2770-89-0Relevant articles and documents
Synthesis, biological evaluation, and: In silico studies of novel chalcone: In pyrazoline-based 1,3,5-triazines as potential anticancer agents
Abonia, Rodrigo,Insuasty, Braulio,Insuasty, Henry,Lauria, Antonino,Martorana, Annamaria,Moreno, Leydi M.,Quiroga, Jairo
, p. 34114 - 34129 (2020)
A novel series of triazin-chalcones (7,8)a-g and triazin-N-(3,5-dichlorophenyl)pyrazolines (9,10)a-g were synthesized and evaluated for their anticancer activity against nine different cancer strains. Triazine ketones 5 and 6 were synthesized from the cyanuric chloride 1 by using stepwise nucleophilic substitution of the chlorine atom. These ketones were subsequently subjected to a Claisen-Schmidt condensation reaction with aromatic aldehydes affording chalcones (7,8)a-g. Then, N-(3,5-dichlorophenyl)pyrazolines (9,10)a-g were obtained by cyclocondensation reactions of the respective chalcones (7,8)a-g with 3,5-dichlorophenylhydrazine. Among all the evaluated compounds, chalcones 7d,g and 8g exhibited more potent in vitro anticancer activity, with outstanding GI50 values ranging from 0.422 to 14.9 μM and LC50 values ranging from 5.08 μM to >100 μM. In silico studies, for both ligand- and structure-based, were executed to explore the inhibitory nature of chalcones and triazine derivatives. The results suggested that the evaluated compounds could act as modulators of the human thymidylate synthase enzyme. This journal is
New chalcone-tethered 1,3,5-triazines potentiate the anticancer effect of cisplatin against human lung adenocarcinoma A549 cells by enhancing DNA damage and cell apoptosis
El-Wakil, Marwa H.,Khattab, Sherine N.,El-Yazbi, Amira F.,El-Nikhely, Nefertiti,Soffar, Ahmed,Khalil, Hosam H.
, (2020)
In the pursuit of new compounds for co-treatment to enhance the anticancer efficacy of cisplatin against lung adenocarcinoma, a series of chalcone-tethered 1,3,5-triazines was designed and synthesized. MTT assay was used to evaluate the anticancer activity of the combinations in which two hybrids 10 and 12 were found to significantly inhibit A549 cancer cells viability and their IC50 values were 24.5 and 17 μM, respectively in reference to cisplatin (IC50 = 21.5 μM). The combined effect of cisplatin with each of 10 and 12 was analyzed according to Chou-Talalay method against both A549 and normal human fibroblast cells. Mechanistic studies employing MALDI-TOF MS and fluorescence spectroscopy using Evagreen probe inferred that 10 and 12 induced DNA double strand breaks in contrast to cisplatin which induces DNA interstrand cross-links. Also, DNA damage kinetics study demonstrated the difference in the rate of DNA damage induced by both 10 and 12 alone and in combination with cisplatin. Further Annexin V-FITC/propidium iodide dual staining assay provided evidence that 10 and 12 induced apoptosis via different pattern to cisplatin and their combination with cisplatin promoted more cells to enter late apoptosis and necrosis. Molecular docking of 10 and 12 in the active pocket of DNA dodecamer displayed their binding modes with higher number of stable hydrogen bond donor as well as π-H interactions in reference to the original ligand.
Synthesis of new 1,3,5-triazine-based 2-pyrazolines as potential anticancer agents
Moreno, Leydi M.,Quiroga, Jairo,Abonia, Rodrigo,Ramírez-Prada, Jonathan,Insuasty, Braulio
, (2018)
A new series of 1,3,5-triazine-containing 2-pyrazoline derivatives (8–11)a–g was synthesized by cyclocondensation reactions of [(4,6-bis((2-hydroxyethyl)amino)-1,3, 5-triazin-2-yl)amine]chalcones 7a–g with hydrazine hydrate and derivatives. Chalcones 7a–g were obtained by Claisen-Schmidt condensation between aromatic aldehydes and triazinic derivative 5, which was synthesized in high yield by a microwave-assisted reaction. Seventeen of the synthesized compounds were selected and tested by the US National Cancer Institute (NCI) for their anticancer activity against 58 different human tumor cell lines. Compounds 7g and 10d,e,g showed important GI50 values ranging from 0.569 to 16.6 μM and LC50 values ranging from 5.15 to >100 μM.
Synthesis, anti-inflammatory, cyclooxygenases inhibitions assays and histopathological study of poly-substituted 1,3,5-triazines: Confirmation of regiospecific pyrazole cyclization by HMBC
Elshemy, Heba A.H.,Abdelall, Eman K.A.,Azouz, Amany A.,Moawad, Abeer,Ali, Waleed A.M.,Safwat, Nesreen M.
, p. 10 - 21 (2017)
Three novel triazines series were prepared. These series are pyrazolines (4a and 4b), pyrazoles (6a, 6b and 8a-d) and isoxazoles (7a and 7b). Such series were designed as COX-2 inhibitors. All compounds were characterized by using spectroscopic methods and elemental analysis. Regarding COX-2, compounds 5b, 4a and 3b were the most active with IC50in the range of 0.55–0.87?μM. Most of synthesized compounds were relatively more potent to celecoxib (0.78?μM), diclofenac (2.94?μM) and indomethacin (7.24?μM). A molecular modeling study was performed for the most active compounds. Histopathological evaluation also was done to estimate the safety of compounds. Finally, structure elucidation of pyrazole 8 was studied by 2D NMR.
Synthesis and antimicrobial activity of 2-{4′-[(5″-Aryl)- 4″-5″-dihydro-1-phenyl pyrazol-3″-yl]-Phenyl Amino}-6-[BIS (2?-chloro ethyl) aminoj-4- methoxy-1,3,5-triazines
Kathiriya,Patolia,Purohit
, p. 285 - 286 (2013/09/24)
A new series of phenyl pyrazolyltriazines has been prepared and screesned for their antimicrobial activity.
