A Simple Preparative Synthesis of Isomeric 2-Chloroquinolinecarboxylic Esters DOI Creative Commons

Yu. V. Ishkov,

V. V. Veduta, N. F. Fed’ko

et al.

Journal of organic and pharmaceutical chemistry, Journal Year: 2023, Volume and Issue: 21(4), P. 11 - 17

Published: Nov. 29, 2023

A simple two-stage method for the synthesis of isomeric esters 2-chloroquinoline-5-, 6-, 7-carboxylic acids by successive oxidation and chlorination reactions methyl quinoline-5-, 7-carboxylates has been developed. The target compounds have obtained in acceptable yields using readily available reagents, transformations, purification methods. Quinoline-8-carboxylic acid ester is unreactive under these conditions. 2-chloroquinoline-8-carboxylic with an overall yield 55%, starting from 8-methylquinoline. multi-stage process paid off fact that several transformations occur one reaction cycle. All methods developed can be used on a multigram scale. Intermediate 2(1H)-oxoquinoline carboxylates are promising functionalized condensed heterocycles.

Language: Английский

Synthesis and antibacterial medicinal evaluation of carbothioamido hydrazonyl thiazolylquinolone with multitargeting antimicrobial potential to combat increasingly global resistance DOI

Zhong‐Lin Zang,

Yi-Xin Wang,

Narsaiah Battini

et al.

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 275, P. 116626 - 116626

Published: June 27, 2024

Language: Английский

Citations

10
Cu-Catalyzed Tandem C–N and C–C Bond Formation Leading to 4(1H)-Quinolones: A Scaffold with Diverse Biological Properties from Totally New Raw Materials in a Single Step DOI
Satyanarayana Tummanapalli,

Kali Charan Gulipalli,

Srinu Bodige

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1609 - 1617

Published: Jan. 18, 2024

A novel Cu-catalyzed tandem C–N and C–C bond-formation reaction has been developed to furnish 2-substituted-4-(1H)-quinolones. 4-(1H)-quinolones play an important role in medicinal chemistry. Many 2-aryl(alkyl)-4(1H)-quinolones are found exhibit diverse biological properties. While traditional methods have inherent issues [like starting materials with incompatible functional groups (NH2 keto groups)], many modern either require activated (like Ynones) or employ expensive metals (Pd, Rh, Au, etc.) involving carbonylation using CO metal complexes. Our protocol presents environmentally friendly one-step method for the construction of these useful 2-substituted-4-(1H)-quinolones from easily available aryl boronic acid (or pinacolate ester) nitriles as new raw materials, a cheap Cu-catalyst O2 (air) green oxidant. We further extended its application synthesis various natural products, including first formal total punarnavine. plausible mechanism nitrilium ion (formed due intermolecular bond-forming coupling between boron species nitrile group) followed by intramolecular bond formation proposed.

Language: Английский

Citations

7
Synthesis, molecular docking analysis and in vitro evaluation of new heterocyclic hybrids of 4-aza-podophyllotoxin as potent cytotoxic agents DOI Creative Commons
Ha Thanh Nguyen,

Ket Tran Van,

Hai Pham‐The

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(3), P. 1838 - 1853

Published: Jan. 1, 2024

Two different synthetic approaches to novel heterocyclic hybrid compounds of 4-azapodophyllotoxin were investigated. The obtained products characterized by infrared spectroscopy, nuclear magnetic resonance and high-resolution mass spectrometry. MTT protocol was then performed examine the cytotoxic activity these against KB, HepG2, A549, MCF7, Hek-293 cell lines. assessment indicated that all displayed moderate high cytotoxicity tested cancer most active compound 13k containing 2-methoxypyridin-4-yl group exhibited selective HepG2 lines with IC50 values ranging from 0.23 0.27 μM, which between 5- 10-fold more potent than positive control ellipticine. Compounds 13a (HetAr = thiophen-3-yl) 13d 5-bromofuran-2-yl) selectivity for A549 when compared other low toxicity normal line. Molecular docking study conducted evaluate interaction new synthesized colchicine-binding-site tubulin. Besides that, physicochemical pharmacokinetic properties 13h,k predicted.

Language: Английский

Citations

3
Quinolin-4-ones: Methods of Synthesis and Application in Medicine DOI Creative Commons
Katarzyna Gach, Justyna Piekielna‐Ciesielska,

J. L. Waskiewicz

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(1), P. 163 - 163

Published: Jan. 3, 2025

Quinolinones, also called quinolones, are a group of heterocyclic compounds with broad spectrum biological activities. These occur naturally in plants and microorganisms but can be obtained synthetically. The first synthesis quinolinones took place at the end 19th century, most recent methods were published just few years ago. They allow for obtaining an unlimited number analogs differing properties. In this review, we described plethora leading to quinolin-4-ones. Several these have been used as antibiotics over four decades, recently, their antiproliferative effects particular interest researchers. This review summarizes experimental progress made synthetic development various routes quinoline-4-ones presents overview structures, evolution, relation activity.

Language: Английский

Citations

0
Exploring 4-quinolone-3-carboxamide derivatives: A versatile framework for emerging biological applications DOI
Joana Andrade, Thiago Mota do Vale,

R. Gomes

et al.

Bioorganic Chemistry, Journal Year: 2025, Volume and Issue: 157, P. 108240 - 108240

Published: Feb. 3, 2025

Language: Английский

Citations

0
An Overview of Quinolones as Potential Drugs: Synthesis, Reactivity and Biological Activities DOI Creative Commons
Ayoub El‐Mrabet, Amal Haoudi,

Youssef Kandri-Rodi

et al.

Organics, Journal Year: 2025, Volume and Issue: 6(2), P. 16 - 16

Published: April 3, 2025

Quinolones represent one of the largest classes synthetic antibiotics used in both human and veterinary medicine. Since discovery nalidixic acid, a substantial body research has been carried out on quinolones, resulting synthesis several quinolone derivatives with exceptional pharmacology. In addition to their antibacterial action, quinolones have broad spectrum diverse biological activities. this regard, present review examines literature recent years describing protocols, reactivity properties, particular emphasis antibacterial, antimalarial, antitrypanosomal, antileishmanial, antiviral anticancer activities famous class molecules. Finally, highlights potential as preferred pharmacophores medicinal chemistry. The aim is highlight innovative aspects rational design new therapeutic agents structural motif, face emerging antibiotic resistance urgent need for active

Language: Английский

Citations

0
Vistas in the domain of 3-acetyl-4-hydroxy-2-quinolinone derivatives (AHQ) and their applications DOI Creative Commons

Nedaa N. Elnaggar,

Wafaa S. Hamama, Eslam A. Ghaith

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(23), P. 18034 - 18088

Published: Jan. 1, 2025

This review discusses the significant advances in current status and latest synthesis techniques for N -substituted 3-acetyl-4-hydroxyquinolinones.

Language: Английский

Citations

0
Effective Synthesis of 4-Quinolones by Reductive Cyclization of 2′-Nitrochalcones Using Formic Acid as a CO Surrogate DOI Creative Commons
Francesco Ferretti,

Manar Ahmed Fouad,

Cecilia Abbo

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(14), P. 5424 - 5424

Published: July 15, 2023

4-Quinolones are the structural elements of many pharmaceutically active compounds. Although several approaches known for their synthesis, introduction an aryl ring in position 2 is problematic with most them. The reductive cyclization o-nitrochalcones by pressurized CO, catalyzed ruthenium or palladium complexes, has been previously reported to be a viable synthetic strategy this aim, but need CO lines and autoclaves prevented its widespread use. In paper, we describe use formic acid/acetic anhydride mixture as surrogate, which allows us perform reaction cheap commercially available thick-walled glass tube without adding any gaseous reagent. obtained yields often high compare favorably those CO. procedure was applied three-step synthesis from reagents alkaloid Graveoline.

Language: Английский

Citations

8
Quinolone Derivatives as Anticancer Agents: Importance in Medicinal Chemistry DOI
Nursyuhada Azzman, Sirajudheen Anwar, Wan Ahmad Syazani Mohamed

et al.

Current Topics in Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 24(13), P. 1134 - 1157

Published: April 9, 2024

Quinolone is a heterocyclic compound containing carbonyl at the C-2 or C-4 positions with nitrogen C-1 position. The scaffold was first identified for its antibacterial properties, and derivatives were known to possess many pharmacological activities, including anticancer. In this review, quinolin-2(H)-one quinolin-4(H)-one inhibit several various proteins enzymes involved in cancer cell growth, such as topoisomerase, microtubules, protein kinases, phosphoinositide 3-kinases (PI3K) histone deacetylase (HDAC). Hybrids of quinolone curcumin chalcone, 2-phenylpyrroloquinolin-4-one 4-quinolone have demonstrated strong potency against lines. Additionally, quinolones been explored inhibitors EGFR VEGFR. Therefore, review aims consolidate medicinal chemistry pipeline discuss their similarities terms pharmacokinetic profiles potential target sites provide an understanding structural requirements anticancer quinolones.

Language: Английский

Citations

2
One-Pot Synthesis of N-Fused Quinolone-4 Tetracyclic Scaffolds from 2,2-Disubstituted Indolin-3-ones DOI Creative Commons
Nikolai A. Arutiunov, Anna M. Zatsepilina, Anna A. Aksenova

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(45), P. 45501 - 45517

Published: Oct. 29, 2024

A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly complex (dihydro)indolo[1,2-a]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. latter can either be isolated good yields (75–96%) or, in case o-nitroacetophenone, used situ for further base-assisted intramolecular SNAr cyclization resulting indoxyl-fused quinolone-4 hybrids (up 95%).

Language: Английский

Citations

2