Newly synthesized (R)-carvone-derived 1, 2, 3-triazoles: structural, mechanistic, cytotoxic and molecular docking studies. Issue 16 (2nd November 2022)

• Record Type: Journal Article
• Authors: Hachim, Mouhi Eddine; Oubella, Ali; Byadi, Said; Fawzi, Mourad; Laamari, Yassine; Bahsis, Lahoucine; Aboulmouhajir, Aziz; Morjani, Hamid; Podlipnik, Črtomir; Auhmani, Aziz; Ait Itto, My Youssef
• Is Part Of: Journal of biomolecular structure & dynamics. Volume 40:Issue 16(2022)
• Page Start: 7205
• Page End: 7217
• Publication Date: 2022-11-02
• Subjects: (R)-Carvone -- 123-triazole -- Click chemistry -- Regioselectivity -- DFT calculation -- Molecular docking; Biomolecules -- Periodicals; Molecular structure -- Periodicals; Molecular Biology -- Periodicals; Biomechanics -- Periodicals; 572
• DOI: 10.1080/07391102.2021.1894984
• Languages: English
• ISSNs: 0739-1102

Abstract

Abstract: In the current study, natural (R)-carvone was used as starting material for the efficient synthesis of several 1, 2, 3-triazole derivatives. The produced products were obtained in good yields and characterized by 1 H and 13 C NMR and HRMS analysis. The newly synthesized monoterpenic 1, 2, 3-triazole 4 and derivatives were analyzed by viability tests (MTT) for their cytotoxic activity against three human cancer cells. Product 5 showed a medium antitumor activity, for which the IC50 values against selected cells HT-1080, A-549 and MCF-7 were 29.25 μM, 31.62 μM and 26.02 μM, respectively. The regioselectivity of the condensation reaction and the molecular structure of the title compounds were determined by Density Functional Theory (DFT) using B3LYP calculations at 6-311 + G(d, p) level. The orbitals HOMO and LUMO were studied to determine the electronic properties of the synthesized compounds. In addition, the global reactivity indices were used to explain the regioselectivity for the formation of compound 6, and the theoretical results agree well with the experimental results. Molecular docking and molecular dynamics confirmed the empirical test results and confirmed the stability of the complex during inhibition of the anti-apoptotic protein for killing cancer cells. Communicated by Ramaswamy H. Sarma Graphical abstract: UF0001