Green synthesis and histo-toxicological study of 2,3-dihydroquinazolin-4(1H)-ones catalysed by novel cellulose supported Bronsted acidic ionic liquid

IF 5.3 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Liquids Pub Date : 2025-04-21 DOI:10.1016/j.molliq.2025.127636

Dipak P. Hiwarale , Wilson B. Chandane , Nagesh B. Birajdar , Vikas D. Sonawane , Satyanarayan M. Arde , Sandip M. Deshmukh , Sandip S. Gare , Dattatraya G. Raut , Jayashree S. Kshirsagar , Gajanan S. Rashinkar , Shivanand G. Sonkamble

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引用次数: 0

Abstract

The present study highlights a green synthetic protocol for the efficient synthesis of bioactive 2,3-dihydroquinazolin-4(1H)-ones utilizing a novel cellulose-supported Bronsted acidic ionic liquid [Cell-Al₂O₃-Pr-Imi-Bu-SO₃H]Cl (7). The prepared catalyst was characterized by FT-IR, TGA, DTG, EDX analysis and EDX mapping, BET, powder XRD and FE-SEM techniques. Moreover, it was employed in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones via one-pot three-component condensation of isatoic anhydride, aryl aldehydes and ammonium acetate using ethanol as a green solvent. The synthesized 2,3-dihydroquinazolin-4(1H)-ones (11a–j) were evaluated for their in vivo acute toxicity on the gill and liver tissues of fish species Labeo rohita. The results of histo-toxicological study revealed that 2,3-dihydroquinazolin-4(1H)-ones (11a–j) are non-toxic to fish at a rate of 10 µg/L demonstrating their potential application in the field medicinal chemistry. The molecular descriptors and drug-like properties of 2,3-dihydroquinazolin-4(1H)-ones were also analysed.

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新型纤维素负载Bronsted酸性离子液体催化2,3-二氢喹唑啉-4(1H)-酮的绿色合成及组织毒理学研究

本研究强调了利用新型纤维素支撑的Bronsted酸性离子液体[Cell-Al2O3-Pr-Imi-Bu-SO3H]Cl(7)高效合成具有生物活性的2,3-二氢喹唑啉-4(1H)- 1的绿色合成方案。采用FT-IR、TGA、DTG、EDX分析和EDX作图、BET、粉末XRD和FE-SEM等技术对催化剂进行了表征。并以乙醇为绿色溶剂，通过异戊酸酐、芳醛和乙酸铵的一锅三组分缩合反应合成了2,3-二氢喹唑啉-4(1H)- 1。研究了合成的2,3-二氢喹唑啉-4(1H)- 1 （11a-j）对鱼鳃和肝组织的体内急性毒性。组织毒理学研究结果表明，2,3-二氢喹唑啉-4(1H)-ones （11a-j）在10 μ g/L的剂量下对鱼类无毒，显示了其在药物化学领域的潜在应用前景。分析了2,3-二氢喹唑啉-4(1H)- 1的分子描述符和类药物性质。

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来源期刊

Journal of Molecular Liquids 化学-物理：原子、分子和化学物理

CiteScore

10.30

自引率

16.70%

发文量

2597

审稿时长

78 days

期刊介绍： The journal includes papers in the following areas: – Simple organic liquids and mixtures – Ionic liquids – Surfactant solutions (including micelles and vesicles) and liquid interfaces – Colloidal solutions and nanoparticles – Thermotropic and lyotropic liquid crystals – Ferrofluids – Water, aqueous solutions and other hydrogen-bonded liquids – Lubricants, polymer solutions and melts – Molten metals and salts – Phase transitions and critical phenomena in liquids and confined fluids – Self assembly in complex liquids.– Biomolecules in solution The emphasis is on the molecular (or microscopic) understanding of particular liquids or liquid systems, especially concerning structure, dynamics and intermolecular forces. The experimental techniques used may include: – Conventional spectroscopy (mid-IR and far-IR, Raman, NMR, etc.) – Non-linear optics and time resolved spectroscopy (psec, fsec, asec, ISRS, etc.) – Light scattering (Rayleigh, Brillouin, PCS, etc.) – Dielectric relaxation – X-ray and neutron scattering and diffraction. Experimental studies, computer simulations (MD or MC) and analytical theory will be considered for publication; papers just reporting experimental results that do not contribute to the understanding of the fundamentals of molecular and ionic liquids will not be accepted. Only papers of a non-routine nature and advancing the field will be considered for publication.