Synthesis and antibacterial activity of new symmetric polyoxygenated dibenzofurans

Oramas‐Royo, Sandra; Pantoja, Kriss Dayana; Amesty, Ángel; Romero, Carlos Dı́az; Lorenzo-Castrillejo, Isabel; Machín, Félix; Estévez‐Braun, Ana

doi:10.1016/j.ejmech.2017.09.062

Cited by 6 publications

(9 citation statements)

References 38 publications

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“…The choice of polyoxygenated dibenzofurans was consistent with the literature precedent pointing out that such structures are well-established sources of biologically active scaffolds in drug discovery [23][24][25][26]. Otherwise, usnic acid, a secondary metabolite isolated from lichens, with structural similarity with cercosporamide was described as a Pim-1/2 inhibitor and active against myeloid leukemia [27,28].…”

Section: Synthesissupporting

confidence: 62%

Dibenzofuran Derivatives Inspired from Cercosporamide as Dual Inhibitors of Pim and CLK1 Kinases

et al. 2021

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Pim kinases (proviral integration site for Moloney murine leukemia virus kinases) are overexpressed in various types of hematological malignancies and solid carcinomas, and promote cell proliferation and survival. Thus, Pim kinases are validated as targets for antitumor therapy. In this context, our combined efforts in natural product-inspired library generation and screening furnished very promising dibenzo[b,d]furan derivatives derived from cercosporamide. Among them, lead compound 44 was highlighted as a potent Pim-1/2 kinases inhibitor with an additional nanomolar IC50 value against CLK1 (cdc2-like kinases 1) and displayed a low micromolar anticancer potency towards the MV4-11 (AML) cell line, expressing high endogenous levels of Pim-1/2 kinases. The design, synthesis, structure–activity relationship, and docking studies are reported herein and supported by enzyme, cellular assays, and Galleria mellonella larvae testing for acute toxicity.

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Section: Synthesissupporting

confidence: 62%

Dibenzofuran Derivatives Inspired from Cercosporamide as Dual Inhibitors of Pim and CLK1 Kinases

et al. 2021

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“…We envision that this work will inspire more investigation of general synthesis of dibenzofurans from benzofurans. Moreover, given the important applications of dibenzofurans, [1][2][3][4][5][6] we expect the ones prepared with our methodology will find application in the fileds of material science and pharmaceutical research.…”

Section: Resultsmentioning

confidence: 99%

“…[1] A variety of dibenzofuran derivatives exhibit promising anticancer, anti-inflammatory, antimalarial, antibiosis and anti-diabetic activities. [2][3][4][5][6] Moreover, a class of dibenzofuran-4,6-bis(oxazoline) (DBFOX) ligands [7] have been developed for transition metal-catalyzed asymmetric synthesis. In this context, synthesis of dibenzofurans has aroused great interest in synthetic chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…Dibenzofuran structural motifs are found in natural products, pharmaceuticals, as well as organic functional materials . A variety of dibenzofuran derivatives exhibit promising anticancer, anti‐inflammatory, antimalarial, antibiosis and anti‐diabetic activities . Moreover, a class of dibenzofuran‐4,6‐bis(oxazoline) (DBFOX) ligands have been developed for transition metal‐catalyzed asymmetric synthesis.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Dibenzofurans Derivatives via Benzannulation of 2‐Nitrobenzofurans and Alkylidene Malononitriles

Cao

Chen

et al. 2020

Asian J Org Chem

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Although various methods for the preparation of dibenzofurans are available, an efficient, general synthesis of dibenzofurans from benzofurans remains an unsolved problem. Herein, we provide the first benzannulation of readily prepared 2-nitrobenzofurans with alkylidene malononitriles. This methodology enables facile assembly of a wide variety of highly functionalized dibenzofurans in moderate to excellent yields under metal-free conditions. Gram-scale synthesis and further elaborations of the product were succesfully performed, demonstrating synthetic utility of this method.

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“…Antibacterial activity was determined using the standard broth microdilution method as recommended by the National Committee for Clinical Laboratory Standards [ 8 , 11 , 25 ]. We used three Gram-positive bacterial strains; methicillin-sensitive Staphylococcus aureus ATCC25923 (MSSA), methicillin-resistant vancomycin-intermediate resistant Staphylococcus aureus NRS402 (VISA), and Enterococcus faecalis ATCC29212; as well as the Gram-negative Escherichia coli ATCC35218.…”

Section: Methodsmentioning

confidence: 99%

Efficient Multicomponent Synthesis of Diverse Antibacterial Embelin-Privileged Structure Conjugates

et al. 2020

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A library of embelin derivatives has been synthesized through a multicomponent reaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin, 4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities.

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Synthesis and antibacterial activity of new symmetric polyoxygenated dibenzofurans

Cited by 6 publications

References 38 publications

Dibenzofuran Derivatives Inspired from Cercosporamide as Dual Inhibitors of Pim and CLK1 Kinases

Dibenzofuran Derivatives Inspired from Cercosporamide as Dual Inhibitors of Pim and CLK1 Kinases

Synthesis of Dibenzofurans Derivatives via Benzannulation of 2‐Nitrobenzofurans and Alkylidene Malononitriles

Efficient Multicomponent Synthesis of Diverse Antibacterial Embelin-Privileged Structure Conjugates

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