Synthesis and antimicrobial activity of novel quinazolinone–thiazolidine–quinoline compounds

Desai, N. C.; Dodiya, Amit M.; Shihory, Niraj

doi:10.1016/j.jscs.2011.04.001

Cited by 38 publications

(16 citation statements)

References 28 publications

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“…anticancer, antibacterial, anticonvulsant, anti-inflammatory, antiulcer and analgesic [1][2][3]. The quinazolines derivatives have been synthesized and characterized as active candidates [4].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activities, DFT and QSAR studies of quinazolinone compounds

Al‐Sehemi¹,

Irfan²,

Alrumman³

et al. 2016

Bull. Chem. Soc. Eth.

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ABSTRACT. The quinazolinone compounds (1 and 2) in this work were examined for their in vitro antibacterial activities against gram-positive (Staphylococcus aureus) and gram-negative bacteria (Klebsiella pneumonia, Proteus bacilli and Shigella flexneri). Compared to the reference antibiotic chloramphenicol, these compounds showed high antibacterial activities against studied strains with inhibition zones observation. The ground state geometries have been optimized by using density functional theory (DFT) at B3LYP/6-31G* level of theory. The absorption spectra have been calculated by using time dependent density functional theory (TDDFT) with and without solvent. The effect of different functionals (B3LYP, MPW1PW91, and PBE1PBE) on the absorption wavelengths has been studied. The ionization potential (IP), electron affinity (EA), energy gap (Egap), electronegativity (χ), hardness (η), electrophilicity (ω), softness (S) and electrophilicity index (ωi) were computed and discussed. The nonlinear optical (NLO) properties vary by changing the theory (DFT to HF) or functional (B3LYP to CAM-B3LYP). The physicochemical parameters have been studied by quantitative structure-activity relationship (QSAR). The computed properties of investigated compounds have been compared with the Chloramphenicol as well as available experimental data.

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Section: Introductionmentioning

confidence: 99%

Antibacterial activities, DFT and QSAR studies of quinazolinone compounds

Al‐Sehemi¹,

Irfan²,

Alrumman³

et al. 2016

Bull. Chem. Soc. Eth.

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“…Generally, benzylaminoethanol (10 mmol, 1.4 mL) was added dropwise into a solution of potassium hydroxide (50 mmol, 2.81 mg) in ethanol (50 mL 13 C NMR (400 MHz, CD 3 CN, δ ppm): 196.9 (C S); 135-127 (4C, C-Ar); 56.3 (C-N); 51.9 (C-N); and 26.8 (C-S).…”

Section: Synthesis Of 3-benzyl-13-thiazolidine-2-thionementioning

confidence: 99%

“…e FTIR and 1 H NMR data strongly suggested the coordination between the thiazolidine ligand and silver centre via the thione sulfur. In the 13 C NMR spectrum, the proof of the bonding between the aforementioned molecules was also reflected by the C�S signal, in which a change in the chemical shift value (ca. δ 0.2 ppm) was present; again, this was not seen as in free thiazolidine ligands [33].…”

Section: Spectroscopicdataanalysismentioning

confidence: 99%

“…Numerous ligands derived from mono-and diphosphines have been explored for their ability to coordinate with silver, hence enabling their development as antiproliferative agents [11]. iazolidine is one of the compounds which show good potential in various biological activities [12,13]. Based on the analyses and databases from the National Cancer Institute (NCI, USA), approximately about 42,247 compounds which consist of 734 nonfused and 146 fused thiazolidine derivatives are active in three tumor cell line assays.…”

Section: Introductionmentioning

confidence: 99%

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New Silver Complexes with Mixed Thiazolidine and Phosphine Ligands as Highly Potent Antimalarial and Anticancer Agents

Sofyan

Nordin

Razak

et al. 2018

Journal of Chemistry

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Five silver(I) complexes containing a mixed ligand system of phosphine and thiazolidine were successfully synthesized. e structural information of the complexes was assembled using various spectroscopic techniques such as CHN elemental analysis, Fourier transformed infrared (FTIR), 1 H, 13 C, and 31 P{ 1 H} NMR spectroscopy, and thermogravimetric analysis (TGA). A bidentate phosphine ligand acted as a chelating agent which bond to the silver in 1 : 2 molar ratios. Meanwhile, thiazolidine was attached to the silver in a 1 : 1 molar ratio. e antiplasmodial properties of all synthesized complexes were investigated on chloroquine-resistant P. falciparum parasite via HRP2 assays and cytotoxicity tests on Vero cells. Of all the synthesized complexes, complex 2 showed the highest SI value (more than 12.4) followed by complex 5 (6.6). e potent properties of compounds 2 and 5 were also noted in the in vitro antiproliferative assays involving MDA-MB-231 and MCF-7 breast cancer cell lines as well as HT-29 colon cancer cell line. Complex 2 was selective for MDA-MB-231 cells (GI 50 � 1.9 ± 0.3 µM), while complex 5 acted predominantly on breast carcinoma cells (GI 50 MDA-MB-231 � 4.7 ± 1.1 µM; MCF-7 � 2.9 ± 0.9 µM) instead of colon carcinoma (HT-29) cells (GI 50 � 15.1 ± 1.9 µM).

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“…Quinazolinones and their fused derivatives are scaffolds for wide range of biological activities. Altering substituents as well as their position on the ring had a great influence on the activity [1]quinazolinones were reported to act as anti-inflammatory, [2][3][4][5]anti-ulcerative, [6] antifungal, [7,8]anticancer, [9][10][11]anti-tuberculosis, [12]anticonvulsant, [13]antimicrobial, [14][15][16]antibacterial, [17][18][19]antiviral, [20]antiparkinsonian, [21]antihypertensive, [5,22,23] antidepressant, [24] anti-malarial, [25]antirheumatic, [26]and anti HIV [27]. Ultrasound provides exceptional conditions of elevated temperature and pressure that is superior to traditional chemistry in yields and reaction times.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

et al. 2019

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P HOSPHODIESTERASE 7A enzyme is one of the most recent targets for designing potent anti-inflammatory agents with minimal side effects. Quinazolinones are unique building blocks of wide biological activities. Different quinazolinones were reported to act as Phosphodiesterase 7A inhibitors anti-inflammatory particularly against chronic inflammation and autoimmune disease. Ultrasound is a green convenient method for synthesis of different heterocyclic ring system that is advantageous in terms of yield and reaction time. Ultrasound was used for one pot synthesis of 3-substituted 6-aryldihydroisoindolo[2,1-a] quinazolin-5,11diones and 3-arylquinazolin-2,4(1H,3H)-diones. Seventeen compounds were synthesized in good yields. The synthesized compounds were inspected for in vitro inhibitory activity against phosphodiesterase7A enzyme. Molecular docking was used to study the mode of interaction of all the synthesized compounds into the enzyme phosphodiesterase 7A binding site. Five compounds showed high inhibitory activity of enzyme Phosphodiesterase 7A at micro-molar level compared to reference drug. The compounds showed good recognition at the enzyme binding site in the molecular docking. There was a good agreement between the molecular docking and the biological screening results.

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Synthesis and antimicrobial activity of novel quinazolinone–thiazolidine–quinoline compounds

Cited by 38 publications

References 28 publications

Antibacterial activities, DFT and QSAR studies of quinazolinone compounds

Antibacterial activities, DFT and QSAR studies of quinazolinone compounds

New Silver Complexes with Mixed Thiazolidine and Phosphine Ligands as Highly Potent Antimalarial and Anticancer Agents

Ultrasound one pot synthesis of fused quinazolinones and quinazolinediones, screening and molecular docking study as phosphodiesterase 7A inhibitors.

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