Recent Advances in the Application of 2‐Aminobenzothiazole to the Multicomponent Synthesis of Heterocycles

ChemistryOpen, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 9, 2024

Abstract Heterocycles are a vital class of compounds in numerous fields, including drug discovery, agriculture, and materials science. Efficient methods for the synthesis heterocycles remain critical meeting demands these industries. Recent advances multicomponent reactions (MCRs) utilizing 2‐aminobenzothiazole (ABT) have shown promising results formation heterocycles. The versatility this context has enabled rapid efficient construction diverse heterocyclic structures. Various synthetic methodologies involving discussed, highlighting its importance as valuable building block complex potential applications discovery material science also explored. Overall, review provides comprehensive overview current state research field offers insights into future directions area study. We highlight ABT versatile sustainable starting via MCRs, with significant implications chemical industry.

Language: Английский

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Enantioselective Synthesis of Axially Chiral Diaryl Ethers via NHC Catalyzed Desymmetrization and Following Resolution

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(4)

Published: Nov. 29, 2023

Axially chiral diaryl ethers are present in numerous natural products and bioactive molecules. However, only few catalytic enantioselective approaches have been established to access ether atropisomers. Herein, we report the N-heterocyclic carbene-catalyzed synthesis of axially via desymmetrization prochiral 2-aryloxyisophthalaldehydes with aliphatic alcohols, phenol derivatives, heteroaromatic amines. This reaction features mild conditions, good functional group tolerance, broad substrate scope excellent enantioselectivity. The utility this methodology is illustrated by late-stage functionalization, gram-scale synthesis, diverse enantioretentive transformations. Control experiments DFT calculations support association NHC-catalyzed following kinetic resolution enhance

Language: Английский

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Identification of Benzothiazoles Bearing 1,3,4-Thiadiazole as Antiproliferative Hybrids Targeting VEGFR-2 and BRAF Kinase: Design, Synthesis, BIO Evaluation and In Silico Study

Molecules, Journal Year: 2024, Volume and Issue: 29(13), P. 3186 - 3186

Published: July 4, 2024

Cancer remains a leading cause of death worldwide, often resulting from uncontrolled growth in various organs. Protein kinase inhibitors represent an important class targeted cancer therapies. Recently, the kinases BRAF and VEGFR-2 have shown synergistic effects on tumor progression. Seeking to develop dual BRAF/VEGFR-2 inhibitors, we synthesized 18 amino-benzothiazole derivatives with structural similarities reported inhibitors. Four compounds-

Language: Английский

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Benzothiazole a privileged scaffold for Cutting-Edges anticancer agents: Exploring drug design, structure-activity relationship, and docking studies

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 279, P. 116831 - 116831

Published: Sept. 6, 2024

Language: Английский

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Thioamides in medicinal chemistry and as small molecule therapeutic agents

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 277, P. 116732 - 116732

Published: Aug. 5, 2024

Language: Английский

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Neurobehavioral toxic effects and mechanisms of 2-aminobenzothiazole exposure on zebrafish

The Science of The Total Environment, Journal Year: 2023, Volume and Issue: 913, P. 169495 - 169495

Published: Dec. 22, 2023

2-Aminobenzothiazole (NTH), a benzothiazole derivative, exhibits potent biochemical activities and plays significant role in modern industry. Widespread intensive utilization of NTH has led to its detection aquatic environments, encompassing both groundwater surface water. Despite wide usage, the effect on developmental neurotoxicity organisms remains uncharted. Therefore, aim this investigation was create exposure models for short- long-term studies order analyze neurobehavioral toxic impact (0, 50, 500, 5000 μg/L) zebrafish, which includes motor function, anxiety, memory performance, as well examine mechanism neurotoxicity. The results revealed suppression initial embryonic mobility by NTH. However, during short-term experiments, it did not significantly functions zebrafish. In addition, effects zebrafish were observed after 50 500 μg/L NTH, mainly impacting locomotion, social behavior, cognitive functions. Moreover, caused oxidative damage adult brain tissue, accompanied abnormal expression damage-related genes. Furthermore, Real-Time PCR indicated genes related specifically those GABA synthesis pathway (gabrg2, gad2, gad1b, abat) 5-HT (tph2, tph1b, pet1, htr1aa). Taken together, study demonstrates first time that chronic decreases associated with pathway. This is damage, ultimately resulting changes ability, performance.

Language: Английский

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Novel 2-Aminobenzothiazole Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

ACS Omega, Journal Year: 2024, Volume and Issue: 9(12), P. 13928 - 13950

Published: March 14, 2024

Sixteen novel 2-aminobenzothiazole compounds with different amines or substituted piperazine moieties were designed, synthesized, and tested using various methods. Potential interactions assessed by docking new in the adenosine triphosphate (ATP) binding domain of PI3Kγ enzyme (PDB code: 7JWE) nucleophilic substitution solvent-free/neat fusion for docked compound synthesis. Final characterized direct probe gas chromatography-mass spectrometry (GC-MS), proton (1H-NMR), carbon-13 (13C-NMR), attenuated total reflectance-infrared Fourier transform infrared (ATR FT-IR). The synthesized investigated anticancer activities on lung cancer (A549) breast (MCF-7) cell lines. compounds' inhibition was evaluated at a 100 μM concentration. 4-Nitroaniline piperazine-4-nitroaniline combination OMS5 OMS14 reduced line growth. IC50 values OMS14, strongest compounds, ranged from 22.13 to 61.03 μM. OMS1 OMS2 inhibited highest rates (47 48%, respectively) Results show that suppression is not main mechanism behind these effects. CDK2, Akt, mTOR, p42/44 MAPK are affected. EGF receptor matters. AKT1, AKT3, CDK1/cyclin B, PDK1 direct, PIK3CA E542 K/PIK3R1 (p110 α/p85 α), PIK3CD/PIK3R1 δ/p85 PKN measured evaluate possible OMS14. α) most, 65% inhibition, suggesting properties. Furthermore, NCI 60-cell demonstrates promising broad against numerous lines which could be good lead future development.

Language: Английский

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Exploring β-carboline hybrids and their derivatives: A review on synthesis and anticancer efficiency

European Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: 288, P. 117412 - 117412

Published: Feb. 18, 2025

Language: Английский

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2-(Diarylalkyl)Aminobenzothiazole Derivatives Induce Autophagy And Apoptotic Death Through SIRT Inhibition And P53 Activation In MCF7 Breast Cancer Cells

Computational Biology and Chemistry, Journal Year: 2025, Volume and Issue: 116, P. 108395 - 108395

Published: Feb. 21, 2025

Language: Английский

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Novel transition metal (II) complexes of hydrazones as potential antitumor agents: Synthesis, characterization, DFT computations, cytotoxic activities, molecular docking and simulation studies

Inorganica Chimica Acta, Journal Year: 2025, Volume and Issue: unknown, P. 122634 - 122634

Published: March 1, 2025

Language: Английский

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