[C6(MIm)2]2W10O32. 2H2O: A novel and powerful catalyst for the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones under ultrasonic condition

Rostami, Mahboubeh; Khosropour, Ahmad Reza; Mirkhani, Valiollah; Mohammadpoor‐Baltork, Iraj; Tangestaninejad, Shahram

doi:10.1016/j.crci.2011.02.003

Cited by 22 publications

(5 citation statements)

References 35 publications

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“…The oxazolone ring plays an important role in drug discovery strategies. This ring, as a synthon, participates in the synthesis of a wide range of heterocycles and chemical compounds with biological properties ( 13 ). These compounds, with their good stability, are very valuable synthetic intermediates that allow them to be separated and subjected to more sequential reactions ( 21 ).…”

Section: Discussionmentioning

confidence: 99%

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Some novel hybrid quinazoline-based heterocycles as potent cytotoxic agents

et al. 2022

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Background and purpose: In this study, some new cytotoxic hybrid structures were synthesized by combining pyrazolinone and imidazolinone rings with quinazoline pharmacophores. Experimental approach: The benzoxazinone, pyrazolo-quinazoline fused ring, and imidazolinone anchored quinazoline derivatives were synthesized by simple ring-opening, ring expansion, and ring closure strategies from oxazolones. The molecular docking studies of the final derivatives were accomplished on the epidermal growth factor receptor enzyme. The cytotoxic effect of the final compounds on the MCF-7 cell line was evaluated by MTT assay. Findings/Results: The docking results confirmed the optimized electrostatic, H-bonding, and hydrophobic interactions of structures with the key residues of the active site (ΔG bin < -9Kcal/mol). The derivatives have been obtained in good yield and purity, and their structures were confirmed by different methods (FT-IR, 1 H-NMR, 13 C-NMR, and CHNS analysis). The IC 50 s of all final derivatives against the MCF-7 cell line were lower than 10 μM, and between all, the IXa from pyrazolo-quinazolinone class (IC 50 : 6.43 μM) with chlorine substitute was the most potent. Furthermore, all derivatives showed negligible cytotoxicity on HUVEC normal cell line which would be a great achievement for a novel cytotoxic agent. Conclusion and implications: Based on the obtained results, pyrazolo[1,5-c] quinazolin-2-one series were more cytotoxic than imidazolinone methyl quinazoline-4(3H)-ones against MCF-7 cells. Chlorine substitute in the para position of the aromatic ring improved the cytotoxicity effect in both classes. It could be related to the polarizability of a chlorine atom and making better intermolecular interactions. Further pre-clinical evaluations are required for the promising synthesized cytotoxic compounds.

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Section: Discussionmentioning

confidence: 99%

“…The obtained product was recrystallized from ethyl acetate to yield Va (85%) as pale-yellow solid or Vb (91%) as deep-yellow solid. The obtained product was identified by 1 HNMR, FT-IR spectra, and melting point ( 13 ).…”

Section: Methodsmentioning

confidence: 99%

Some novel hybrid quinazoline-based heterocycles as potent cytotoxic agents

et al. 2022

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“…A simple, efficient and environmentally benign approach was designed by Rostami et al . (Scheme ) for the synthesis of 4‐arylidene‐2‐phenyl‐5(4)‐oxazolones ( 77 ) via the Erlenmeyer synthesis of aromatic aldehydes ( 7 ), hippuric acid ( 76 ) and acetic anhydride ( 35 ) in the presence of catalytic amount of di[1, 6‐bis(3‐methylimidazolium‐1‐yl)hexane] decatungstate dihydrate ([C 6 (MIm) 2 ] 2 W 10 O 32 . 2H 2 O) as a new heterogeneous polyoxometalate‐based dicationic ionic liquid under ultrasonic irradiation at room temperature.…”

Section: Ultrasound‐assisted Heterocycles Synthesis In Ionic Liquidsmentioning

confidence: 99%

Ultrasound and Ionic Liquid: An Ideal Combination for Organic Transformations

Kaur¹,

Sharma²,

Banerjee³

2018

ChemistrySelect

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Combination of ultrasound and suitable ionic liquid is a powerful tool to carry out diverse organic transformations. In many occasions, this fruitful combination helps to get the desire products without using any further catalysts even at room temperature. Recyclability of ionic liquid makes a protocol cost effective also. The present review deals with the ultrasound‐assisted organic synthesis in various ionic liquids either as catalyst or reaction media.

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“…[2][3][4][5][6][7][8][9][10][11] However, the inherent defects of DT in structural stability, visible light harvesting, and excitation efficiency hamper its extensive application in organic synthesis as a visible light catalyst. Some efficient strategies have been developed to improve the DT-based photo-catalysis systems, including the use of Fe(III) porphyrins as co-catalysts [12] the use of g-C 3 N 4 /rGO [13] and C 6 (MIm) 2 2 + counter cation [14] to improve the visible absorption and structural stability of DT, respectively. Recently, our research groups have developed simple and efficient modifications or hybridizing engineering (HE) strategies to enhance the visible-light-catalytic performance of DT in the O 2 -based selective oxidations, including the use of acidic additives, [15] C 1 -C 4 alkyl quaternary ammonium cations, [16] CQDs [17] and transition metal ions [18] dopants to overcome the above defects of DT and fine-regulate the synthetic quality, redox ability and photo-physiochemical properties of DT at the molecular level.…”

Section: Introductionmentioning

confidence: 99%

Molybdenum Isomorphously Substituted Decatungstates as Robust and Renewable Photocatalysts for Visible Light‐Driven Oxidation of Hydrocarbons by Molecular Oxygen

et al. 2021

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This article reveals that molybdenum (Mo) heteroatoms isomorphously substituted decatungstates (Mo-DTs) can be conveniently synthesized via copolymerization of tungstate and molybdate in acidic solution. A series of characterizations support that the incorporated Mo heteroatoms play crucial roles in improving the redox capacity and visible light harvesting efficiency of Mo-DTs, especially the photo-excited probability and lifetimes, so that the novel Mo-DTs exhibit a remarkably enhanced photo-catalytic efficiency in the visiblelight-triggered selective oxidation of inert hydrocarbons by O 2 under mild conditions. In the photo-oxidation of cyclohexane under continuous visible light irradiation for 30 h, the best 1 % Mo-DT can achieve 44.8 % conversion and 89.7 % cyclohexanone selectivity in the presence of 2 M HCl, and the regenerated catalyst after simple hydrothermal treatment has excellent reusability. This is the first successful example of incorporating Mo atoms into the skeleton of non-lacunary DTs, which has special significance for expanding the application of DTs in visible-light-catalysis.

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[C6(MIm)2]2W10O32. 2H2O: A novel and powerful catalyst for the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones under ultrasonic condition

Cited by 22 publications

References 35 publications

Some novel hybrid quinazoline-based heterocycles as potent cytotoxic agents

Some novel hybrid quinazoline-based heterocycles as potent cytotoxic agents

Ultrasound and Ionic Liquid: An Ideal Combination for Organic Transformations

Molybdenum Isomorphously Substituted Decatungstates as Robust and Renewable Photocatalysts for Visible Light‐Driven Oxidation of Hydrocarbons by Molecular Oxygen

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