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)
Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones
Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth
, (2021/12/02)
American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.
Designing of luminescent complexes of europium(III) ion with hydroxyl ketone and nitrogen donor secondary ligands for improving the luminescence performance and biological actions
Hooda, Pooja,Khanagwal, Jyoti,Khatkar, S. P.,Kumar, Rajesh,Poonam,Taxak, V. B.
, (2021/06/17)
Europium based five luminescent europium(III) complexes with 2-hydroxy-4-ethoxyacetophenone (main ligand) and second chromophores, bathophenanthroline, 5,6-dimethyl-1,10-phenanthroline, 1,10-phenanthroline and 2,2-bipyridyl have been prepared by employing cost-effective solution precipitation method. The various advanced techniques are employed to investigate the structural information. Thermal study proclaims the thermal stability of complexes up to 155 °C. The analyzed band-gap for complexes opens the application of these complexes in laser system. The photoluminescent properties of complexes under ultraviolet light clearly reveal the presence of prominent emission peak (5D0→7F2 transition) centered at 611 nm responsible for intense red emission of complexes, which highlights the applicability of these complexes in advanced optoelectronic devices. Judd-Ofelt intensity parameters, internal quantum efficiency and sensitization mechanism confirm the luminescence efficiency of complexes. The complexes display the excellent antimicrobial and antioxidant features.
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.