In:
Journal of Heterocyclic Chemistry, Wiley, Vol. 58, No. 12 ( 2021-12), p. 2334-2347
Abstract:
A new 1,2,3‐triazole sesquiterpenic named (4aR,5aS,7aR,10aR,10bR)‐10‐benzyl‐5,5‐dichloro‐1,1,4a,7a‐tetramethyl‐1,2,3,4,4a,5,7a,10,10a,10b decahydrocyclopropa[2′,3′]cyclohepta [1′,2′:3,4] benzo[1,2‐d][1,2,3] triazol‐7(6H)‐one was synthesized by a dipolar cycloaddition 1,3 between benzyl azide and α,β‐unsaturated sesquiterpene ketone catalyzed by titanium tetrachloride TiCl 4 . It was obtained with a good yield and characterized using single‐crystal X‐ray diffraction technique, infra red (IR) spectroscopy, High Resolution Mass Spectrometry (HRMS), UV‐Visible, and 1 H and 13 C NMR spectroscopies. The optimization by the density functional theory (DFT) method was carried out to study the formation mechanism of the derivative. The selected compounds 1 – 4 exhibited anticancer activities in vitro against namely fibrosarcoma (HT‐1080), lung carcinoma (A‐549), and breast (MCF‐7 and MDA‐MB‐231 cell lines with IC 50 in the range of 10.02–44.71 μM). In addition to using flow cytometry and the apoptosis assay, cell cycle arrest at the S phase (10 μM) and G2/M arrest in (5 and 10 μM) was performed for compound 4 in fibrosarcoma (HT‐1080) cancer cells. Results suggested that compound 4 test with good activity against HT‐1080 cells with IC 50 value from 10.02 μM and induced the apoptotic effect. Theoretical studies were realized to estimate the molecular proprieties that lead to a high potential of cytotoxic effect, which is in agreement with the experimental results.
Type of Medium:
Online Resource
ISSN:
0022-152X
,
1943-5193
Language:
English
Publisher:
Wiley
Publication Date:
2021
detail.hit.zdb_id:
2042274-X
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