Synthesis and biological evaluation of some new pyrimidines via a novel chalcone series

Trivedi, Anjali; Dodiya, Dipti K.; Ravat, N. R.; Shah, V. H.

doi:10.3998/ark.5550190.0009.b13

Cited by 49 publications

(15 citation statements)

References 4 publications

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“…The synthesis of the target 3-cyano pyridine derivatives is described in Scheme 1. The starting chalcones 3a-3e were prepared in high yields by Claisen-Schmidt condensation [25,26] of 4-fluorobenzyloxyacetophenone with benzaldehyde/substituted benzaldehydes. The structures of these chalcones were confirmed based on their spectral and elemental analysis.…”

Section: Chemistrymentioning

confidence: 99%

Discovery of Novel 3-Cyanopyridines as Survivin Modulators and Apoptosis Inducers

et al. 2020

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The overexpression of survivin is usually accompanied by an increased resistance of cancer cells to chemotherapeutic agents in addition to cancer aggressiveness. Consequently, survivin is considered as an attractive target to develop new promising anticancer candidates. A series of novel 3-cyanopyridine derivatives was synthesized and assessed for their cytotoxic activity against three human cancer cell lines: prostate carcinoma (PC-3), breast cancer (MDA-MB-231) and hepatocellular carcinoma (HepG2). In addition, their activities were evaluated in comparison with a standard anticancer drug 5-FU. Compounds 5c and 5e both exhibited promising cytotoxicity against all the tested cell lines; especially, 5e showed better cytotoxic effect than the reference drug 5-FU. In order to evaluate the safety of these compounds, they were tested on the normal cell line WI-38, revealing their toxic selectivity toward cancer cells over normal ones. Further studies were performed in order to understand their mechanism of action; we examined the ability of our promising compounds 5c and 5e to induce cell cycle arrest. Both resulted in a notable induction of cell cycle arrest at the G2/M phase, along with an increase in the DNA content in the pre-G1 phase, giving us an indication of the incidence of apoptosis. 5c and 5e were further subjected to additional study using Annexin V-FITC assay in order to evaluate their ability to induce apoptosis. The results showed a marked increase in the early and late apoptotic cells, as well as an increase in the percentage of necrosis. Furthermore, Western blotting assay was accomplished using different concentrations of 5c and 5e. The results revealed a striking reduction in survivin expression through proteasome-dependent survivin degradation in addition to a decrease in the expression of some other inhibitor of apoptosis proteins (IAP) family proteins: Livin, XIAP, and C-IAP1 in a concentration-dependent manner. A docking study of 5c and 5e compounds in the dimerization site of survivin was also performed, showing agreement with the in vitro anti-survivin activity.

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Section: Chemistrymentioning

confidence: 99%

Discovery of Novel 3-Cyanopyridines as Survivin Modulators and Apoptosis Inducers

et al. 2020

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“…1,3-Diaryl-2-propene-1-one derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) were prepared according to the procedure described elsewhere in the literature. 53−61 Equimolar quantities of substituted acetophenone (10 mmol) and substituted benzaldehyde (10 mmol) in ethanol (10 mL) were stirred at 0-5 • C for 30 min.…”

Section: General Methods For the Synthesis Of Substituted 13-diaryl-2-propene-1-one (1-19)mentioning

confidence: 99%

Biological evaluation and synthesis of new pyrimidine-2(1H)-ol/-thiol derivatives derived from chalcones using the solid phase microwave method

Fandaklı¹,

Kahriman²,

Yücel³

et al. 2018

Turk J Chem

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Twenty-five new hydroxy-and methoxy-substituted 4,6-diarylpyrimidin-2(1H)-ol (20-34) and 4,6-diarylpyrimidine-2(1H)-thiol derivatives (35-44) were synthesized from the reaction of the corresponding 1,3-diaryl-2-propene-1one compounds (1-19) with urea or thiourea using the solid-phase microwave method. All the new synthetic compounds (20-44) were evaluated with regard to their α-glucosidase activity. However, only compounds 22-25, 27, 31, 34, 35, 37, and 40 exhibited a greater inhibitory effect than standard acarbose. The IC 50 values of the active compounds ranged between 2.36 and 13.34 µ M. The 25 new compounds were also screened for their in vitro pancreatic lipase activity and compounds 20-27 and 35-39 were found to be active. Of these compounds 26, 27, and 39 exhibited the best antilipase activities at concentrations of 0.40 ± 0.06, 0.26 ± 0.07, and 0.29 ± 0.026 µ M. All the new compounds (20-44) were evaluated for their in vitro antimicrobial activity for nine test microorganisms. Compounds 20-24 and 35-39 were determined to possess a significant broad spectrum against the gram-positive bacteria Escherichia faecalis, Staphylococcus aureus, and Bacillus cereus among the tested bacterial agents. Compounds 20-24 and 35-39 exhibit the best activity against Mycobacterium smegmatis, with minimum inhibitory concentrations of 62.5-500 µ g/mL, indicating their potential use as antituberculous agents.

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“…In addition, the signals at 7.282 and 7.436 ppm (Figure 6c) were assigned to the hydrogen signal of -CH in the aromatic compound [37], which shifted to 7.315 and 7.445 ppm after binding with calcium ions. The signals at 3.385, 3.357, and 3.307 ppm were ascribed to methylene in -N-CH 2 (Figure 6d,e) [38][39][40], which changed from three peaks to one peak after binding with Ca(II). The signals at 3.142 and 3.136 ppm were attributed to the hydrogen atom of -O-C-H [41].…”

Section: H Nmr Analysis Of Fns and Fns-ca(ii)mentioning

confidence: 99%

Food-Borne Nanocarriers for Calcium Delivery: A New Choice for Nutrient Supplements

Wang

Chen

Song

et al. 2022

Foods

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Calcium is considered as an important nutrient element for the maintenance of human health, and food-borne nanoparticles (FNs) produced during food processing may have potential as nanocarriers for calcium ion delivery. Beef is an important source of animal protein that has high protein and low fat content and is rich in a variety of amino acids; thus, beef may be a suitable material for the development of calcium nanocarriers. In this paper, FNs were synthesized from beef by one-step hydrothermal synthesis. The FNs had a spherical shape with a size of about 3.0 nm and emitted a bright blue fluorescence under 365 nm ultraviolet irradiation. The amino nitrogen atom and carboxyl oxygen atom of the functional groups on the surface of the FNs were the main binding sites for the chelation of Ca(II). The size of the FNs-Ca(II) complex was about 4.75 nm, and the specific signal peak of calcium at 3.7 keV was observed in its energy dispersive X-ray spectroscopy spectrum. The viability of cells treated with FNs-Ca(II) was more than 65%, while viability was only 60% after treatment with CaCl2. The results showed that the FNs from beef have great potential in calcium delivery for the development of a calcium supplement.

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Synthesis and biological evaluation of some new pyrimidines via a novel chalcone series

Cited by 49 publications

References 4 publications

Discovery of Novel 3-Cyanopyridines as Survivin Modulators and Apoptosis Inducers

Discovery of Novel 3-Cyanopyridines as Survivin Modulators and Apoptosis Inducers

Biological evaluation and synthesis of new pyrimidine-2(1H)-ol/-thiol derivatives derived from chalcones using the solid phase microwave method

Food-Borne Nanocarriers for Calcium Delivery: A New Choice for Nutrient Supplements

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