Enzyme-catalysed one-pot synthesis of 4H-pyrimido[2,1-b] benzothiazoles and their application in subcellular imaging

Yu, Yuan; Zhang, Wei; Gong, Qing-Tian; Liu, Yanhong; Yang, Zeng‐Jie; He, Wei-Xun; Wang, Na; Yu, Xiao‐Qi

doi:10.1016/j.jbiotec.2020.09.014

Journal of Biotechnology

2020

DOI: 10.1016/j.jbiotec.2020.09.014

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Enzyme-catalysed one-pot synthesis of 4H-pyrimido[2,1-b] benzothiazoles and their application in subcellular imaging

Yuan Yu

Wei Zhang

Qing-Tian Gong

et al.

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Cited by 16 publications

References 45 publications

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Cu‐Catalyzed Synthesis of 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐ones: Molecular Docking Studies and Anti‐Proliferative Activities Against HepG2 Hepatocellular Carcinoma Cells

Aljaar,

Aboalrub,

Shtaiwi

et al. 2024

Asian J Org Chem

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The copper‐catalyzed regioselective domino synthesis of 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐ones 3 through N,S‐arylation strategies has been accomplished. This transformation was operated by the reaction of 1‐bromo‐2‐iodobenzenes 1 with 2‐thioxo‐2,3‐dihydropyrimidin‐4(1H)‐ones 2 in the presence of trans‐4‐hydroxy‐L‐proline as a ligand in DMSO as a solvent. Using this method, a library of diversely functionalized 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐one derivatives 3 were obtained in yields ranging 66‐85%. The described process revealed a very good tolerance to substituents on both 1‐bromo‐2‐iodobenzenes 1 and 2‐thioxo‐2,3‐dihydropyrimidin‐4(1H)‐ones 2. In addition, the reaction with 1,2‐diodobenzene yielded the corresponding 2‐methyl‐4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐one (3a) in 70% yield. Docking studies explained that the derivatives 3h, 3e, and 3p bind to the lipophilic pocket of the phosphoinositide 3‐kinase beta (PI3Kβ) and epidermal growth factor receptor (EGFR) with high affinities. In addition, the complex 3h‐4bfr formed a very stable complex with PI3Kβ with the lowest binding free energy of ‐7.89 kcal/mol. The anti‐proliferative activity against HepG2 hepatocellular carcinoma cells was evaluated using MTT assay. The compound 3h exhibited cytotoxic activity against HepG2 cells comparable to that of Erlotinib, a standard EGFR inhibitor (IC50 values of 19.1 and 14.7 µM). Four of the tested compounds (3e, 3f, 3o, and 3p) showed moderate anti‐proliferative activities (IC50 values of 53.9 to 92.2 µM).

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Cu‐Catalyzed Synthesis of 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐ones: Molecular Docking Studies and Anti‐Proliferative Activities Against HepG2 Hepatocellular Carcinoma Cells

Aljaar,

Aboalrub,

Shtaiwi

et al. 2024

Asian J Org Chem

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

Javahershenas,

Han,

Kazemi

et al. 2024

ChemistryOpen

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

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Recent Advances of AIEgens for Targeted Imaging of Subcellular Organelles

Song

Xiao

et al. 2021

Chem. Res. Chin. Univ.

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Enzyme-catalysed one-pot synthesis of 4H-pyrimido[2,1-b] benzothiazoles and their application in subcellular imaging

Cited by 16 publications

References 45 publications

Cu‐Catalyzed Synthesis of 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐ones: Molecular Docking Studies and Anti‐Proliferative Activities Against HepG2 Hepatocellular Carcinoma Cells

Cu‐Catalyzed Synthesis of 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐ones: Molecular Docking Studies and Anti‐Proliferative Activities Against HepG2 Hepatocellular Carcinoma Cells

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

Recent Advances of AIEgens for Targeted Imaging of Subcellular Organelles

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