ChemInform Abstract: Synthesis and Characterization of New Chalcone Derivatives from cis‐Bicyclo[3.2.0]hept‐2‐en‐6‐one.

Ceylan, Mustafa; Fındık, Esra

doi:10.1002/chin.200933096

Cited by 3 publications

(4 citation statements)

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“…The structures of all compounds were elucidated by spectroscopic methods (IR, NMR) together with elemental analysis and comparison with literature data. All physical and spectroscopic data are in accordance with the proposed structures …”

Section: Resultssupporting

confidence: 79%

“…The 7‐benzylidenebicyclo[3.2.0]hept‐2‐en‐6‐ones 3a – 3m were synthesized from the condensation of substituted benzaldehyde derivatives 2a – 2m with (1 R ,5 S )‐bicyclo[3.2.0]hept‐2‐en‐6‐one ( 1 ), which was commercially available in the basic form according to the previously published method . The compounds 3a – 3i are known and the compounds 3j – 3m were synthesized for the first time in this study.…”

Section: Resultsmentioning

confidence: 99%

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Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Ceylan

Erkan

Yağlıoğlu

et al. 2020

Chemistry & Biodiversity

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The 2-[2-(2-phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were synthesized from the reactions of 7benzylidenebicyclo[3.2.0]hept-2-en-6-ones with 2-aminobenzenethiol. The antiproliferative activities of 2-[2-(2phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were determined against C6 (rat brain tumor) and HeLa (human cervical carcinoma cells) cell lines using BrdU cell proliferation ELISA assay. Cisplatin and 5-fluorouracil (5-FU) were used as standards. The most active compound was 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl] cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 cell lines with IC 50 = 5.89 μM value (cisplatin, IC 50 = 14.46 μM and 5-FU, IC 50 = 76.74 μM). Furthermore, the most active compound was 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl) ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa cell lines with IC 50 = 3.98 μM (cisplatin, IC 50 = 37.95 μM and 5-FU, IC 50 = 46.32 μM). Additionally, computational studies of related molecules were performed by using B3LYP/6-31G + (d,p) level in the gas phase. Experimental IR and NMR data were compared with the calculated results and were found to be compatible with each other. Molecular electrostatic potential (MEP) maps of the most active 2-{(1S,2S)-2-[(E)-2-(2methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa and the most active 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 were investigated, aiming to determine the region that the molecule is biologically active. Biological activities of mentioned molecules were investigated with molecular docking analyses. The appropriate target protein (PDB codes: 1 M17 for the HeLa cells and 1JQH for the C6 cells) was used for 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole and 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole molecules exhibiting the highest biological activity against HeLa and C6 cells in the docking studies. As a result, it was determined that these molecules are the best candidates for the anticancer drug. Figure 5. Interaction of molecule 5c (pink balls) with protein 1M17 and that of molecule 5e (red balls) with protein 1JQH.1 H-NMR (400 MHz, CDCl 3 ): 8.02 (d, J = 8.2, 1H), 7.87 (d, J = 7.8, 1H), 7.48 (ddd, J = 8.3, 7.2, 1.3, 2H), 7.43-7.31 (m, 4H), 7.06 -6.97 (m, 2H), 6.46 (d, J = 15.8, 1H), 6.22 (dd, J = 15.8, 8.0, 1H), 5.98 -5.92 (m, 1H), 5.82 -5.76 (m, 1H), 3.99 -3.87 (m, 1H), 3.77 (dt, J = 8.8, 7.3, 1H), 3.16 -3.03 (m, 1H), 3.00 -2.89 (m, 1H). 13 C-NMR (101 MHz,

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Section: Resultssupporting

confidence: 79%

Section: Resultsmentioning

confidence: 99%

Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Ceylan

Erkan

Yağlıoğlu

et al. 2020

Chemistry & Biodiversity

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“…Synthesis of chalcone derivatives. Chalcone derivatives were synthesized based on Claisen-Schmidt condensation as previously reported (12). NaOH was added to a powerfully stirred solution of cis-bicyclo[3.2.0]hept-2-en-6-one (1 in Figure 1) and aldehyde derivatives (2 in Figure 1).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 2-Substituted Benzothiazole Derivatives and Their In Vitro Anticancer Effects and Antioxidant Activities Against Pancreatic Cancer Cells

Üremiş

Uremis

Tolun

et al. 2017

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Pancreatic cancer is one of the deadliest malignancies characterized by strong resistance to almost all chemotherapeutic agents and radiotherapy. In this study, we aimed to investigate the anticancer effect, enzymatic antioxidant activity [superoxide dismutase (SOD), glutathione peroxidase (GPx)] and total antioxidant capacity (TAC) of synthesized benzothiazole compounds against adenocarcinoma cancer cells (PANC-1). 2-((1S,2S)-2-((E)-4-nitrostyryl)cyclopent-3-en-1-yl)benzo[d]thiazole and 2-((1S,2S)-2-((E)-4-fluorostyryl) cyclopent-3-en-1-yl)benzo[d]thiazole containing 2-substituted benzothiazole group were synthesized in two steps. PANC-1 cells were treated with different concentrations of benzothiazole compounds (5, 25, 50. 75 and 100 μM) for 48 h and their cytotoxicity effects were determined by the MTT assay. To determine whether these compounds induced apoptosis, PANC-1 cells were treated with increasing concentrations of the synthetic products. Our study showed that the synthesized compounds have antiproliferative effects against PANC-1 cells and reduced cell viability. These compounds induced apoptosis of pancreatic cancer cells and at the same time reduced the activity of SOD and GPx and reduced TAC. On the basis of these findings, these synthesized benzothiazole compounds may be considered as a potential therapeutic drug against human PANC-1 cancer cells.

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“…The resultant precipitate is poured into ice and filtered, washed with water, dried and recrystallized from ethanol (Figure 2). [23][24][25]…”

Section: Synthesis Of 2-mercapto-4-hydroxy-6-amino Pyrimidine(1)mentioning

confidence: 99%

In-silico Studies, Synthesis and Antioxidant Studies of Different Substituted 7-Phenyl-5-(Thiophen-2-Yl)- 2-Thioxo-2,3-Dihydropyrido[2,3-D]Pyrimidine-4(1h)- Ones

Shetty¹,

Chandana²,

Shastry³

et al. 2022

Ind. J. Pharm. Edu. Res

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Background: Free radicals and ROS which are formed in normal physiological conditions, damages the cells if it is not eliminated by endogenous system which causes oxidative stress. Pyridopyrimidines are important molecule in heterocyclic chemistry, gaining interest because of their biological and pharmacological activities, especially for their potential anti-tumor, antibacterial and tyrosine kinase inhibitors, among other pharmacological properties along with anti-oxidant properties. Materials and Methods: In the current study, novel pyridopyrimidines derivatives i.e different substituted 7-phenyl-5-(thiophen-2-yl)-2-thioxo-2,3-dihydropyrido[2,3-d]pyrimidine-4(1H)-one(3a-p) were synthesized to develop potent anti-oxidant agent. Based the in-silico studies, especially depending on the docking score, 8 compounds were selected for the synthesis and evaluated for their anti-oxidant potency. Selected compounds were synthesized using mercapto-4hydroxy-6-amino pyrimidine (1) and substituted α, βunsaturated ketones(2a-p). Results: Synthesized compounds were characterized by IR, NMR and Mass spectra. In-vitro antioxidant studies were performed for 8 best scored compounds by DPPH assay and nitric oxide inhibition assay. From the in-vitro result, compound 3j, 3a, and 3o are considered as promising molecules. Conclusion: The promising activity may be because of presence of electron releasing group (3a-p-OH, 3o-p-NH 2 ) and electron withdrawing group (3jp-CF 3 ) which can be considered as lead molecules for the further discovery.

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ChemInform Abstract: Synthesis and Characterization of New Chalcone Derivatives from cis‐Bicyclo[3.2.0]hept‐2‐en‐6‐one.

Cited by 3 publications

References 1 publication

Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Synthesis of 2-Substituted Benzothiazole Derivatives and Their In Vitro Anticancer Effects and Antioxidant Activities Against Pancreatic Cancer Cells

In-silico Studies, Synthesis and Antioxidant Studies of Different Substituted 7-Phenyl-5-(Thiophen-2-Yl)- 2-Thioxo-2,3-Dihydropyrido[2,3-D]Pyrimidine-4(1h)- Ones

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