Design, Synthesis and Structure–Activity Relationship Studies of Novel Spirochromanone Hydrochloride Analogs As Anticancer Agents

Abstract

Aim: Literature reports suggest spirochromanone derivatives exhibit anticancer activity. Methodology: The authors designed and synthesized 18 spirochromanone derivatives (Csp 1–18). The compounds were characterized and evaluated for anticancer activity against human breast cancer (MCF-7) and murine melanoma (B16F10) cell lines. Results: The anticancer activity ranged from 4.34 to 29.31 μm. The most potent compounds, Csp 12 and Csp 18, were less toxic against the human embryonic kidney (HEK-293) cell line and ∼ two/∼four fold selective toward MCF-7 than B16F10 in comparison to the reference, BG-45. Csp 12 caused 28.6% total apoptosis, leading to significant cytotoxicity, and arrested the G2 phase of the cell cycle in B16F10 cells. A molecular docking study of Csp 12 exhibited effective binding at the active site of the epidermal growth factor receptor kinase domain. Conclusion: This study highlights the importance of spirochromanones as anticancer agents.

Design, Synthesis and Biological Evaluation of Novel Spiro‐[Chroman‐2,4′‐Piperidin]‐4‐One Analogs as Anti‐Tubercular Agents

“…In this research, the analogs of spiro‐[chroman‐2,4′‐piperidin]‐4‐one ( PS01 – PS15 ) are synthesized as depicted in Scheme 1. The detailed synthetic procedure for each step and the corresponding analytical data are described in detail in the Supporting Information as well as in a recent article published by our group [40] …”

“…The detailed synthetic procedure for each step and the corresponding analytical data are described in detail in the Supporting Information as well as in a recent article published by our group. [40] Thin layer chromatography (TLC) and ESI mass spectrometry were used to monitor all the experiments. Column chromatography using silica gel (100-200 mesh size) and AcOEt in hexane as eluent was used to purify crude products from each step (10 % to 100 %).…”

Design, synthesis, and biological evaluation of novel quinoxaline aryl ethers as anticancer agents

“…There are only a few quinoxaline aryl ethers reported in the literature as anticancer agents (Abbas et al, 2015;Corona et al, 2009;Hazeldine et al, 2005;Tang et al, 2020;Xia et al, 2016), and there are no reports with quinoxine aryl ethers with anilides embedded as on date. Hence, in continuation to our ongoing research on anticancer activity (Chitti et al, 2021(Chitti et al, , 2022, and owing to the importance and novelty of these derivatives, we explored the anticancer potential of the quinoxaline aryl ether containing anilides.…”