Dataset Information

Synthesis of 2-Aryl-4H-thiochromen-4-one Derivatives via a Cross-Coupling Reaction.

ABSTRACT: A concise and efficient cross-coupling synthetic strategy has been developed to construct 2-aryl-4H-thiochromen-4-one derivatives from 2-sulfinyl-thiochromones and arylboronic acids. This reaction proceeds via a catalyst system of Lewis acid and palladium(II) combined with XPhos as an optimal ligand in moderate to good yields. Besides, this flexible methodology provides a wide scope for the synthesis of different functionally substituted thiochromone scaffolds and can be further exploited to construct diverse thioflavone libraries for pharmaceutical research.

SUBMITTER: Li P

PROVIDER: S-EPMC8190924 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Synthesis of 2-Aryl-4H-thiochromen-4-one Derivatives via a Cross-Coupling Reaction.

Li Peng P Li Shengnan S Li Gang G Huang Haihong H

ACS omega 20210521 22

A concise and efficient cross-coupling synthetic strategy has been developed to construct 2-aryl-4H-thiochromen-4-one derivatives from 2-sulfinyl-thiochromones and arylboronic acids. This reaction proceeds via a catalyst system of Lewis acid and palladium(II) combined with XPhos as an optimal ligand in moderate to good yields. Besides, this flexible methodology provides a wide scope for the synthesis of different functionally substituted thiochromone scaffolds and can be further ex ...[more]

PMID: 34124488

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Project description:Pyrazolo[3,4-b]pyridine scaffolds have been heavily exploited in the development of nitrogen-containing heterocycles with numerous therapeutic applications in the field of medicinal and pharmaceutical chemistry. The present work describes the synthesis of eighteen biaryl pyrazolo[3,4-b]pyridine ester (6a-i) and hydrazide (7a-i) derivatives via the Suzuki cross-coupling reaction. These derivatives were subsequently screened for their therapeutic potential to inhibit the diabetic α-amylase enzyme, which is a key facet of the development of anti-diabetic agents. Initially, the ethyl 4-(4-bromophenyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylate 4 was synthesized through a modified Doebner method under solvent-free conditions, providing an intermediate for further derivatization with a 60% yield. This intermediate 4 was subjected to Suzuki cross-coupling, reacting with electronically diverse aryl boronic acids to obtain the corresponding pyrazolo[3,4-b]pyridine ester derivatives (6a-i). Following this, the biaryl ester derivatives (6a-i) were converted into hydrazide derivatives (7a-i) through a straightforward reaction with hydrazine monohydrate and were characterized using 1H-NMR, 13C-NMR, and LC-MS spectroscopic techniques. These derivatives were screened for their α-amylase inhibitory chemotherapeutic efficacy, and most of the biaryl ester and hydrazide derivatives demonstrated promising amylase inhibition. In the (6a-i) series, the compounds 6b, 6c, 6h, and 6g exhibited excellent inhibition, with almost similar IC50 values of 5.14, 5.15, 5.56, and 5.20 μM, respectively. Similarly, in the series (7a-i), the derivatives 7a, 7b, 7c, 7d, 7f, 7g, and 7h displayed excellent anti-diabetic activities of 5.21, 5.18, 5.17, 5.12, 5.10, 5.16, and 5.19 μM, respectively. These in vitro results were compared with the reference drug acarbose (IC50 = 200.1 ± 0.15 μM), demonstrating better anti-diabetic inhibitory activity in comparison to the reference drug. The in silico molecular docking study results were consistent with the experimental biological findings, thereby supporting the in vitro pharmaceutical efficacy of the synthesized derivatives.

Dataset Information

Synthesis of 2-Aryl-4H-thiochromen-4-one Derivatives via a Cross-Coupling Reaction.

Publications

Synthesis of 2-Aryl-4<i>H</i>-thiochromen-4-one Derivatives <i>via</i> a Cross-Coupling Reaction.

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