109621-28-5Relevant articles and documents
Exploration of Benzo[b]carbazole-6,11-diones as anticancer agents: Synthesis and studies of hTopoIIα inhibition and apoptotic effects
Banerjee, Uttam C.,Chaudhary, Hiteshkumar,Daniel, Divine P,Das, Biswajit,Grewal, Preeti,Guchhait, Sankar K.,Kumar, Gulshan,Kundu, Chanakya N.,Nayak, Deepika,Paul, Subarno,Sisodiya, Shailendra
, (2021)
Two series of (hetero)arylamino-naphthoquinones and benzo-fused carbazolequinones were considered for study with the rationale that related structural motifs are present in numerous drugs, clinical trial agents, natural products and hTopoIIα inhibitors. Total 42 compounds were synthesized by reactions including dehydrogenative C–N and Pd-catalyzed C–C bond forming transformations. These compounds were screened against numerous cancer cells including highly metastatic one (MCF-7, MDA-MB-231, H-357 and HEK293T), and normal cells (MCF 10A). Some of the active compounds were evaluated for clonogenic cell survival and apoptotic effects in cancer cells (DAPI nuclear staining, Comet assay, Annexin-V-FITC/PI dual staining, flow cytometry, and western blot analysis with relevant proteins). All compounds were tested for hTopoIIα inhibitory activity. The investigated series compounds showed important properties like significant apoptotic antiproliferation in cancer cells with cell cycle arrest at S-phase and downregulation of NF- κβ signaling cascade, relatively less cytotoxicity to normal cells, and hTopoIIα inhibition with more efficiency compared to an anticancer drug etoposide.
In vitro inhibition of Helicobacter pylori growth by redox cycling phenylaminojuglones
Benites, Julio,Toledo, Héctor,Salas, Felipe,Guerrero, Angélica,Rios, David,Valderrama, Jaime A.,Buc Calderon, Pedro
, (2019/06/07)
Infection by Helicobacter pylori increases 10 times the risk of developing gastric cancer. Juglone, a natural occurring 1,4-naphthoquinone, prevents H. pylori growth by interfering with some of its critical metabolic pathways. Here, we report the design, synthesis, and in vitro evaluation of a series of juglone derivatives, namely, 2/3-phenylaminojuglones, as potential H. pylori growth inhibitors. Results show that 5 out of 12 phenylaminojuglones (at 1.5 μg/mL) were 1.5–2.2-fold more active than juglone. Interestingly, most of the phenylaminojuglones (10 out of 12) were 1.1–2.8 fold more active than metronidazole, a known H. pylori growth inhibitor. The most active compound, namely, 2-((3,4,5-trimethoxyphenyl)amino)-5-hydroxynaphthalene-1,4-dione 7, showed significant higher halo of growth inhibitions (HGI = 32.25 mm) to that of juglone and metronidazole (HGI = 14.50 and 11.67 mm). Structural activity relationships of the series suggest that the nature and location of the nitrogen substituents in the juglone scaffold, likely due in part to their redox potential, may influence the antibacterial activity of the series.
Ultrasonic and microwave assisted synthesis of nitrogen-Containing derivatives of juglone as potential antibacterial agents
Lopez-Lopez, Lluvia Itzel,Garcia, Jesus Javier Vaquera,Saenz-Galindo, Aide,Silva-Belmares, Sonia Yesenia
, p. 573 - 582 (2014/07/21)
Ultrasound and microwave assisted expedient synthesis of potential antibacterial compounds, 2-(anilino)-5- hydroxy-1,4-Naphthoquinone derivatives 3a-C and 5-hydroxybenzo[f]indole-4,9-dione derivatives 8a-C and 10- hydroxybenzo[b]carbazole-6,11-dione derivatives 9a-C have been developed. For the preparation of 3a-Cderivatives the methods Room Temperature Synthesis (RTS), Conventional Heating Synthesis (CHS) and Ultrasound Assisted Synthesis(UAS) were performed. In addition, the Conventional Synthesis (CS) and Microwave Assisted Synthesis (MAS)were used for 8a-C and 9a-C derivatives. UAS and MAS showed the best results and are considered greenalternatives of synthesis. In general, the yields obtained were good to excellent (58 to 93%). In addition, antibacterial activity against five bacterial strains was tested, showing bacteriostatic activity at lower concentrations and greaterbactericidal against Gram negative strains. The compounds carrying chlorine atoms at 2 and 4 positions on the phenyl ring were the most active. The results obtained indicate that the 1,4-Naphthoquinone derivatives presented here have promising use as antibacterial agents. A reaction mechanism is also proposed. 2014 Bentham Science Publishers.
