1442115-83-4Relevant academic research and scientific papers
Chemical profiling, cytotoxic activities through apoptosis induction in human fibrosarcoma and carcinoma cells, and molecular docking of some 1,2,3-triazole-isoxazoline hybrids using the eugenol as a precursors
Aatif, Abdeljalil,Ait Itto, My Youssef,Ait Lahcen, Marouane,Bimoussa, Abdoullah,Byadi, Said,Essaber, Mohamed,Morjani, Hamid,Oubella, Ali,Podlipnik, Crtomir,Taia, Abdelmaoujoud
, (2022/02/21)
In this research paper, we report the cytotoxic and apoptotic effects of 1,2,3-triazole derivatives in a unique 7a–g or hybrid form with isoxazoline 8a–g using the eugenol as a precursor in HT-1080 fibrosarcoma, MCF-7, and MDA-MB-231 breast carcinoma, and A-549 lung carcinoma. Data obtained on the cytotoxic effects have shown that hybrid compounds 8a–e induced a significant anticancer activity and are more important than the ones of 1,2,3-triazole derivatives 7a–g with IC50 ranging from 18 to 43 μM for the hybrids 8a–e and from 15 to 29 μM for mono-adducts 7a–g in all cell lines. Concerning the apoptotic study, compounds 7b and 8a can induce apoptosis in HT-1080 and A-549 cells as revealed by Annexin-V labeling and caspase-3/7 activity, also, the apoptotic effect was accompanied by cell cycle arrest at G2/M phase in the case of compounds 7b and 8a. Both compounds were evaluated in-silico through molecular docking and molecular dynamics and compound 8a is very active against Bcl-2 protein triggering apoptosis phenomenon by intrinsic pathway, therefore compound 8a is a potential candidate to inhibit the anti-apoptotic protein (Bcl-2). Communicated by Ramaswamy H. Sarma.
Synthesis, characterization, and biological evaluation of new heterocyclic systems 1, 2, 3-triazole-isoxazoline from eugenol by the mixed condensation reactions
Taia, Abdelmaoujoud,Essaber, Mohamed,Oubella, Ali,Aatif, Abdeljalil,Bodiguel, Jacques,Jamart-Grégoire, Brigitte,Ait Itto, My Youssef,Morjani, Hamid
, p. 2052 - 2065 (2020/05/14)
We report the synthesis of new series of heterocyclic systems eugenol 1 derivatives by the mixed condensation reaction of 1,3-dipolar azide and the oxide of p-chlorophenylnitrile on the 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene 2. The mono and bicycloadducts, whose structure is homologous to compounds having a broad spectrum of activity, were obtained in good yields. The monocondensation reaction of azides on 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene 2 is completely chemoselective, regioselective and stereospecific. The condensation of nitrile oxide on 1,2,3-triazole monocycloadducts prepared was chemoselective and regioselective. The structure of all cycloadducts were characterized and confirmed by the 1H, 13C, 2D nuclear magnetic resonance and mass spectrometry analysis. All the newly synthesized mono and bis-heterocyclic compounds have been selected for their antiproliferative activity against HT-1080 fibrosarcoma, A549 lung carcinoma, and MCF-7 and MDA-MB-231 breast carcinoma cell lines. Among the derivatives, only the compounds 4a, 4b, 5a, 5b, 5d, 5e and 5g showed significant cytotoxicity with IC50 values ranging from 15.31 to 18.81 μM against HT-1080 cells, and 17.32 to 25.94 μM against the other cell lines.
Raney Ni catalyzed azide-alkyne cycloaddition reaction
Surya Prakash Rao,Chakibanda, Guravaiah
, p. 46040 - 46048 (2015/02/19)
Raney Ni efficiently catalyzes acetylene azide cycloaddition reactions to form 1,2,3-triazoles. Unlike the CuSO4/sodium ascorbate reagent system, there is no need for a reducing agent under Raney Ni catalysis. Terminal acetylene selectivity, 1,
