149418-41-7Relevant articles and documents
An efficient and inexpensive multigram synthesis of 3,4-dibromo- and 3,4-dichlorofuran-2(5H)-one
Bellina, Fabio,Rossi, Renzo
, p. 1887 - 1889 (2007)
The efficient and inexpensive synthesis of 3,4-dibromo- and 3,4-dichlorofuran-2(5H)-one on a multigram scale by sodium borohydride reduction of mucobromic and mucochloric acid, respectively, is reported. Georg Thieme Verlag Stuttgart.
Synthesis and cytotoxic evaluation of halogenated furanones
Castro-Torres, Víctor A.,Jacobo-Herrera, Nadia J.,Díaz-Sánchez, Lidia,Rocha-Zavaleta, Leticia,García-López, Patricia,Martínez-Vázquez, Mariano
, p. 1841 - 1849 (2020/11/10)
Abstract: The objective of the current study is to evaluate the potency of halogen-furan-2(5H)-one-type derivatives against human cancer cell lines. Four known bromofuran-2(5H)-one-type derivatives, as well as five new and two known bromo-4-(phenylamino)furan-2(5H)-one-type compounds and six novel and two known halogen-4-alkyl-5-phenyl-3-(phenylamino)furan-2(5H)-one-type derivatives, were synthesized and evaluated for their anticancer activity against prostate (PC-3) and colon (HCT-116) human cancer cell lines. The results showed that only the bromofuran-2(5H)-ones were cytotoxic in both cell lines. Three of these displayed particularly useful antiproliferative activities, in both cancer cells evaluated. (E)-5-(Bromomethylene)furan-2-(5H)-one was the most active against PC-3 (IC50 0.93 ± 0.02?μM) while 3,4-dibromofuran-2(5H)-one was the most active against HCT-116 (IC50 0.4 ± 0.04?μM). Furthermore, flow cytometry studies revealed that the bromofuran-2(5H)-ones induced cell death by apoptosis. Also, it was found that the cytotoxic furanones induced lipid peroxidation, determined by TBARS assay. Thus, cytotoxicity of the active compounds could be associated with ROS production. Additionally, it must be taken into account that all cytotoxic compounds contain an electrophilic carbon atom in position 4, which can explain, through a non-specific reactivity with nucleophiles, the cytotoxic activity of these compounds. Graphic abstract: [Figure not available: see fulltext.]
Synthesis, Molecular Docking, and Biofilm Formation Inhibitory Activity of 5-Substituted 3,4-Dihalo-5H-furan-2-one Derivatives on Pseudomonas aeruginosa
Liu, Guo-Yong,Guo, Bao-Qin,Chen, Wan-Na,Cheng, Chao,Zhang, Qian-Lan,Dai, Mi-Bei,Sun, Jun-Rong,Sun, Ping-Hua,Chen, Wei-Min
scheme or table, p. 628 - 638 (2012/06/18)
Pseudomonas aeruginosa (P. aeruginosa) colonize on most wounds and live as biofilm, which causes antibiotic resistance and wounds unhealed. To investigate the effects of 5-substituted 3,4-dihalo-5H-furan-2-one compounds on biofilm formation of P. aeruginosa, a set of 5-(aryl-1′-hydroxy-methyl)- or 5-(aryl-2-methylene)-3,4-dihalo-5H-furan-2-one compounds were designed and synthesized. Their inhibitory activities on biofilm formation of P. aeruginosa were studied by MIC assay, quantitative analysis of biofilm inhibition, and observation of biofilm formation with SEM. It was found that compounds 2i, 3f, 3i showed remarkable effects of biofilm formation inhibition on P. aeruginosa. Furthermore, molecular docking was performed to identify the key structural features of these compounds with the binding site of LasR receptor.