Evaluation of 1,3-benzoxathiol-2-one Derivatives as Potential Antifungal Agents

Terra, Luciana; Chazin, Eliza de Lucas; Sanches, Paola de S.; Saito, Max Seidy; Souza, Marcus V. N. de; Gomes, Cláudia R. B.; Wardell, Jámes L.; Wardell, Solange M. S. V.; Sathler, P.C; Silva, Gabriela C C; Lione, Viviane O; Kalil, Marcos; Joffily, Ana; Castro, Helena C.; Vasconcelos, Thatyana R. A.

doi:10.2174/1573406413666170704095113

Cited by 3 publications

(6 citation statements)

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“…Protocols for the preparation, physical and spectroscopic data of the compounds 2,5-7, 9-11, 1,14aq have already been reported in our previous studies. 13,14 2.1.1.1. Synthesis of 6-ethoxy-5-nitrobenzo [d] [1,3]oxathiol-2-one (8) Potassium carbonate (4 mmol) was added to a solution of 6-hydroxy-5-nitrobenzo[d] [1,3]oxathiol-2-one 2 (5 mmol) in DMF (18 mL).…”

Section: Chemistrymentioning

confidence: 99%

“…1,3-Benzoxathiol-2-one derivatives 1,2,5-14 were prepared as shown in Figure 3. 13,14 Commercially available 6-hydroxy-benzo[d] [1,3] oxathiol-2-one 4 was submitted to selective nitration at position 5 leading to the intermediate 2. Nitro derivative 2 was converted to derivatives 5, 6, 8 and 10 through catalytic hydrogenation, methylation, ethylation and acetylation conditions, respectively.…”

Section: Chemistrymentioning

confidence: 99%

“…The synthesis and characterization of the 1,3-benzoxathiol-2-one derivatives 5-7, 9-11 and 1,14a-q ( Figure 3) and 1,3-benzothiazole compounds, 3, 16a-l,n-q and 17a-c (Figure 4) have already been reported in our previous studies. [13][14][15][16]18 3.2. Biological assays…”

Section: Chemistrymentioning

confidence: 99%

“…On the other hand, significant antifungal activity was exhibited by compounds 2 and 10, highlighting derivative 2 with MIC value of 4 µg mL -1 (compared to ketoconazole) against C. krusei. 14 In this study, in vitro antimicrobial screening of derivatives 1,14a-q, 3, 16a-q and 17a-c was performed using the same seven bacterial strains and five Candida strains previously mentioned. Results, expressed as inhibitory growing zone diameters (halo = mm), pointed to 1,3-benzoxathiol-2-one derivatives 1, 14c, 14d and 14n, as well as 1,3-benzothiazole derivatives 16h, 16j, 16k, 16l and 16m, as having antimicrobial activity against some Gram-positive, Gram-negative or Candida strains ( Table 2).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…[9][10][11][12] In the last few years, our research group has been engaged in the synthesis of potentially bioactive compounds containing these two important classes of heterocycles. [13][14][15][16][17][18][19] We have synthesized a series of 1,3-benzoxathiol-2-one derivatives as potential anticancer agents, 13 and results pointed out compound 1 as the most active against melanoma . More recently, we have reported the synthesis of 1,3-benzoxathiol-2-one-based compounds and their antifungal activity against five Candida species.…”

Section: Introductionmentioning

confidence: 99%

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1,3-Benzoxathiol-2-one and 1,3-Benzothiazole Compounds as Potential Anticancer and Antimicrobial Agents

Vasconcelos

2020

Rev. Virtual Quim.

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Benzoxatiol-2-onas e 1,3-Benzotiazóis como Potenciais Agentes Anticâncer e Antimicrobianos Resumo: Ao longo dos anos, o câncer e as doenças infecciosas aparecem entre as principais causas de morte no mundo. Esses dados destacam a necessidade de novos protótipos para o desenvolvimento de quimioterápicos mais potentes e seletivos, bem como novos agentes antimicrobianos. O principal objetivo deste trabalho foi avaliar as atividades anticâncer, antibacteriana e antifúngica de alguns derivados 1,3-benzoxatiol-2-ona e 1,3-benzotiazol. Os compostos foram testados quanto à atividade anticâncer in vitro frente às linhagens de células de câncer de melanoma (SKMEL-19, de líquido ascítico (AGP-01 e de mama (MCF-7 pelo ensaio MTT. O perfil de toxicidade contra eritrócitos e fibroblastos humanos normais (MRC-5 também foi avaliado. Além disso, foram realizados ensaios in vitro de triagem antimicrobiana (TSA, concentração inibitória mínima (CIM, concentração bactericida mínima (CBM e concentração fungicida mínima (CFM contra bactérias Gram-positivas e Gramnegativas, bem como contra espécies do gênero Candida. Todos os testes foram realizados de acordo com os protocolos CLSI, utilizando vancomicina, ciprofloxacina e cetoconazol como fármacos de referência. O derivado 6-metoxi-benzo[d][1,3]oxatiol-2-ona (7) exibiu atividade citotóxica considerável (CI 50 = 3,3 μM) contra SKMEL-19 e o derivado (E)-4-((2-(benzo[d]tiazol-2-il) hidrazonometil)benzeno-1,2,3-triol (16m mostrou boa atividade contra todas as espécies de Candida (CIM 8-32 µg mL-1). A razão CBM/CIM dos derivados 16l e 16m os classificou como agentes bactericidas contra bactérias Gram-positivas. A substância 16m apresentou perfil fungistático contra Candida albicans e também espécies não albicans. De maneira geral, os resultados in vitro apontaram o potencial dos derivados 7 e 16m como novos protótipos anticâncer e antifúngico, respectivamente, para serem mais explorados, uma vez que também apresentaram baixo perfil de toxicidade.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Antimicrobial Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1,3-Benzoxathiol-2-one and 1,3-Benzothiazole Compounds as Potential Anticancer and Antimicrobial Agents

Vasconcelos

2020

Rev. Virtual Quim.

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Domino Cyclization/Trifluoromethylation of 2‐Alknylphenols for the Synthesis of 3‐(Trifluoromethyl)benzofurans and Evaluation of their Antibacterial and Antifungal Activities

et al. 2018

Asian J Org Chem

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Herein, we describe a one‐step synthesis of pharmaceutically relevant 3‐(trifluoromethyl)benzofurans from readily accessible 2‐alkynylphenols. The method utilizes a domino cyclization/trifluoromethylation strategy with [CuCF3] as a reagent. The CF3 source is the low‐cost industrial byproduct fluoroform (CF3H). The assays for antifungal and antibacterial activities conducted on these fluorinated benzofuran derivatives revealed that all were devoid of hemolytic activity toward rabbit erythrocytes indicating absence of toxicity. One of the compounds, 2 g, containing a 4‐NH2C6H4 moiety at the C‐2 position of the benzofuran core, demonstrated suppressive activity against the fungal pathogens Candida albicans, C. glabrata, and the bacterium methicillin‐resistant Staphylococcus aureus, showing minimal inhibitory concentrations (MICs) of 64 μM, 128 μM, and 128 μM, respectively. Incubation of Candida cells with 2 g elicited a time‐dependent accumulation of reactive oxygen species (ROS).

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Investigation of the monoamine oxidase inhibition properties of benzoxathiolone derivatives

et al. 2023

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The treatment of neuropsychiatric and neurodegenerative disorders such as depression and Parkinson’s disease represent significant challenges in healthcare. Enzymes that metabolise neurotransmitter amines are important drug targets for these disorders and inhibitors of these enzymes have played key roles as therapeutic agents. For example, inhibitors of monoamine oxidase (MAO) A have been used for decades as antidepressant agents and act by inhibiting the central metabolism of serotonin and noradrenaline, while MAO-B inhibitors conserve central dopamine supply and have been used to treat Parkinson’s disease. Literature reports that benzoxathiolone derivatives act as potent MAO inhibitors with specificity for the MAO-B isoform. To expand on these findings, the present study synthesised series of benzoxathiolone derivatives and investigated their human MAO inhibition properties. The results showed that the benzoxathiolone derivatives were potent MAO inhibitors, with the most potent compounds exhibiting IC50 values of 0.083 and 0.086 µM (4d and 5e) and 0.0069 and 0.0066 µM (3a and 3b) for MAO-A and MAO-B, respectively. Compounds 4d and 5e are significantly more potent MAO-A inhibitors compared to those reported previously. It may be concluded that benzoxathiolone derived compounds may act as future leads for the development of new treatments for depression and Parkinson’s disease. Graphical Abstract

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Evaluation of 1,3-benzoxathiol-2-one Derivatives as Potential Antifungal Agents

Abstract: Overall, the in vitro results pointed to the potential of compounds 2 and 7 as new antifungal prototypes to be further explored.

Cited by 3 publications

References 0 publications

1,3-Benzoxathiol-2-one and 1,3-Benzothiazole Compounds as Potential Anticancer and Antimicrobial Agents

1,3-Benzoxathiol-2-one and 1,3-Benzothiazole Compounds as Potential Anticancer and Antimicrobial Agents

Domino Cyclization/Trifluoromethylation of 2‐Alknylphenols for the Synthesis of 3‐(Trifluoromethyl)benzofurans and Evaluation of their Antibacterial and Antifungal Activities

Investigation of the monoamine oxidase inhibition properties of benzoxathiolone derivatives

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