Synthesis and Biological Evaluation of New Chromenes and Chromeno[2,3-d] pyrimidines

Belhadj, Fatima; Kibou, Zahira; Benabdallah, Mohammed; Aissaoui, Mohammed; Rahmoun, Mohammed Nadjib; Villemin, Didier; Choukchou‐Braham, Noureddine

doi:10.17159/0379-4350/2021/v75a18

Cited by 8 publications

References 27 publications

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Synthesis, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5‐Imino‐7‐Aryl‐5H‐Thiazolo[3.2‐a]Pyrimidine‐6‐Carbonitrile and Its Derivatives

Touati,

Benabdallah,

Merabat

et al. 2024

Journal of Heterocyclic Chem

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This study describes a simple, inexpensive, and effective method for the synthesis of new 5‐imino‐7‐aryle‐5H‐thiazolo[3,2‐a]pyrimidine‐3‐carbonitrile derivatives 4a‐e using a green procedure that does not require the use of heat or a base, creating a strategy that meets both economic and environmental demands. Various synthesized products were characterized via diverse techniques such as 1H‐NMR, infrared (FT‐IR), Mass spectroscopy (MS), and single crystal X‐ray diffraction. Using a fluorescence spectrometer, the 5‐imino‐7‐phenyle‐5H‐thiazolo[3.2‐a]pyrimidine‐3‐carbonitrile 4a has been tested as a potent fluorescent agent in mixture of DMSO/Water at 10−4 M in one hand, and on the other hand the results of our fluorescence evaluation studies with metal ions (Pb(II), Ba(II), Cd(II), Ni(II), Mn(II), Hg(II), Zn(II), Fe(II), Co(II), Cu(II), La(II), Cr(III), and Fe(III)) have shown that this compound exhibits a turn‐on and turn‐off of the fluorescence to 4a compound with these metals, what forms poor to good interaction by these ions. This result represents the emergence of a new potential ligand for the two heavy cations Cd(II) and Pb(II), which are toxic and polluting, and whose detection is currently of high interest. As well, In the molecular docking evaluation study, it was determined that the 4e molecule has an exceptional ability to inhibit the binding energy of the tubulin protein by −9.13 kcal/mmol, compared to other compounds. The results demonstrate the possibilities for a novel oral medication application.

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Synthesis, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5‐Imino‐7‐Aryl‐5H‐Thiazolo[3.2‐a]Pyrimidine‐6‐Carbonitrile and Its Derivatives

Touati,

Benabdallah,

Merabat

et al. 2024

Journal of Heterocyclic Chem

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Synthesis and Cytotoxic Evaluation of New Fluoro and Trifluoromethyl Substituents Containing Chromeno[2,3‐d]pyrimidines

et al. 2023

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In this research, microwave‐assisted “one‐pot” multicomponent reactions have been employed for the synthesis of new chromeno[2,3‐d]pyrimidines containing fluorine atoms. The biological significance of the obtained compounds was highlighted by evaluating in vitro for cytotoxic activity against four human cancer cell lines (HepG2, hepatoma carcinoma; MCF7, breast cancer; A549, non‐small lung cancer; KB, epidermoid carcinoma). Interestingly, two compounds revealed significant inhibitory activity against A549 cell line, and showed low toxicity to human embryonic kidney (Hek‐293) cell line. The synthetic efficacy and cytotoxic potency have offered an opportunity to further development of chromeno[2,3‐d]pyrimidines containing fluorine atoms as potential anticancer agents.

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Recent methods in the synthesis of chromeno[2,3-d]pyrimidines

Varala,

Kurra,

Amanullah

et al. 2024

Chem Heterocycl Comp

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Synthesis and Biological Evaluation of New Chromenes and Chromeno[2,3-d] pyrimidines

Cited by 8 publications

References 27 publications

Synthesis, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5‐Imino‐7‐Aryl‐5H‐Thiazolo[3.2‐a]Pyrimidine‐6‐Carbonitrile and Its Derivatives

Synthesis, Fluorescence Properties, Molecular Docking Studies, and Analysis of the Crystalline Structure of the Novel 5‐Imino‐7‐Aryl‐5H‐Thiazolo[3.2‐a]Pyrimidine‐6‐Carbonitrile and Its Derivatives

Synthesis and Cytotoxic Evaluation of New Fluoro and Trifluoromethyl Substituents Containing Chromeno[2,3‐d]pyrimidines

Recent methods in the synthesis of chromeno[2,3-d]pyrimidines

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