89-84-9Relevant articles and documents
Anticancer activity of some newly synthesized pyrano[2,3-d][1,2,3]triazine derivatives using 1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone as synthon
Ouf, Nabil H.,Amr, Abd El-Galil E.,Sakran, Mohamed I.
, p. 1514 - 1526 (2015)
A series of the newly substituted pyrano[1,2,3]triazine derivatives 3-14 were synthesized using compounds 1 and 2 as starting materials. Compound 2 was methylated using methyl iodide to compound 3, which was treated with aromatic aldehydes to give acryloyl derivatives 4a-c. Compounds 4a,b were reacted with ethyl cyano-acetate to give pyran-3-carboxylates 5a,b which were reacted with ethyl glycinate hydrochloride to give 6a,b. Treatment of 6a,b with hydrazine hydrate gives acid hydrazides 7a,b, which were reacted with 5,5-dimethyl-1,3-cyclohexanedione to give acetohydrazides 8a,b. Cyclization of 8b with 2-(4-nitrobenzylidene)malononitrile afforded hexahydroquinoline 9. However, the acridindione 10 was synthesized by heating of 8b with 2-(4-nitrobenzylidene)malononitrile in acetic acid containing few drops of triethylamine. Treatment of 7a,b with phenyl isothiocyanate or 2,5-hexanedione or phthalic anhydride gave compounds 11a,b, 13a,b and 14a,b, respectively. In the present work, all the selected pyrano[1,2,3]trizine derivatives were soluble in DMSO at concentrations high enough to allow cell experiments, and the in vitro biological activity of these compounds was evaluated by their growth inhibitory potency in liver HEPG2 cancer cell lines. The cytotoxic potency of compounds 3-14 was studied in comparison to the known anticancer drugs 5-fluorouracil and doxorubicin.
Loewe
, p. 931,934 (1977)
Photoluminescence performance of green light emitting terbium (III) complexes with β-hydroxy ketone and nitrogen donor ancillary ligands
Khanagwal, Jyoti,Kumar, Rajesh,Devi, Rekha,Bala, Manju,Sehrawat, Priyanka,Khatkar,Taxak
, p. 742 - 754 (2021/01/18)
An efficient and cost-effective technique, solution precipitation approach is adopted to synthesize five bright green luminescent terbium (III) complexes by employing the main β-hydroxy ketone ligand, 2-hydroxy-4-ethoxyacetophenone, and ancillary ligands like bathophenanthroline, 5,6-dimethyl-1,10-phenanthroline, 1,10-phenanthroline, and 2,2-bipyridyl. The elemental compositions and binding mode of ligand to terbium (III) ion can be validated by using energy dispersive X-ray analysis, elemental analysis, Fourier transform infrared, and proton nuclear magnetic resonance spectroscopy. The complexes are thermally stable up to 158°C and possess the cubic shaped particles as confirmed by thermogravimetric analysis and scanning electron microscopic study, respectively. The band-gap energy (3.02–2.92 eV) of complexes is reckoned through diffuse reflectance spectra, which tailors them as potential candidates in the field of military radars. The photoluminescence studies unveil that the complexes exhibit the bright green luminescence corresponding to 5D4 → 7F5 transition of Tb3+ ion (548 nm) under the excitation wavelength of 395 or 397 nm. The Commission International de I’Eclairage chromaticity coordinates (x, y) and color purity substantiates the green emission of complexes. The energy transfer mechanism elucidates that the main ligand and ancillary ligands sensitize Tb3+ ion, which in turn enhances the luminescence efficiency of the emissive layer of white organic light emitting diodes. The results reveal that the complexes are considered as good contenders in the field of display devices and laser technology. Lastly, in vitro antimicrobial and antioxidant activity proclaim the potent antimicrobial and antioxidant actions of complexes via tube dilution and 2, 2-diphenyl-1-picrylhydrazyl assays, respectively.
EGFR/VEGFR-2 dual inhibitor and apoptotic inducer: Design, synthesis, anticancer activity and docking study of new 2-thioxoimidazolidin-4one derivatives
Mourad, Ahmed A.E.,Farouk,El-Sayed, El-Sherbiny H.,Mahdy, Ahmed R.E.
, (2021/04/23)
Aims: EGFR and VEGFR-2 have emerged as promising targets for cancer management as they play a crucial role in tumor growth, angiogenesis and metastasis. A novel series of 2-thioxoimidazolidin-4-one derivatives were synthesized and evaluated as apoptotic inducers and EGFR/VEGFR-2 dual inhibitors. Main methods: The cytotoxic activities of all synthesized compounds were tested against MCF-7, HepG2 and A549 cell lines. The molecular mechanism of the most promising cytotoxic compounds was investigated via a series of assays including in vitro EGFR and VEGFR-2 inhibitory activity in MCF-7 cell line. Additionally, levels of p53, Bax, Bcl-2, caspase 7, 9 as well as cell cycle analysis were assessed in MCF-7 cell line to gain better understanding of their apoptotic activity. Molecular docking study was carried out to predict binding pattern of these compounds with EGFR and VEGFR-2 active sites. Finally, in silico ADME and drug-likeness profiling were calculated. Key findings: Compounds 6 and 8a exhibited superior cytotoxic activity compared to sorafenib and erlotinib, against the three tested cell lines. In the same context, 6 and 8a showed better EGFR and VEGFR-2 inhibitory activity compared to the reference compounds. The later effect was further supported by the docking study. Furthermore, these compounds displayed potent apoptotic activity as evident by cell accumulation at pre-G1 phase and cell cycle arrest at G2/M phase together with increased p53, caspae-7 and caspase-9 levels and Bax/Bcl-2 ratio. Finally, synthesized compounds have acceptable drug likeness. Significance: Compounds 6 and 8a act as potent dual EGFR/VEGFR-2 inhibitors with evident apoptotic activity.