboxylic acids and their acyl chlorides, a series of fourteen 2-homodrimenyl-1,3-benzothiazoles, N-homodrimenoyl-2-amino-1,3-benzothiazoles, 4′-methyl-homodrimenoyl anilides and 4′-methyl-homodrimenthioyl anilides were synthesized and their biological activities were evaluated on five species of fungi (Aspergillus niger, Fusarium solani, Penicillium [...] Read more.
Based on some homodrimane carboxylic acids and their acyl chlorides, a series of fourteen 2-homodrimenyl-1,3-benzothiazoles, N-homodrimenoyl-2-amino-1,3-benzothiazoles, 4′-methyl-homodrimenoyl anilides and 4′-methyl-homodrimenthioyl anilides were synthesized and their biological activities were evaluated on five species of fungi (Aspergillus niger, Fusarium solani, Penicillium chrysogenum, P. frequentans, and Alternaria alternata) and two strains of bacteria (Bacillus sp. and Pseudomonas aeruginosa). The synthesis involved the decarboxylative cyclization, condensation and thionation of the said acids, anhydrides or their derivatives with 2-aminothiophenol, 2-aminobenzothiazole, p-toluidine and Lawesson’s reagent. As a result, together with the desired compounds, some unexpected products 8, 25, and 27 were obtained, and the structures and mechanisms for their formation have been proposed. Compounds 4, 9, and 25 showed higher antifungal and antibacterial activity compared to the standards caspofungin (MIC = 1.5 μg/mL) and kanamycin (MIC = 3.0 μg/mL), while compound 8 had comparable activities. In addition, compounds 6, 17, and 27 showed selective antifungal activity at MIC = 2.0, 0.25, and 1.0 μg/mL, respectively. Full article
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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