3919-49-1

Usage

InChI:InChI=1/C14H11NO/c1-9-8-13(16)12-7-6-10-4-2-3-5-11(10)14(12)15-9/h2-8H,1H3,(H,15,16)

Upstream product

• 134-32-7 1-amino-naphthalene 
• 141-97-9 ethyl acetoacetate 
• 118176-47-9 3-[1]naphthylamino-crotonic acid ethyl ester 

Relevant academic research and scientific papers

Dinaphthonaphthyridines - A class of novel molecules with potent antioxidant and anticancer activity

A series of novel dinaphtho[1,2-b:1′,2′-h][1,6]naphthyridine derivatives bearing aliphatic, aromatic and heteroaromatic substituents at the C7 position were designed and synthesized conveniently from 4-chloro-2-methylbenzo[h]quinoline. All compounds were screened for in vitro antioxidant activities against DPPH, ABTS+, superoxide and hydroxyl radicals. Among the compounds screened, 13, 15, 16, 19 and 20 showed excellent antioxidant activity against OH. In addition, the cytotoxicity of the dinaphthonaphthyridine derivatives was evaluated by MTT assay and compared with Adriamycin. From screening, we identified that compounds 6, 16 and 20 showed IC50s ranging from 1.20 to 5.61 μM for growth inhibition of HeLa, HCT116 and AGS cancer cell lines. The results documented that varying of the chemical entity at C7 can fine-tune the enhancement of cell growth inhibition strategy. The Royal Society of Chemistry.

Syntheses and characterization of non-bisphosphonate quinoline derivatives as new FPPS inhibitors

Background Farnesyl pyrophosphate synthase (FPPS) is a key regulatory enzyme in the biosynthesis of cholesterol and in the post-translational modification of signaling proteins. It has been reported that non-bisphosphonate FPPS inhibitors targeting its allosteric binding pocket are potentially important for the development of promising anti-cancer drugs. Methods The following methods were used: organic syntheses of non-bisphosphonate quinoline derivatives, enzyme inhibition studies, fluorescence titration assays, synergistic effect studies of quinoline derivatives with zoledronate, ITC studies for the binding of FPPS with quinoline derivatives, NMR-based HAP binding assays, molecular modeling studies, fluorescence imaging assay and MTT assays. Results We report our syntheses of a series of quinoline derivatives as new FPPS inhibitors possibly targeting the allosteric site of the enzyme. Compound 6b showed potent inhibition to FPPS without significant hydroxyapatite binding affinity. The compound showed synergistic inhibitory effect with active-site inhibitor zoledronate. ITC experiment confirmed the good binding effect of compound 6b to FPPS, and further indicated the binding ratio of 1:1. Molecular modeling studies showed that 6b could possibly bind to the allosteric binding pocket of the enzyme. The fluorescence microscopy indicated that these compounds could get into cancer cells. Conclusions Our results showed that quinoline derivative 6b could become a new lead compound for further optimization for cancer treatment. General significance The traditional FPPS active-site inhibitors bisphosphonates show poor membrane permeability to tumor cells, due to their strong polarity. The development of new non-bisphosphonate FPPS inhibitors with good cell membrane permeability is potentially important.

Microwave-assisted Synthesis of 2-methyl-4-quinolinones via combes synthesis catalyzed by acidic resin under solvent-free condition

A simple and efficient method for the synthesis of 2-methylquinolin-4(1H)- one derivatives using NKC-9-resin as reusable eco-friendly catalyst via Combes cyclization under solvent-free and microwave irradiation conditions is described. The quinolines were obtained in high yields and in short reaction times.