A green synthesis, DFT calculations, and molecular docking study of some new indeno[2,1-b]quinoxalines containing thiazole moiety

• Published in: Journal of molecular structure 2023-11, Vol.1292, p.136044, Article 136044
• Main Authors: Abdallah, Abanoub Mosaad, Gomha, Sobhi M., Zaki, Magdi E.A., Abolibda, Tariq Z., Kheder, Nabila A.
• Format: Article
• Language: English
• Subjects: DFT calculations; Hydrazonoyl chlorides; Indeno[2,1-b]quinoxalines; Molecular docking; Thiazole
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.136044

•Novel indeno[2,1-b]quinoxalines containing thiazole moiety were reported.•Their structures were confirmed using various spectroscopic techniques.•DFT and TD-DFT calculations were applied on the investigated compounds.•Their anti-breast cancer activity were studied using molecular docking simulations. A series of new indenoquinoxaline-thiazole hybrids were synthesized by combining indenoquinoxaline thiosemicarbazone with appropriate hydrazonoyl chlorides or α-halo ketones using DABCO as a catalyst. The short reaction times and excellent yields make this method simple, green, and economic to synthesize new compounds with potential biological activities. FT IR, NMR, and MS spectrum data are some of the spectroscopic techniques used to confirm the structure of the synthesized hybrids. In addition, density functional theory (DFT) calculations were conducted to study the geometry optimization of some representative compounds, and their electronic transitions in DMSO were investigated by performing time-dependent DFT calculations. Additionally, a molecular docking study was carried out to investigate the possible interactions and binding mode of the newly synthesized compounds to the estrogen receptor (ER) binding site to estimate their anticancer activity against hormonally driven breast cancer. [Display omitted]