Facile Synthesis of 2-Substituted Benzo[b]thiophen-3-ols in Water

Pan, Ben; Ren, Peng; Song, Haibin; Wang, Zhihong

doi:10.1080/00397911.2011.633203

Cited by 6 publications

(1 citation statement)

References 30 publications

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“…The structure of benzo[b]thiophen-3-ol has been previously studied from a chemical point of view and several research groups have proposed synthetic strategies to obtain this class of compounds [23][24][25] . Here, we propose a new one-step, very simple synthetic procedure which allowed us to obtain the desired compounds PM1-PM20 (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Benzo[b]tiophen-3-ol derivatives as effective inhibitors of human monoamine oxidase: design, synthesis, and biological activity

Guglielmi

Secci

Petzer

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of benzo[ b ]thiophen-3-ols were synthesised and investigated as potential human monoamine oxidase (hMAO) inhibitors in vitro as well as ex vivo in rat cortex synaptosomes by means of evaluation of 3,4-dihydroxyphenylacetic acid/dopamine (DOPAC/DA) ratio and lactate dehydrogenase (LDH) activity. Most of these compounds possessed high selectivity for the MAO-B isoform and a discrete antioxidant and chelating potential. Molecular docking studies of all the compounds underscored potential binding site interactions suitable for MAO inhibition activity, and suggested structural requirements to further improve the activity of this scaffold by chemical modification of the aryl substituents. Starting from this heterocyclic nucleus, novel lead compounds for the treatment of neurodegenerative disease could be developed.

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Section: Introductionmentioning

confidence: 99%

Benzo[b]tiophen-3-ol derivatives as effective inhibitors of human monoamine oxidase: design, synthesis, and biological activity

Guglielmi

Secci

Petzer

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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ChemInform Abstract: Facile Synthesis of 2‐Substituted Benzo[b]thiophen‐3‐ols in Water.

et al. 2013

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Tandem S_N2 Nucleophilic Substitution/Phospho-Dieckmann Reaction: One-Step Synthesis of 2-Phosphonyl-3-hydroxybenzo[b]thiophenes

Li,

Shen,

Shen

et al. 2023

J. Org. Chem.

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A novel and efficient tandem S N 2 nucleophilic substitution/Dieckmann condensation reaction of α-iodomethyl phosphine oxide with methyl thiosalicylate derivatives has been developed by using NaOH as a base, which enables the expeditious synthesis of 2-phosphonyl-3-hydroxybenzo[b]thiophene derivatives in moderate to high yields under simple conditions. This research provides not only a convenient method for the functionalization of benzo[b]thiophenes at the 2-position and 3-position but also new organophosphorus molecules. Furthermore, several new phosphonyl-substituted benzo[b]thiophenes were obtained from the resultant 2-phosphonyl-3-hydroxybenzo[b]thiophenes.

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Facile Synthesis of 2-Substituted Benzo[b]thiophen-3-ols in Water

Cited by 6 publications

References 30 publications

Benzo[b]tiophen-3-ol derivatives as effective inhibitors of human monoamine oxidase: design, synthesis, and biological activity

Benzo[b]tiophen-3-ol derivatives as effective inhibitors of human monoamine oxidase: design, synthesis, and biological activity

ChemInform Abstract: Facile Synthesis of 2‐Substituted Benzo[b]thiophen‐3‐ols in Water.

Tandem S_N2 Nucleophilic Substitution/Phospho-Dieckmann Reaction: One-Step Synthesis of 2-Phosphonyl-3-hydroxybenzo[b]thiophenes

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Facile Synthesis of 2-Substituted Benzo[b]thiophen-3-ols in Water

Cited by 6 publications

References 30 publications

Benzo[b]tiophen-3-ol derivatives as effective inhibitors of human monoamine oxidase: design, synthesis, and biological activity

Benzo[b]tiophen-3-ol derivatives as effective inhibitors of human monoamine oxidase: design, synthesis, and biological activity

ChemInform Abstract: Facile Synthesis of 2‐Substituted Benzo[b]thiophen‐3‐ols in Water.

Tandem SN2 Nucleophilic Substitution/Phospho-Dieckmann Reaction: One-Step Synthesis of 2-Phosphonyl-3-hydroxybenzo[b]thiophenes

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Tandem S_N2 Nucleophilic Substitution/Phospho-Dieckmann Reaction: One-Step Synthesis of 2-Phosphonyl-3-hydroxybenzo[b]thiophenes