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.
Rubrolides as Model for the Development of New Lactones and Their Aza Analogs as Potential Photosynthesis Inhibitors
Pereira, Ulisses A.,Barbosa, Luiz C. A.,Demuner, Ant?nio J.,Silva, Ant?nio A.,Bertazzini, Michele,Forlani, Giuseppe
, p. 987 - 1006 (2015)
Natural phytotoxins and their synthetic analogs are a potential source of new bioactive compounds for agriculture. Analogs of rubrolides, a class of γ-alkylidene-γ-lactones isolated from different ascidians, have been shown to interfere with the photosynthetic electron-transport chain, yet their activity needs to be improved. With this aim, ten 5-aryl-6-benzyl-4-bromopyridazin-3(2H)-ones were prepared in yields ranging from 44 to 88% by reaction of their correspondent γ-alkylidene-γ-lactones with NH2NH2. The structures of these rubrolide analogs were determined by 1H- and 13C-NMR, 2D-NMR (COSY and HETCOR), NOE difference, and MS techniques. These compounds were evaluated for their abilities of interfering with the light-driven reduction of ferricyanide by isolated spinach chloroplasts. Lactones with electron-withdrawing substituents in the para-position of the benzylidene ring were the most effective inhibitors. Characterization of the activity of 11b/11b′ suggested a mechanism based on the interaction with the plastoquinone binding site of photosystem II. Addition of several compounds to the culture medium of a cyanobacterial model strain was found to inhibit algal growth. However, the relative effectiveness was not consistent with their activity in vitro, suggesting the occurrence of multiple targets and/or detoxyfication mechanisms. Indeed, the compounds showed differential effects on the heterotrophic growth of some crop species, Cucumis sativus and Sorghum bicolor. Pyridazin-3(2H)-ones 12e, 12i, and 12j, which have been found poorly active against the photosynthetic electron transport, were the most effective in inhibiting the growth of some weeds, Ipomoea grandifolia and Brachiaria decumbens, under greenhouse conditions.
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.]
Inhibition of Enterococcus faecalis biofilm formation by highly active lactones and lactams analogues of rubrolides
Pereira, Ulisses A.,Barbosa, Luiz C.A.,Maltha, Célia R.A.,Demuner, Ant?nio J.,Masood, Mohammed A.,Pimenta, Andréa L.
, p. 127 - 138 (2014/06/23)
Seven β-aryl substituted γ-alkylidene-γ-lactones analogues of rubrolides were synthesized from mucobromic acid and converted through a lactamization with isobutylamine into their corresponding γ-hydroxy- γ-lactams (76-85%). These lactams were converted in
Synthesis of rubrolide analogues as new inhibitors of the photosynthetic electron transport chain
Barbosa, Luiz C. A.,Maltha, Célia R. A.,Lage, Mateus R.,Barcelos, Rosimeire C.,Donà, Alice,Carneiro, José W. M.,Forlani, Giuseppe
, p. 10555 - 10563 (2013/01/15)
Many natural products have been used as a model for the development of new drugs and agrochemicals. Following this strategy 11 rubrolide analogues, bearing electron-withdrawing and -donating groups at both benzene rings, were prepared starting from commercially available mucobromic acid. The ability of all compounds to inhibit the photosynthetic electron transport chain in the chloroplast was investigated. The rubrolide analogues were effective in interfering with the light-driven ferricyanide reduction by isolated chloroplasts. The IC50 values of the most active derivatives are in fact only 1 order of magnitude higher than those of commercial herbicides sharing the same mode of action, such as Diuron (0.27 μM). QSAR studies indicate that the most efficient compounds are those having higher ability to accept electrons, either by a reduction process or by an electrophilic reaction mechanism. The results obtained suggest that the rubrolide analogues represent promising candidates for the development of new active principles targeting photosynthesis to be used as herbicides.
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.
Synthesis of 3-bromotetronamides via amination of 3,4-dibromofuran-2(5H)- one
Cunha, Silvio,Oliveira, Caio C.,Sabino, Jose? R.
scheme or table, p. 598 - 603 (2011/10/17)
This work describes the direct synthesis of 3-bromotetronamides in good yields through the reaction of 3,4-dibromofuran-2(5H)-one, obtained from furfural, with primary and secondary amines. Aromatic amines were more tolerated than aliphatic and heteroaromatic ones. The X-ray structures of five derivatives are described.
Preparation of aryl-substituted butenolides using mucohalic acids
-
Page/Page column 6, (2008/06/13)
Methods and materials for preparing 3-aryl-2-buten-4-olides and 2,3-bisaryl-2-buten-4-olides are disclosed. The methods include reacting a mucohalic acid with a reducing agent to give a 2,3-dihalo-2-buten-4-olide, which undergoes at least one Pd catalyzed cross-coupling reaction with an arylboronic acid.
Reinvestigation of mucohalic acids, versatile and useful building blocks for highly functionalized alpha,beta-unsaturated gamma-butyrolactones.
Zhang,Blazecka, Peter G,Belmont, Daniel,Davidson, James G
, p. 4559 - 4561 (2007/10/03)
[reaction: see text] Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.
Selective synthesis of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones
Bellina, Fabio,Anselmi, Chiara,Viel, Stéphane,Mannina, Luisa,Rossi, Renzo
, p. 9997 - 10007 (2007/10/03)
4-Aryl-3-bromo-2(5H)-furanones have been selectively synthesized in satisfactory yields by treatment of easily available 3,4-dibromo-2(5H)-furanone either with arylboronic acids in the presence of Ag2O and a catalytic amount of PdCl2(MeCN)2 or with aryl(trialkyl)stannanes in the presence of a catalyst precursor consisting of AsPh3 and a Pd(II) or a Pd(0) compound. These monobromo derivatives have been then used as precursors to a variety of (Z)-4-aryl-5-[1-(aryl)methylidene]-3-bromo-2(5H)-furanones including the compound with the structure corresponding to that reported for naturally occurring rubrolide N. The structure and stereochemistry of these synthetic compounds have been unambiguously established by NMR techniques.
