Synthesis and Antifungal Activity of Derivatives of 2- and 3-Benzofurancarboxylic Acids

Hejchman, Elżbieta; Ostrowska, Kinga; Maciejewska, Dorota; Kossakowski, Jerzy; Courchesne, William E.

doi:10.1124/jpet.112.196980

Cited by 18 publications

(10 citation statements)

References 52 publications

(54 reference statements)

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“…One of such compounds (denominated 4 in this previous report) was able to completely arrest C. neoformans growth at a concentration of 20 µM, while it affected human leukemia K-562 cells only at concentrations higher than 30 µM. Interestingly, this drug was able to enhance the Ca 2+ mobilization produced by amiodarone in yeast (Hejchman et al, 2012).…”

Section: Introductionmentioning

confidence: 88%

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Anti-Trypanosoma cruzi action of a new benzofuran derivative based on amiodarone structure

Pinto-Martinez

Hernández-Rodríguez

Rodríguez-Durán

et al. 2018

Experimental Parasitology

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Chagas disease is a neglected tropical affection caused by the protozoan parasite Trypanosoma cruzi. There is no current effective treatment since the only two available drugs have a limited efficacy and produce side effects. Thus, investigation efforts have been directed to the identification of new drug leads. In this context, Ca regulating mechanisms have been postulated as targets for antiparasitic compounds, since they present paramount differences when compared to host cells. Amiodarone is an antiarrhythmic with demonstrated trypanocidal activity acting through the disruption of the parasite intracellular Ca homeostasis. We now report the effect of a benzofuran derivative based on the structure of amiodarone on T. cruzi. This derivative was able to inhibit the growth of epimastigotes in culture and of amastigotes inside infected cells, the clinically relevant phase. We also show that this compound, similarly to amiodarone, disrupts Ca homeostasis in T. cruzi epimastigotes, via two organelles involved in the intracellular Ca regulation and the bioenergetics of the parasite. We demonstrate that the benzofuran derivative was able to totally collapse the membrane potential of the unique giant mitochondrion of the parasite and simultaneously produced the alkalinization of the acidocalcisomes. Both effects are evidenced by a large increase in the intracellular Ca concentration of T. cruzi.

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Section: Introductionmentioning

confidence: 88%

“…1. Chemical structure of (A) the benzofuran derivative (AMIODER), based on the structure of (B) amiodarone, used in this work (Hejchman et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Anti-Trypanosoma cruzi action of a new benzofuran derivative based on amiodarone structure

Pinto-Martinez

Hernández-Rodríguez

Rodríguez-Durán

et al. 2018

Experimental Parasitology

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“…Oxygen containing heterocycles possess many biological activities, such as anti-inflammatory [75], anticancer [76], antioxidative [77], antiviral [78] and antifungal activity [79]. It was a major challenge for organic chemists to synthesize heterocyclic compounds with a high degree of selectivity, specially the benzo[b]furan from a simple synthon.…”

Section: In 2009mentioning

confidence: 99%

Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review

et al. 2020

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Sonogashira coupling involves coupling of vinyl/aryl halides with terminal acetylenes catalyzed by transition metals, especially palladium and copper. This is a well known reaction in organic synthesis and plays a role in sp2-sp C-C bond formations. This cross coupling was used in synthesis of natural products, biologically active molecules, heterocycles, dendrimers, conjugated polymers and organic complexes. This review paper focuses on developments in the palladium and copper catalyzed Sonogashira cross coupling achieved in recent years concerning substrates, different catalyst systems and reaction conditions.

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“…Also, recent studies showed that novel 1,4,5,6,7,8-hexahydroquinoline derivatives have significant cytotoxic activity against different human cancer cell lines [10][11][12]. Also, literature survey documented that various benzofuran compounds are known to possess important biological properties, including antimicrobial [13][14][15], antifungal [16], antiviral [17], anti-inflammatory [18,19], antidiabetic [20], antioxidant [21,22]. Moreover, many benzofuran derivatives have shown remarkable anticancer activity [23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety

2015

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A series of new ethyl 4-(2-(benzofuran-2-yl)-4-substituted-1,4,5,6,7,8-hexahydroquinolin-1-yl)-benzoate 3a-c was synthesized by Michael condensation of benzofuran chalcones 1a-c and cyclohexanone to give 2-(2-benzofuranyl)-4-substituted-5,6,7,8-tetrahydro-4-H -chromene 2a-c, followed by reaction of the latter with ethyl 4-aminobenzoate. Condensation of 3a-c with different amines afforded the corresponding amides 4a-e. On the other hand, upon treatment compounds 3a-c with hydrazine hydrate gave the benzohydrazide derivatives 5a-c. The reaction of compounds 5a-c with different thio/isocyanate gave the corresponding thiosemicarbazide and semicarbazide derivatives 6a-c. Meanwhile compounds 5a-c were reacted with ethyl cyanoacetate and different b-dicarbonyl compounds such as acetyl acetone, ethyl acetoacetate, and diethyl malonate to afford pyrazolyl derivatives 7a, b; 8a, b; 9a, b; and 10a-c, respectively. Moreover, 5a-c were reacted with carbon disulfide to synthesize the corresponding oxadiazolyl derivatives 11a-c, while their condensation with different aromatic aldehydes gave the corresponding Schiff bases 12a-d. Cytotoxic evaluation of some of the newly synthesized compounds against human hepatocellular carcinoma cell lines (HepG-2) revealed that the tested compounds produce promising inhibitory effect against the growth of HepG-2 cells with IC 50 values ranged from 11.9 to 19.3 lg/mL.

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Synthesis and Antifungal Activity of Derivatives of 2- and 3-Benzofurancarboxylic Acids

Abstract: We found that amiodarone has potent antifungal activity against a broad range of fungi, potentially defining a new class of antimycotics. Investigations into its molecular mechanisms showed amiodarone mobilized intracellular Ca 2ϩ

Cited by 18 publications

References 52 publications

Anti-Trypanosoma cruzi action of a new benzofuran derivative based on amiodarone structure

Anti-Trypanosoma cruzi action of a new benzofuran derivative based on amiodarone structure

Palladium and Copper Catalyzed Sonogashira cross Coupling an Excellent Methodology for C-C Bond Formation over 17 Years: A Review

Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety

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