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Molbank
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Quinoline, Derivatives and Applications
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Quinoline, Derivatives and Applications

A special issue of Molbank (ISSN 1422-8599). This special issue belongs to the section "Organic Synthesis and Biosynthesis".

Deadline for manuscript submissions: closed (31 March 2022) | Viewed by 16892

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,

Quinoline synthons represent building blocks in a huge number of natural as well as synthetic molecules. A large number of them exhibit interesting biological effects and some of them found application as drugs, pesticides, or insecticides. Quinoline derivatives are also utilized in the areas of food, catalysts, dyes, smart materials, refineries, electronics, etc. Therefore, there is a high demand for the synthesis of quinoline derivatives. Besides the development of new methods for the construction of the quinoline scaffold, the functionalization of the quinoline structure has also gained great interest. Investigation of the reactivity of quinoline derivatives is incessantly relevant, as it steadily yields interesting, often surprising, results.

This Special Issue is focused on short papers describing novel synthetic approaches to quinoline derivatives and new processes for the preparation of substances by their transformation, while the quinoline pattern does not have to be preserved in the molecule of product.

Assoc. Prof. Dr. Stanislav Kafka
Guest Editor

Manuscript Submission Information

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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. Molbank is an international peer-reviewed open access quarterly 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 500 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

  • quinoline derivatives synthesis
  • novel synthetic strategies
  • reaction mechanism
  • natural compounds isolation
  • alkaloids
  • structure analysis
  • spectroscopic properties
  • functional materials
  • biologically active compounds
  • drug design

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Published Papers (6 papers)

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Research

6 pages, 811 KiB  
Communication
Ultrasonic Synthesis and Preliminary Evaluation of Anticoronaviral Activity of 6,7-Dimethoxy-4-(4-(4-methoxyphenyl)piperazin-1-yl)-1-methylquinolin-1-ium Iodide
by Aleksey A. Vasilev, Peter P. Grozdanov, Ivanka Nikolova, Valentin S. Lozanov and Meglena I. Kandinska
Molbank 2022, 2022(3), M1400; https://doi.org/10.3390/M1400 - 4 Jul 2022
Viewed by 1728
Abstract
Quinoline scaffold is one of the most intensively utilized pharmacophores in drug design because of the variety of activities demonstrated by different quinoline-based therapeutics or drug-candidates. Herein, we describe an environmentally tolerant two-step procedure as a convenient synthetic approach to novel chloroquine and [...] Read more.
Quinoline scaffold is one of the most intensively utilized pharmacophores in drug design because of the variety of activities demonstrated by different quinoline-based therapeutics or drug-candidates. Herein, we describe an environmentally tolerant two-step procedure as a convenient synthetic approach to novel chloroquine and hydroxychloroquine analogues. The structures of the newly synthesized compounds are estimated by 1H NMR, 13C NMR, LC-MS spectrometry and IR spectroscopy. Full article
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
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6 pages, 732 KiB  
Communication
Synthesis of 8-Aminoquinoline Amides of Ursonic and Oleanonic Acid
by Vladislavs Kroškins, Jevgeņija Lugiņina, Anatoly Mishnev and Māris Turks
Molbank 2022, 2022(2), M1361; https://doi.org/10.3390/M1361 - 11 May 2022
Cited by 1 | Viewed by 2222
Abstract
8-Aminoquinoline amides of 3-oxo-olean-12-en-28-oic acid and 3-oxo-urs-12-en-28-oic acid were obtained and characterized by 1H, 13C-NMR and single crystal X-ray analysis. The used triterpenoic acids are oxidized forms of naturally occurring oleanolic acid and ursolic acids. Such types of derivatives are known [...] Read more.
8-Aminoquinoline amides of 3-oxo-olean-12-en-28-oic acid and 3-oxo-urs-12-en-28-oic acid were obtained and characterized by 1H, 13C-NMR and single crystal X-ray analysis. The used triterpenoic acids are oxidized forms of naturally occurring oleanolic acid and ursolic acids. Such types of derivatives are known for their anticancer and antiviral activities. On the other hand, 8-aminoquinoline amides are frequently used for transition metal complexation that is applicable for both C-H activation processes and biological activity studies. Full article
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
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9 pages, 2139 KiB  
Communication
A Concise Synthesis towards Antimalarial Quinazolinedione TCMDC-125133 and Its Anti-Proliferative Activity against MCF-7
by Sitthivut Charoensutthivarakul, Duangporn Lohawittayanan, Phongthon Kanjanasirirat, Kedchin Jearawuttanakul, Sawinee Seemakhan, Suparerk Borwornpinyo and Matthew Phanchana
Molbank 2022, 2022(2), M1358; https://doi.org/10.3390/M1358 - 21 Apr 2022
Cited by 3 | Viewed by 2895
Abstract
Quinazolinedione is one of the most notable pharmacophores in drug discovery due to its broad spectrum of biological activities including antimalarial, anticancer, anti-inflammatory, and others. TCMDC-125133, whose structure features a quinazolinedione core, exhibits promising antimalarial activity and low toxicity as described in the [...] Read more.
Quinazolinedione is one of the most notable pharmacophores in drug discovery due to its broad spectrum of biological activities including antimalarial, anticancer, anti-inflammatory, and others. TCMDC-125133, whose structure features a quinazolinedione core, exhibits promising antimalarial activity and low toxicity as described in the GlaxoSmithKline (GSK) report. Herein, a concise four-step synthesis towards quinazolinedione TCMDC-125133 is described using low cost goods and greener alternatives where possible. All synthesized compounds were characterized using polarimetry, IR, NMR, and mass spectrometry. The in-house synthesized TCMDC-125133 was evaluated for its antimalarial activity against P. falciparum 3D7 and antiproliferative activity against MCF-7 cell line. Full article
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
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Graphical abstract

12 pages, 1759 KiB  
Communication
Synthesis of New 1,2,3,4-Tetrahydroquinoline Hybrid of Ibuprofen and Its Biological Evaluation
by Stanimir Manolov, Iliyan Ivanov and Dimitar Bojilov
Molbank 2022, 2022(1), M1350; https://doi.org/10.3390/M1350 - 7 Mar 2022
Cited by 7 | Viewed by 3440
Abstract
Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) were screened for their in vitro antioxidant, antitryptic, and inhibition of albumin denaturation activity. The lipophilicity was established [...] Read more.
Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) were screened for their in vitro antioxidant, antitryptic, and inhibition of albumin denaturation activity. The lipophilicity was established using both reversed-phase thin layer chromatography and in silico calculations. Full article
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
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Graphical abstract

7 pages, 575 KiB  
Communication
4-Amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline
by Peter G. Larson and David M. Ferguson
Molbank 2021, 2021(4), M1305; https://doi.org/10.3390/M1305 - 9 Dec 2021
Cited by 3 | Viewed by 2447
Abstract
4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in [...] Read more.
4-Amino-imidazo-, oxazolo-, and thiazoloquinolines are key structural scaffolds in the design of nucleoside base analogs for use as therapeutic agents. Current strategies for arriving at diverse substitutions at the C6–C9 positions of the thiazolo- and oxazoloquinolines, however, are limited due to difficulties in arriving at the thiazoloquinoline-5N-oxide intermediate using electron deficient aromatic systems. Here, we demonstrate a synthetic route to obtain substituted thiazoloquinolines with electron-withdrawing groups at the C7 position. The target compound, 4-amino-2-butyl-7-methoxycarbonylthiazolo[4,5-c]quinoline, is obtained in eight steps using a 7-bromo surrogate as a precursor to the successful generation of the N-oxide intermediate, and final transformation via Pd-mediated C7-acylation. Full article
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
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Graphical abstract

5 pages, 953 KiB  
Short Note
(2S*,4S*)-4-[(E)-(2,2-Dimethylhydrazono)methyl]-6-methoxy-4-methyl-2-[(E)-styryl]-1,2,3,4-tetrahydroquinoline
by José Clerigué, M. Teresa Ramos and J. Carlos Menéndez
Molbank 2021, 2021(2), M1220; https://doi.org/10.3390/M1220 - 1 Jun 2021
Cited by 1 | Viewed by 2139
Abstract
The Povarov reaction of p-anisidine, cinnamaldehyde and methacrolein dimethylhydrazone afforded a 1,2,3,4-tetrahydroquinoline derivative bearing 2-styryl, 4-methyl and 4-dimethylhydrazono substituents in a fully diastereoselective fashion. This is the first example of the combination of a type I aza-vinylogous Povarov reaction and a type [...] Read more.
The Povarov reaction of p-anisidine, cinnamaldehyde and methacrolein dimethylhydrazone afforded a 1,2,3,4-tetrahydroquinoline derivative bearing 2-styryl, 4-methyl and 4-dimethylhydrazono substituents in a fully diastereoselective fashion. This is the first example of the combination of a type I aza-vinylogous Povarov reaction and a type II vinylogous Povarov reaction in the same process. Full article
(This article belongs to the Special Issue Quinoline, Derivatives and Applications)
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