Design, synthesis, and cytotoxic activity of some novel N-(substituted) benzamide derivatives bearing coumarin and 1-azocoumarin compounds DOI Creative Commons
Ghaferah H. Al‐Hazmi

Bulletin of the Chemical Society of Ethiopia, Journal Year: 2023, Volume and Issue: 37(4), P. 1003 - 1019

Published: May 12, 2023

ABSTRACT. Among oxygen-containing heterocyclic compounds such as coumarin and azacoumarin derivatives, the scaffold has become an important construction motif for developing new drugs. Coumarin its derivatives possess many types of biological activities have been reported to show significant cytotoxic activity. N-(6,8-disubstituted coumarin-3-yl)benzamides (8a-c) namely (3-N-(benzoyl) aminocoumarin-6-ylmethyl acetate (8a); N-[6-(1-acetylpyrazol-3-yldiazineyl) coumarin-3-yl] benzamide (8b); N-(8-methoxy-6-bromo-coumarin-3-yl) (8c), were synthesized via a cyclocondensation reaction 5-(chloromethyl)-2-hydroxybenzaldehyde (3), 5-(pyrazol-3-yl-diazineyl)-2-hydroxybenzaldehyde (4), 5-bromo-3-methoxy- 2-hydroxybenzaldehyde (5) with N-benzoylglycine (7), in good yield. Treatment compound 8c ammonia presence anhydrous potassium carbonate yield N-(5-bromo-8-methoxy-1-azocoumarin-3-yl) (9). Compound (9) was acetylated acetic anhydride give N-(2-acetoxy-5-bromo-8-methoxyquinolin-3-yl) (10). N-(substituted azacoumarin-3-yl) benzamides (8-10) tested their vitro activity against (HepG2) cell line. Furthermore, DNA flow cytometry investigation over HepG2 cells indicated that 8a demonstrated arrest at G1/S stages cycle induction apoptosis by rising pre-G1 stage. displayed tubulin polymerization inhibition. KEY WORDS: Synthesis, Coumarin, Azacoumarin, Drugs, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(4), 1003-1019. DOI: https://dx.doi.org/10.4314/bcse.v37i4.16

Language: Английский

Design, Synthesis, and Biological Activities of Novel Coumarin Derivatives as Pesticide Candidates DOI

Henan Ma,

Kaihua Wang,

Beibei Wang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(9), P. 4658 - 4668

Published: Feb. 22, 2024

Food security is an important issue in the 21st century; preventing and controlling crop diseases pests are key to solve this problem. The creation of new pesticides based on natural products effective method. Herein, coumarins were selected as parent structures, a series their derivatives designed, synthesized, evaluated for antiviral activities, fungicidal insecticidal activities. We found that coumarin exhibited good excellent activities against tobacco mosaic virus (TMV). I-1, I-2a, I-4b, II-2c, II-2g, II-3, II-3b better than ribavirin at 500 μg/mL. Molecular docking research showed these compounds had strong interaction with TMV CP. These also broad-spectrum 14 plant pathogenic fungi. EC50 values I-3c, II-2d range 1.56–8.65 μg/mL Rhizoctonia cerealis, Physalospora piricola, Sclerotinia sclerotiorum, Pyricularia grisea. Most displayed Mythimna separata. Pesticide-likeness analysis following pesticide-likeness have potential be developed pesticide candidates. present work lays foundation discovery novel lead derivatives.

Language: Английский

Citations

22
Dietary Phenolic Compounds—Wellbeing and Perspective Applications DOI Open Access
Dasha Mihaylova, Maria Dimitrova-Dimova, Aneta Popova

et al.

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(9), P. 4769 - 4769

Published: April 27, 2024

Contemporary living is continuously leading to poor everyday choices resulting in the manifestation of various diseases. The benefits plant-based nutrition are undeniable and research on topic rising. Modern man now aware possibilities that plant can provide seeking ways benefit from it. Dietary phenolic compounds among easily accessible beneficial substances exhibit antioxidant, anti-inflammatory, antitumor, antibacterial, antiviral, antifungal, antiparasitic, analgesic, anti-diabetic, anti-atherogenic, antiproliferative, as well cardio-and neuroprotective activities. Several industries exploring incorporate biologically active their produce. This review concentrated presenting current information about dietary contribution maintaining good health. Additionally, this content will demonstrate importance prosperity natural for fields, i.e., food industry, cosmetology, biotechnology, others.

Language: Английский

Citations

14
An Overview on the Synthesis of Lamellarins and Related Compounds with Biological Interest DOI Creative Commons

Vasiliki-Panagiota M. Mitsiou,

Anastasia-Maria N. Antonaki,

Matina D. Douka

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(17), P. 4032 - 4032

Published: Aug. 26, 2024

Lamellarins are natural products with a [3,4]-fused pyrrolocoumarin skeleton possessing interesting biological properties. More than 70 members have been isolated from diverse marine organisms, such as sponges, ascidians, mollusks, and tunicates. There is continuous interest in the synthesis of these compounds. In this review, synthetic strategies for title compounds presented along their Three routes followed lamellarins. Initially, pyrrole derivatives starting or intermediate compounds, then they fused to isoquinoline coumarin moiety. Second, compound an indole last route, coumarins which moiety scaffold. The isolamellarins, azacoumestans, isoazacoumestans, analogues also described. above achieved via metal-catalyzed cross-coupling, [3 + 2] cycloaddition, substitution, lactonization reactions. exhibit cytotoxic, multidrug resistance (MDR), topoisomerase I-targeted antitumor, anti-HIV, antiproliferative, anti-neurodegenerative disease, anti-inflammatory activities.

Language: Английский

Citations

5
Elucidating the Mechanism of Coumarin Homodimerization Using 3-Acetylcoumarin Derivatives DOI Creative Commons
Kristina B. Simeonova, Ana I. Koleva, Nevena I. Petkova‐Yankova

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(3), P. 651 - 651

Published: Feb. 1, 2025

The current study is a continuation of our previous investigations into the radical homodimeric reaction mechanism 3-acetylcoumarin. In study, effects different substituents on coumarin ring 3-acetylcoumarin are investigated both experimentally and theoretically. Several derivatives (substituted at C-6, C-7, C-8) were tested in optimized conditions under ultrasound irradiation, biscoumarin species isolated characterized. elucidation substituent’s effect was further by means DFT calculations (free-energy calculations, NBO analysis), initial substituted coumarins formed radicals. It observed that presence C-6 C-8 positions moiety would not affect significantly formation radical, while group position C-7 could either stabilize or destabilize depending electronic properties substituent.

Language: Английский

Citations

0
De novo biosynthesis of the 4,6-dihydroxycoumarin in Escherichia coli DOI Creative Commons
Qi Gan, Tian Jiang, Chenyi Li

et al.

Green Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

By combining protein engineering and synthetic biology strategies, the novel de novo biosynthesis of 4,6-dihydroxycoumarin from glycerol was realized in Escherichia coli for first time.

Language: Английский

Citations

0
Pharmacochemical Studies of Synthesized Coumarin–Isoxazole–Pyridine Hybrids DOI Creative Commons

Matina D. Douka,

Ioanna Sigala, Catherine Gabriel

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(7), P. 1592 - 1592

Published: April 2, 2025

Several new coumarin–isoxazole–pyridine hybrids were synthesized through a 1,3-dipolar cycloaddition reaction of nitrile oxides, prepared in situ from pyridine aldehyde oximes, with propargyloxy- or propargylaminocoumarins moderate-to-good yields. Synthetic modifications applied using (diacetoxyiodo)benzene (PIDA) at room temperature, microwave irradiation, tert-butyl nitrite (TBN) under reflux. Coumarin, isoxazole, and groups selected for hybridization one molecule due to their biological impact inhibit lipid peroxidation an enzyme implicated inflammation. Preliminary vitro screening tests lipoxygenase (LOX) inhibition anti-lipid the performed. A discussion on structure–activity relationship is presented. Compounds 12b 13a found be potent LOX inhibitors IC50 5 μΜ 10 μΜ, respectively, while presented high (90.4%) peroxidation. Furthermore, exhibited moderate-to-low anticancer activities HeLa, HT-29, H1437 cancer cells.

Language: Английский

Citations

0
Anthelmintic and anti-filarial coumarins of natural and synthetic origin: Chemical and biological intervention DOI Creative Commons
Priyabrata Pattanayak,

Sudhanshu Sekhar Rout

Results in Chemistry, Journal Year: 2024, Volume and Issue: 7, P. 101327 - 101327

Published: Jan. 1, 2024

Coumarin is a bicyclic system with lactone-(hetero)aryl motif and critical structural unit of many natural synthetic pharmaceutical compounds. The coumarins possess broad spectrum biological activities have successful clinical applications. Several coumarin-based compounds like osthol, isopimpinellin, umbelliferon, scopoletin, scopoline, cleomiscosin A to D, inophyllum E been isolated anthelmintic antifilarial activities. ability coumarin interact various active sites through noncovalent interactions van der Waals forces, metal coordination, electrostatic hydrophobic interaction, as well hydrogen bonding, led the synthesis different significant anti-filarial SAR studies parasitic revealed that hydroxy group at C-4 C-7 positions has deciding role in activity. careful structure–activity could be effectively employed optimization ring, allowing it derivatives screened for helminthiases. We hope this review will provide structure-based input researchers design develop novel hybrids treat helminthiasis filariasis.

Language: Английский

Citations

2
Transition-Metal-Catalyzed Transformations for the Synthesis of Marine Drugs DOI Creative Commons

Lucía G. Parte,

Sergio Fernández,

Eva Sandonís

et al.

Marine Drugs, Journal Year: 2024, Volume and Issue: 22(6), P. 253 - 253

Published: May 29, 2024

Transition metal catalysis has contributed to the discovery of novel methodologies and preparation natural products, as well new chances increase chemical space in drug programs. In case marine drugs, this strategy been used achieve selective, sustainable efficient transformations, which cannot be obtained otherwise. perspective, we aim showcase how a variety transition metals have provided fruitful couplings wide drug-like scaffolds over past few years, by accelerating production these valuable molecules.

Language: Английский

Citations

2
Continuous Flow Chemistry: A Novel Technology for the Synthesis of Marine Drugs DOI Creative Commons
Laura Fernández-Peña, Paula González-Andrés,

Lucía G. Parte

et al.

Marine Drugs, Journal Year: 2023, Volume and Issue: 21(7), P. 402 - 402

Published: July 13, 2023

In this perspective, we showcase the benefits of continuous flow chemistry and photochemistry how these valuable tools have contributed to synthesis organic scaffolds from marine environment. These technologies not only facilitated previously described synthetic pathways, but also opened new opportunities in preparation novel molecules with remarkable pharmacological properties which can be used drug discovery programs.

Language: Английский

Citations

5
Synthesis of New of 4-Thiazolidinone and Thiazole Derivatives Containing Coumarin Moiety with Antimicrobial Activity DOI Creative Commons

Reem A. K. Al‐Harbi,

Marwa A.M.Sh. El‐Sharief, Samir Y. Abbas

et al.

Acta chimica slovenica, Journal Year: 2023, Volume and Issue: 70(4), P. 500 - 508

Published: Dec. 15, 2023

Synthesizing hybrid molecules is one the best manner to achieve novel promising agents. Consequently, series of new thiazoles having coumarin nucleus were synthesized from 3-acetylcoumarin thiosemicarbazones. Cyclization thiosemicarbazone derivatives with ethyl 2-chloroacetate, 1-chloropropan-2-one and 2-bromo-1-phenylethanone afforded corresponding 4-thiazolidinones, 4-methylthiazoles 4-phenylthiazoles, respectively. The expected antimicrobial propriety for thiazole investigated. thiosemicarbazones thiazolidin-4-ones showed moderate activities against G +ve -ve bacteria.

Language: Английский

Citations

4