Design, synthesis and biological evaluation of novel 6-(trifluoromethyl)-N-(4-oxothiazolidin-3-yl)quinazoline-2-carboxamide derivatives as a potential DprE1 inhibitors

Gawad, Jineetkumar; Bonde, Chandrakant

doi:10.1016/j.molstruc.2020.128394

Cited by 12 publications

(5 citation statements)

References 22 publications

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“…Bond vibrations in the range of 1550–1500 cm −1 can be caused by nitro groups [ 47 ]. O- H bond vibrations between 1350 and 1260 cm −1 indicate the presence of phenols and alcohols [ 48 , 49 ].…”

Section: Resultsmentioning

confidence: 99%

Catalytic pyrolysis of olive oil residue to produce synthesis gas: the effect of bulk and nano metal oxides

KARADAĞ¹,

BİLGE²,

DONAR³

et al. 2022

Turkish Journal of Chemistry

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In this study, olive oil residue (OR) biomass was pyrolyzed in the presence of bulk MgO (B-MgO), nano-MgO (N-MgO), bulk ZnO (B-ZnO)), and nano-ZnO (N- ZnO) metal oxides at different temperatures (400, 600, and 800 ºC). Significant results were obtained in terms of synthesis gas formation and CO 2 reduction. The efficiency distribution of the products obtained as a result of the metal oxide-based pyrolysis process and the effects of metal oxides were examined in detail. Nanometal oxides were synthesized by the hydrothermal method. Characterization of metal oxides was carried out by Brunauer–Emmett–Teller (BET), x-ray powder diffraction (XRD) analysis and scanning-electron microscopy-energy dispersive x-ray (SEM-EDX) techniques. The metal concentration of OR biomass was detected via the x-ray fluorescence (XRF) technique. Tar product properties were evaluated by gas chromatography-mass spectrometry (GC-MS) and Fourier transform-infrared spectroscopy (FT-IR) analyzes. Analysis results show that pyrolytic tar is very similar to diesel and gasoline as it contains significant concentrations of aliphatic and aromatic hydrocarbons in composition. In addition, the composition of noncondensable gaseous products was determined by micro gas chromatography (micro-GC) analysis.

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Section: Resultsmentioning

confidence: 99%

Catalytic pyrolysis of olive oil residue to produce synthesis gas: the effect of bulk and nano metal oxides

KARADAĞ¹,

BİLGE²,

DONAR³

et al. 2022

Turkish Journal of Chemistry

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“…1.12 (ii) 11.6 ± 1.3 [59] 3 μg/mL, respectively. 6-(trifluoromethyl)-N-(4-oxothiazolidin-3-yl)quinazoline-2-carboxamide derivatives (Table 5, Compound 2) have been designed as an antitubercular agent for the inhibition of DprE1 [59].…”

Section: Quinazoline As Anti-oxidant Activitymentioning

confidence: 92%

“…μg/mL, respectively. 6-(trifluoromethyl)-N-(4-oxothiazolidin-3-yl)quinazoline-2-carboxamide derivative (Table 5, Compound 2) have been designed as an antitubercular agent for the inhibitio of DprE1 [59]. Compounds with nitro and hydroxyl groups have maximum antitubercula activity against Mycobacterium tuberculosis H37RV.…”

Section: Quinazoline As Anti-tubercular Activitymentioning

confidence: 99%

“…These compounds were tested for their biological activity as anti-oxidant by using three different assays. The results showed that benzotriazoloquinazoline derivative 6-(trifluoromethyl)-N-(4-oxothiazolidin-3-yl)quinazoline-2-carboxamide derivatives (Table 5, Compound 2) have been designed as an antitubercular agent for the inhibition of DprE1 [59]. Compounds with nitro and hydroxyl groups have maximum antitubercular activity against Mycobacterium tuberculosis H37RV.…”

Section: Quinazoline As Anti-oxidant Activitymentioning

confidence: 99%

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Recent Advances on Quinazoline Derivatives: A Potential Bioactive Scaffold in Medicinal Chemistry

et al. 2021

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This paper intended to explore and discover recent therapeutic agents in the area of medicinal chemistry for the treatment of various diseases. Heterocyclic compounds represent an important group of biologically active compounds. In the last few years, heterocyclic compounds having quinazoline moiety have drawn immense attention owing to their significant biological activities. A diverse range of molecules having quinazoline moiety are reported to show a broad range of medicinal activities like antifungal, antiviral, antidiabetic, anticancer, anti-inflammatory, antibacterial, antioxidant and other activities. This study accelerates the designing process to generate a greater number of biologically active candidates.

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“…Quinazolines have a broad range of pharmacological applications, in addition to their low toxicity profiles [ 3 ]. Quinazoline frameworks have great pharmacological activities as antioxidant [ 7 , 8 , 9 ], antidiabetic [ 10 , 11 , 12 ], antibacterial [ 13 , 14 , 15 ], antiviral [ 16 , 17 , 18 ], antimicrobial [ 19 , 20 , 21 ], anticancer [ 22 , 23 ], antihistaminic [ 24 , 25 , 26 ], antidiuretic [ 27 , 28 ], antitubercular [ 29 , 30 , 31 ], and anti-inflammatory [ 32 , 33 , 34 ] agents. Quinazolinones are a type of quinazoline derivative that are biologically active in the same way as quinazoline [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

et al. 2022

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The reaction of 4-hydroxyquinazoline (4HQZ) with aqueous solution of nitric acid afforded the corresponding quinazolinone-nitrate (4HQZN) complex in very good yield. The crystal structure of 4HQZN was determined and its structural and supramolecular structural aspects were analyzed. 4HQZN crystallized in the space group P21/c and monoclinic crystal system with one [4HQZ-H]+[NO3]− formula and Z = 4. Its supramolecular structure could be described as a 2D infinite layers in which the 4HQZN molecules are connected via N-H…O and C-H…O hydrogen bridges. Using DFT calculations, the relative stability of five suggested isomers of 4HQZN were predicted. It was found that the medium effects have strong impact not only on the isomers’ stability but also on the structure of the 4HQZN. It was found that the structure of 4HQZN in DMSO and methanol matched well with the reported X-ray structure which shed the light on the importance of the intermolecular interactions on the isomers’ stability. The structure of 4HQZN could be described as a proton transfer complex in which the nitrate anion acting as an e-donor whiles the protonated 4HQZ is an e-acceptor. In contrast, the structure of the isolated 4HQZN in gas phase and in cyclohexane could be described as a 4HQZ…HNO3 hydrogen bonded complex. Biological screening of the antioxidant, anticancer and antimicrobial activities of 4HQZ and 4HQZN was presented and compared. It was found that, 4HQZN has higher antioxidant activity (IC50 = 36.59 ± 1.23 µg/mL) than 4HQZ. Both of 4HQZ and 4HQZN showed cell growth inhibition against breast (MCF-7) and lung (A-549) carcinoma cell lines with different extents. The 4HQZ has better activity with IC50 of 178.08 ± 6.24 µg/mL and 119.84 ± 4.98 µg/mL, respectively. The corresponding values for 4HQZN are 249.87 ± 9.71 µg/mL and 237.02 ± 8.64 µg/mL, respectively. Also, the antibacterial and antifungal activities of 4HQZN are higher than 4HQZ against all studied microbes. The most promising result is for 4HQZN against A. fumigatus (MIC = 312.5 mg/mL).

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Design, synthesis and biological evaluation of novel 6-(trifluoromethyl)-N-(4-oxothiazolidin-3-yl)quinazoline-2-carboxamide derivatives as a potential DprE1 inhibitors

Cited by 12 publications

References 22 publications

Catalytic pyrolysis of olive oil residue to produce synthesis gas: the effect of bulk and nano metal oxides

Catalytic pyrolysis of olive oil residue to produce synthesis gas: the effect of bulk and nano metal oxides

Recent Advances on Quinazoline Derivatives: A Potential Bioactive Scaffold in Medicinal Chemistry

Synthesis, X-ray Structure, Hirshfeld, DFT and Biological Studies on a Quinazolinone-Nitrate Complex

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