1,4-Naphthoquinone Motif in the Synthesis of New Thiopyrano[2,3-<i>d</i>]thiazoles as Potential Biologically Active Compounds

A series of 11-substituted 3,5,10,11-tetrahydro-2<i>H</i>-benzo[6,7]thiochromeno[2,3-<i>d</i>][1,3]thiazole-2,5,10-triones were obtained via <i>hetero</i>-Diels-Alder reaction of 5-alkyl/arylallylidene/-4-thioxo-2-thiazolidinones and 1,4-naphthoquinones. The struc...

Full description

Bibliographic Details
Published in:	Molecules
Main Authors:	Andrii Lozynskyi, Julia Senkiv, Iryna Ivasechko, Nataliya Finiuk, Olga Klyuchivska, Nataliya Kashchak, Danylo Lesyk, Andriy Karkhut, Svyatoslav Polovkovych, Oksana Levytska, Olexandr Karpenko, Assyl Boshkayeva, Galiya Sayakova, Andrzej Gzella, Rostyslav Stoika, Roman Lesyk
Format:	Article
Language:	English
Published:	MDPI AG 2022-11-01
Subjects:	1,4-naphthoquinones <i>hetero</i>-Diels-Alder reaction thiopyrano[2,3-<i>d</i>]thiazoles X-ray anticancer activity cytotoxicity
Online Access:	https://www.mdpi.com/1420-3049/27/21/7575

Similar Items

Juglone-Bearing Thiopyrano[2,3-d]thiazoles Induce Apoptosis in Colorectal Adenocarcinoma Cells
by: Yuliia Kozak, et al.
Published: (2025-03-01)

<i>rel</i>-2-[4-Chloro-2-[(5<i>R</i>,6<i>R</i>,7<i>S</i>)-6-[5-(4-methoxyphenyl)-3-(2-naphthyl)-3,4-dihydropyrazole-2-carbonyl]-5-methyl-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-<i>d</i>]thiazol-7-yl]phenoxy]acetic Acid
by: Ihor Yushyn, et al.
Published: (2022-07-01)

Development of Novel Pyridine-Thiazole Hybrid Molecules as Potential Anticancer Agents
by: Iryna Ivasechko, et al.
Published: (2022-09-01)

Novel 1,2,4-Triazole- and Tetrazole-Containing 4<i>H</i>-Thiopyrano[2,3-<i>b</i>]quinolines: Synthesis Based on the Thio-Michael/aza-Morita–Baylis–Hillman Tandem Reaction and Investigation of Antiviral Activity
by: Andrey V. Khramchikhin, et al.
Published: (2023-11-01)

Drug design: 4-thiazolidinones applications. Part 1. Synthetic routes to the drug-like molecules
by: Roman Lesyk
Published: (2020-03-01)

Synthesis and Biological Evaluation of Novel 4-Morpholino-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine Derivatives Bearing Phenylpyridine/ Phenylpyrimidine-Carboxamides
by: Huimin Liu, et al.
Published: (2016-10-01)

Antineoplastic Activity of Water-Soluble Form of Novel Kinase Inhibitor 1-(4-Chlorobenzyl)-3-chloro-4-(3-trifluoromethylphenylamino)-1<i>H</i>-pyrrole-2,5-dione immobilized on Polymeric Poly(PEGMA-<i>co</i>-DMM) Carrier
by: Nataliya Finiuk, et al.
Published: (2022-01-01)

Surface Display of Human GM-CSF in Methylotrophic Yeasts
by: Olena Dmytruk, et al.
Published: (2025-09-01)

Synthesis, Characterization and In Vitro Evaluation of Novel 5-Ene-thiazolo[3,2-<i>b</i>][1,2,4]triazole-6(5<i>H</i>)-ones as Possible Anticancer Agents
by: Serhii Holota, et al.
Published: (2021-02-01)

Synthesis and Biological Activity Evaluation of Novel 5-Methyl-7-phenyl-3<i>H</i>-thiazolo[4,5-<i>b</i>]pyridin-2-ones
by: Andrii Lozynskyi, et al.
Published: (2021-11-01)

2-Amino-4,6,7,8-tetrahydrothiopyrano[3,2-b]pyran-3-carbonitrile 5,5-dioxide VP-4535 as an antimicrobial agent selective toward methicillin‐resistant Staphylococcus aureus
by: V. Palchykov, et al.
Published: (2022-02-01)

2-(Cyclopropylamino)-5-(4-methoxybenzylidene)thiazol-4(5<i>H</i>)-one
by: Ivan Sydorenko, et al.
Published: (2022-10-01)

Is Juglone the Only Naphthoquinone in <i>Juglans regia</i> L. with Allelopathic Effects?
by: Aljaz Medic, et al.
Published: (2021-08-01)

New thiopyrano[2,3-d][1,3]thiazole derivatives as potential antiviral agents
by: N. I. Zelisko, et al.
Published: (2016-04-01)

Plumbagin, a Potent Naphthoquinone from <i>Nepenthes</i> Plants with Growth Inhibiting and Larvicidal Activities
by: Asifur Rahman-Soad, et al.
Published: (2021-02-01)

Trastuzumab Potentiates Antitumor Activity of Thiopyrano[2,3-<i>d</i>]Thiazole Derivative in AGS Gastric Cancer Cells
by: Piotr Roszczenko, et al.
Published: (2024-10-01)

Bioactive Naphthoquinone and Phenazine Analogs from the Endophytic <i>Streptomyces</i> sp. PH9030 as α-Glucosidase Inhibitors
by: Qingxian Ma, et al.
Published: (2024-07-01)

Time-Dependent Degradation of Naphthoquinones and Phenolic Compounds in Walnut Husks
by: Aljaz Medic, et al.
Published: (2022-02-01)

Synthesis of thia-Michael-Type Adducts between Naphthoquinones and <i>N</i>-Acetyl-<i>L</i>-Cysteine and Their Biological Activity
by: Gabriele Micheletti, et al.
Published: (2022-09-01)

Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5<i>H</i>-pyrrolo[1,2-<i>a</i>]imidazole and 5<i>H</i>-Imidazo[1,2-<i>a</i>]azepine Quaternary Salts
by: Sergii Demchenko, et al.
Published: (2021-07-01)

Antifungal Activity of Selected Naphthoquinones and Their Synergistic Combination with Amphotericin B Against <i>Cryptococcus neoformans</i> H99
by: Naira Sulany Oliveira de Sousa, et al.
Published: (2025-06-01)

Targeting of the pro-oxidant-antioxidant balance in vitro and in vivo by 4-thiazolidinone-based chemotherapeutics with anticancer potential
by: L. Kobylinska, et al.
Published: (2019-04-01)

Synthesis of Spirooxindole-<em>O</em>-Naphthoquinone-Tetrazolo[1,5-<em>a</em>]Pyrimidine Hybrids as Potential Anticancer Agents
by: Liqiang Wu, et al.
Published: (2018-09-01)

Scolicidal and Apoptotic Activities of 5-hydroxy-1, 4-naphthoquinone as a Potent Agent against <i>Echinococcus granulosus</i> Protoscoleces
by: Masoud Moghadaszadeh, et al.
Published: (2021-06-01)

New Amino Naphthoquinone Derivatives as Anti-<i>Trypanosoma cruzi</i> Agents Targeting Trypanothione Reductase
by: Christian Espinosa-Bustos, et al.
Published: (2022-05-01)

Optimization of 1,4-Naphthoquinone Hit Compound: A Computational, Phenotypic, and In Vivo Screening against <i>Trypanosoma cruzi</i>
by: Leonardo S. Lara, et al.
Published: (2021-01-01)

Synthesis of 3,4-Dihydroxybenzoic Acid in <i>E. coli</i> and <i>C. glutamicum</i> Using Dehydroshikimate Dehydratase of Different Types
by: Ekaterina Shmonova, et al.
Published: (2025-08-01)

Antiparasitic Activity of <i>Plumbago auriculata</i> Extracts and Its Naphthoquinone Plumbagin against <i>Trypanosoma cruzi</i>
by: Raiza Brandão Peres, et al.
Published: (2023-05-01)

Jolanta Chwastyk-Kowalczyk: Londyński „Dziennik Polski i Dziennik Żołnierza” 1944-1989. Gazeta codzienna jako środek przekazu komunikatów kulturowych, Kielce 2008
by: Grażyna Gzella
Published: (2009-06-01)

Study of Androgenic Plant Families of Alloplasmic Introgression Lines (<i>H. vulgare</i>) –<i>T. aestivum</i> and the Use of Sister DH Lines in Breeding
by: Lidiya Pershina, et al.
Published: (2020-06-01)

Identification and Quantification of Naphthoquinones and Other Phenolic Compounds in Leaves, Petioles, Bark, Roots, and Buds of <i>Juglans regia</i> L., Using HPLC-MS/MS
by: Aljaz Medic, et al.
Published: (2021-09-01)

Narrating Conversion in Augustine’s <i>Notes on Job</i>
by: Nataliya D. Pratsovyta
Published: (2025-07-01)

An Annotated Checklist of Algae from the Order Synurales (Chrysophyceae) of Viet Nam
by: Evgeniy Gusev, et al.
Published: (2023-01-01)

<i>Bacillus subtilis</i> RBT-7/32 and <i>Bacillus licheniformis</i> RBT-11/17 as New Promising Strains for Use in Probiotic Feed Additives
by: Vera Yaderets, et al.
Published: (2023-11-01)

Characterization of Phytochemical Components of <i>Crocus sativus</i> Leaves: A New Attractive By-Product
by: Olha Mykhailenko, et al.
Published: (2021-06-01)

Inhibition of the Growth and Development of <i>Sclerotinia sclerotiorum</i> (Lib.) De Bary by Combining Azoxystrobin, <i>Penicillium chrysogenum</i> VKM F-4876d, and <i>Bacillus</i> Strains
by: Vera V. Yaderets, et al.
Published: (2021-12-01)

<i>Trichocladium solani</i> sp. nov.—A New Pathogen on Potato Tubers Causing Yellow Rot
by: Arseniy Belosokhov, et al.
Published: (2022-11-01)

Molecular Study of <i>Theileria annulata</i> and <i>Anaplasma</i> spp. in Ixodid Ticks from Southern Regions of the Republic of Kazakhstan
by: Zaure Z. Sayakova, et al.
Published: (2025-09-01)

Baker’s Yeast-Based Microbial Fuel Cell Mediated by 2-Methyl-1,4-Naphthoquinone
by: Juste Rozene, et al.
Published: (2021-03-01)

Metabolomic Profiling Reveals Differences in Hypoxia Response between Far Eastern and Siberian Frogs
by: Sergei V. Shekhovtsov, et al.
Published: (2023-10-01)