Discovery of core-structurally novel PTP1B inhibitors with specific selectivity containing oxindole-fused spirotetrahydrofurochroman by one-pot reaction

Shen, Dong; Lei, Yubing; Jia, Shi-Kun; Gao, Lixin; Li, Jia; Zhu, Tong; Liu, Shunying; Hu, Wenhao

doi:10.1016/j.bmcl.2016.11.055

Cited by 14 publications

(4 citation statements)

References 19 publications

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“…In general, the addition of ‐OMe, ‐Me, ‐Br, and ‐Cl to sites P2 and P3 increases the activity against PTP1B while compounds without substituents at both P2 and P3 did not affect PTP1B, despite having a γ‐lactam ring, which proves substitutes on‐site P2 and P3 are considerably essential. Molecular docking showed 57 bound to PTP1B's active pocket (Dong et al, 2017).…”

Section: Synthetic Ptp1b Inhibitorsmentioning

confidence: 99%

A comprehensive review on the research progress of PTP1B inhibitors as antidiabetics

Agrawal,

Dhakrey,

Pathak

2023

Chem Biol Drug Des

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Diabetes mellitus (DM) is a serious global health concern affecting over 500 million people. To put it simply, it is one of the most dangerous metabolic illnesses. Insulin resistance is the root cause of 90% of all instances of diabetes, all of which are classified as Type 2 DM. Untreated, it poses a hazard to civilization since it can lead to terrifying consequences and even death. Oral hypoglycemic medicines presently available act in a variety of ways, targeting various organs and pathways. The use of protein tyrosine phosphatase 1B (PTP1B) inhibitors, on the contrary, is a novel and effective method of controlling type 2 diabetes. PTP1B is a negative insulin signaling pathway regulator; hence, inhibiting PTP1B increases insulin sensitivity, glucose absorption, and energy expenditure. PTP1B inhibitors also restore leptin signaling and are considered a potential obesity target. In this review, we have compiled a summary of the most recent advances in synthetic PTP1B inhibitors from 2015 to 2022 which have scope to be developed as clinical antidiabetic drugs.

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Section: Synthetic Ptp1b Inhibitorsmentioning

confidence: 99%

A comprehensive review on the research progress of PTP1B inhibitors as antidiabetics

Agrawal,

Dhakrey,

Pathak

2023

Chem Biol Drug Des

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“…Chiral spirooxindoles are the structural scaffolds of many well-known pharmaceutically and medicinally relevant compounds and exhibit a wild range of biological activities such as antitumor, antimicrobial, antifungal, and anti-inflammatory activities (Figure ). Consequently, the construction of the spirooxindole scaffold, especially with easily available starting materials, has attracted a considerable amount of attention. Although various organocatalytic asymmetric cycloadditions and metal/ligand complex-catalyzed asymmetric cycloadditions have been applied to afford the optically active spirooxindoles, the diethyl phosphite-mediated cyclization strategy has not been utilized to access spirocyclic oxindoles.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective Synthesis of Tetrabenzohydrofuran Spirooxindoles via Diethyl Phosphite-Mediated Coupling of Isatins with o-Quinone Methides

et al. 2021

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Diethyl phosphite-initiated coupling of isatins with o-quinone methides (o-QMs) is reported. This reaction involves a cascade transformation initiated by base-promoted addition of phosphite to isatins, followed by [1,2]-phospha-Brook rearrangement. This generates α-phosphonyloxy enolates that are subsequently intercepted by o-QMs and finally intramolecular ring closure. This protocol was used to diastereoselectively synthesize a range of trans-tetrabenzohydrofuran spirooxindoles in moderate to good yields with moderate to excellent diastereoselectivities.

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“…In view of the medicinal relevance of furo[3,2- c ]benzopyrans and tetrahydrofuryl spirooxindoles, the integration of these two interesting frameworks would produce structurally complex and diverse new molecules, which will not only inherit the structures of both scaffolds but also provide a good opportunity to discover new bioactivities after bioassays. In this context, recently new compounds comprising a spiro-furo[3,2- c ]benzopyranoxindole core have been found to act as potent inhibitors of protein tyrosine phosphatase 1B (PTP1B) …”

Section: Introductionmentioning

confidence: 99%

“…Although valuable pharmaceutical activities have been connected to spiro-furo[3,2- c ]benzopyranoxindoles, approaches for this interesting hybrid scaffold remain rather limited. To the best of our knowledge, there is only one strategy that can be used for the construction of them via a tandem reaction sequence . This method involves a three-component [3 + 2] cycloaddition followed by cyclization through an intramolecular Michael addition.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective Construction of Spiro-furo[3,2-c]benzopyranoxindoles through a Cu(OTf)₂/AcOH Cooperative Promoted Bicyclization Reaction

Zhang

et al. 2018

J. Org. Chem.

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We disclose herein a highly diastereoselective approach for the Cu(OTf)2/AcOH cooperative promoted bicyclization reaction of 3-cinnamyl-3-hydroxy-2-oxindoles and ortho-quinonemethides (o-QMs) generated in situ from salicylaldehydes for the synthesis of spiro-furo[3,2-c]benzopyranoxindoles. The reaction has the advantages of readily available starting materials, simple operation, and high bond-forming efficiency, which not only provides an efficient access to spiro-furo[3,2-c]benzopyranoxindoles but also enriches the research contents of o-QMs-involved reactions. The synthetic applications of the products such as amide reduction are also demonstrated.

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Discovery of core-structurally novel PTP1B inhibitors with specific selectivity containing oxindole-fused spirotetrahydrofurochroman by one-pot reaction

Cited by 14 publications

References 19 publications

A comprehensive review on the research progress of PTP1B inhibitors as antidiabetics

A comprehensive review on the research progress of PTP1B inhibitors as antidiabetics

Diastereoselective Synthesis of Tetrabenzohydrofuran Spirooxindoles via Diethyl Phosphite-Mediated Coupling of Isatins with o-Quinone Methides

Diastereoselective Construction of Spiro-furo[3,2-c]benzopyranoxindoles through a Cu(OTf)₂/AcOH Cooperative Promoted Bicyclization Reaction

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Discovery of core-structurally novel PTP1B inhibitors with specific selectivity containing oxindole-fused spirotetrahydrofurochroman by one-pot reaction

Cited by 14 publications

References 19 publications

A comprehensive review on the research progress of PTP1B inhibitors as antidiabetics

A comprehensive review on the research progress of PTP1B inhibitors as antidiabetics

Diastereoselective Synthesis of Tetrabenzohydrofuran Spirooxindoles via Diethyl Phosphite-Mediated Coupling of Isatins with o-Quinone Methides

Diastereoselective Construction of Spiro-furo[3,2-c]benzopyranoxindoles through a Cu(OTf)2/AcOH Cooperative Promoted Bicyclization Reaction

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Diastereoselective Construction of Spiro-furo[3,2-c]benzopyranoxindoles through a Cu(OTf)₂/AcOH Cooperative Promoted Bicyclization Reaction