Synthesis, Crystal Structure and Anti-Leukemic Activity of 1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one

Abstract

1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new substituted pyrrolo[1,2-a]quinoxaline compound was achieved by using FT-IR, 1H-NMR, 13C-NMR, X-Ray and HRMS spectral analysis. This new pyrroloquinoxaline derivative shows an interesting cytotoxic potential against several human leukemia cell lines (HL60, K562 and U937 cells).

Crystal structure, Hirshfeld surface analysis, calculations of intermolecular interaction energies and energy frameworks and the DFT-optimized molecular structure of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one

“…Heterocyclic compounds comprising the benzimidazolone fragment have attracted interest due to their remarkable usefulness in various therapeutic applications. Extensive research has revealed several pharmacological and biological properties associated with these compounds, including antiproliferative (Guillon et al, 2022), antibacterial (Al-Ghulikah et al, 2023;Saber et al, 2020), anticancer (Dimov et al, 2021) and antiviral (Ferro et al, 2017) activities.…”

Synthesis, structure and Hirshfeld surface analysis of 1,3-bis[(1-octyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazol-2(3H)-one

“…Benzimidazolone derivatives display diverse pharmacological and biological properties including antiviral (Ferro et al, 2017), antibacterial (Saber et al, 2020;Mentes ¸e et al, 2021), anticancer (Guillon et al, 2022), anti-Alzheimer's (Mo et al, 2020), antifungal (Ibrahim et al, 2021), and antioxidant (Ibrahim et al, 2021) activities. In our ongoing research in this area, we are synthesizing compounds that combine the 1,2,3triazole motif with benzimidazol-2-one derivatives.…”

Synthesis, Crystal Structure and Anti-Leukemic Activity of (E)-Pyrrolo[1,2-a]quinoxalin-4-yl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

“…Cell proliferation assays were performed using MTS tetrazolium (Cell Titer96 Aqueous; Promega, Charbonnières-les-Bains, France) on the human leukemic cell lines K562, MV4-11, Jurkat and MOLM14 as previously described by our team [16,17,21]. Cells (10 5 ) were plated in quadruplicate into microtiter-plate wells in 100 µL of culture medium with various doses of compounds (1; 5; 10; 20; 50 µM).…”

“…[1,2]. Thus, many pyrrolo[1,2-a]quinoxaline compounds have been designed, synthesized and described as antipsychotic agents [3], antiviral agents [4], adenosine receptor modulators [5], antituberculosis agents [6,7], antiparasitic [8][9][10][11][12][13][14][15] and anticancer compounds [16][17][18][19][20][21][22]. However, despite the recent and promising development of targeted therapies, there is still a need to discover new cytotoxic molecules for the treatment of human cancers.…”

“…We previously published a series of new pyrrolo [1,2-a]quinoxaline derivatives endowed with promising pharmacological activity towards human leukemia cells [16][17][18][19][20][21]. In this context, and as an extension of our research work on the development and assessment of new antiproliferative heterocyclic derivatives, we decided to further modulate and substitute our heterocyclic pyrrolo [1,2-a]quinoxaline pharmacophore.…”