Design, synthesis, and cytotoxic evaluation of novel furo[2,3‐b]quinoline derivatives

Abstract

A number of novel furo[2,3-b]quinoline derivatives were designed and synthesized by introducing benzyl ether, benzoate, and benzenesulfonate to 6-position of furo[2,3-b]quinoline and their chemical structures were confirmed by ESI-MS, H NMR, and C NMR spectra. All target compounds were evaluated in vitro against four human cancer cell lines (HCT-116, MCF-7, U2OS, and A549) by MTT method. Cytotoxic assay showed that compounds 8a, 8e, 10a, 10b, and 10c exhibited more potent cytotoxicities compared to 2-bromine-6-hydroxy-furo-[2,3-b]quinoline (7). Compound 10c exhibited higher antiproliferative activity (IC values ranging from 4.32 to 24.96 μm) against four human cancer cell lines (HCT-116, MCF-7, U2OS, and A549) and weak cytotoxicity on normal cell HL-7702, which suggested that 10c might be an ideal anticancer candidate. Compounds 8a, 10a, 10b showed good selectivities to MCF-7 and HCT-116, which could be considered as ideal selective candidates for further study. The SARs showed that the introduction of the benzyl ether and benzenesulfonate could significantly improve cytotoxicities, while the benzoate failed to enhance potency obviously.

Convenient Synthesis of Furo[3,2-b]quinolin-4(1H)-ones

“…4-Ethynyl- [1,3]dioxolo [4,5-c]quinolone (1) was used as the common starting material for the preparation of key intermediates 2-19. As previously reported, derivative 1 can be easily synthesized in few steps starting from anthranilic acid and chloroacetone, and its synthesis can even be scaled up to multigram quantities.…”

“…Furoquinolines are natural products 1 with a wide range of promising biological activities. Selected derivatives possess antiviral, 2 cytotoxic, 3 antitubercular, 4 or antimalarial 5 effects. This predestines furoquinolines for further structural modification to find potential therapeutics with improved pharmacological properties.…”

Molecular docking studies on COVID-19 and antibacterial evaluation of newly synthesized 4-(methoxymethyl)-1,2,3-triazolean analogues derived from (E)-1-phenyl-3-(2-(piperidin-1-yl)quinolin-3-yl) prop-2-en-1-one

“…A series of novel quinolone-based chalcones containing 1,2,3-triazole moiety were synthesized. Several natural products contain quinoline nucleus in (Cinchona Alkaloids) and quinoline analogues displaying a broad range of biological activities [ 1 ] such as anticytotoxic [ 2 ], antimicrobial [ 3 ], anti-tubercular [ 4 ] and anti-malarial [ 5 ]. Moreover, Chalcones are a class of privileged structures that have a wide range of biological properties such as antimicrobial [ 6 ], anti-inflammatory [ 7 ] and anticancer [ 8 ].…”

Novel Anthraquinone Compounds Inhibit Colon Cancer Cell Proliferation via the Reactive Oxygen Species/JNK Pathway

“…Despite being the current treatment of choice in many cases, chemotherapy still has many disadvantages, such as strong toxic side-effects and partial lack of targeting specificity [1][2][3]. Therefore, the design and synthesis of new compounds that act specifically on target proteins in tumor cells is a focus of current research [4][5][6]. Anthraquinone derivatives with a 9,10-anthracene skeleton are a class of natural compounds frequently used in traditional Chinese medicine.…”