Synthesis and Cytotoxicity Screening of Piperazine‐1‐carbodithioate Derivatives of 2‐Substituted Quinazolin‐4(3<i>H</i>)‐ones

Cao, Sheng‐Li; Guo, Yanwen; Wang, Xianbo; Zhang, Mei; Ye, Feng; Jiang, Yuyang; Wang, Yue; Gao, Qian; Ren, Jian Wen

doi:10.1002/ardp.200800148

Cited by 13 publications

(4 citation statements)

References 17 publications

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“…(known as 2-amino-5-methylbenzoic acid) and 4-(aminomethyl)benzoic acid (PAMBA) are biologically active molecules serving as pharmaceutical intermediates [1] and their derivatives are considered as potential agents for anti-cancer chemotherapy [2][3][4] and evaluated for their cytotoxic activity [5,6]. Furthermore, PAMBA, described for its antifibrinolytic action [7,8], is known with his derivatives to inhibit the proliferation of endothelial cells [9,10] and are additionally proved to be antiproteolytic [11].…”

Section: -Carboxy-4-methylanilinementioning

confidence: 99%

A Comparative Theoretical and Spectroscopic Study of Aminomethylbenzoic Acid Derivatives as Potential NLO Candidates

Direm

Sayın

2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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Three aminomethylbenzoic acid derivatives were theoretically studied at M062X/6-311++G(d,p) level in a vacuum, namely 2-ammonio-5-methylcarboxybenzene perchlorate (1), 4-(ammoniomethyl) carboxybenzene nitrate (2) and 4-(ammoniomethyl)carboxybenze perchlorate (3). The compounds’ structures were fully optimized and compared with the single-crystal X-ray diffraction results, showing a very close agreement with the experimental structural parameters. Their IR, 1H- and 13C-NMR spectra were calculated and examined in detail. Furthermore, the molecular electrostatic potential (MEP) maps of the studied compounds were investigated and the strength of the non-covalent interactions evaluated. In addition to these results, the NLO properties of the three compounds were predicted.

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Section: -Carboxy-4-methylanilinementioning

confidence: 99%

A Comparative Theoretical and Spectroscopic Study of Aminomethylbenzoic Acid Derivatives as Potential NLO Candidates

Direm

Sayın

2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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“…1) containing (pyridin-3-yl)methylamine moiety inhibited the growth of A549 (human lung cancer), HCT-8 (human colorectal cancer) and Bel-7402 (human liver cancer) cell lines with IC 50 values within micromolar concentrations [15]. For 4 (3H)-quinazolinones bearing other alkyl than methyl, aryl, or heteroaryl group at the C2 position, however, their dithiocarbamate derivatives hardly showed any inhibitory activity against the growth of A549, HCT-8 and Bel-7402 cell lines [16]. Therefore, it seems that a methyl group at the C2 position is crucial for this type of compounds to generate cytotoxic effects.…”

Section: Introductionmentioning

confidence: 95%

Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates

Cao

Wang

Zhu

et al. 2010

European Journal of Medicinal Chemistry

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“…The rise of bacterial resistance to traditional antibiotics has evoked a search for new antimicrobial agents [ 4 ]. A number of quinazolinone derivatives revealed selective cytotoxicity towards specific types of cancer cells [ 17 , 18 , 19 , 20 ] and significant antioxidant properties [ 6 , 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant, Cytotoxic, Genotoxic, and DNA-Protective Potential of 2,3-Substituted Quinazolinones: Structure—Activity Relationship Study

Hricovíniová

Kozics

2021

IJMS

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The evaluation of antioxidant compounds that counteract the mutagenic effects caused by the direct action of reactive oxygen species on DNA molecule is of considerable interest. Therefore, a series of 2,3-substituted quinazolinone derivatives (Q1–Q8) were investigated by different assays, and the relationship between their biological properties and chemical structure was examined. Genotoxicity and the potential DNA-protective effects of Q1–Q8 were evaluated by comet assay and DNA topology assay. Antioxidant activity was examined by DPPH-radical-scavenging, reducing-power, and total antioxidant status (TAS) assays. The cytotoxic effect of compounds was assessed in human renal epithelial cells (TH-1) and renal carcinoma cells (Caki-1) by MTT assay. Analysis of the structure–activity relationship disclosed significant differences in the activity depending on the substitution pattern. Derivatives Q5–Q8, bearing electron-donating moieties, were the most potent members of this series. Compounds were not genotoxic and considerably decreased the levels of DNA lesions induced by oxidants (H2O2, Fe2+ ions). Furthermore, compounds exhibited higher cytotoxicity in Caki-1 compared to that in TH-1 cells. Substantial antioxidant effect and DNA-protectivity along with the absence of genotoxicity suggested that the studied quinazolinones might represent potential model structures for the development of pharmacologically active agents.

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Synthesis and Cytotoxicity Screening of Piperazine‐1‐carbodithioate Derivatives of 2‐Substituted Quinazolin‐4(3H)‐ones

Cited by 13 publications

References 17 publications

A Comparative Theoretical and Spectroscopic Study of Aminomethylbenzoic Acid Derivatives as Potential NLO Candidates

A Comparative Theoretical and Spectroscopic Study of Aminomethylbenzoic Acid Derivatives as Potential NLO Candidates

Synthesis and cytotoxic activity of N-((2-methyl-4(3H)-quinazolinon-6-yl)methyl)dithiocarbamates

Antioxidant, Cytotoxic, Genotoxic, and DNA-Protective Potential of 2,3-Substituted Quinazolinones: Structure—Activity Relationship Study

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