Synthesis and biological evaluation of novel <i>N</i>‐aryl‐<i>ω</i>‐(benzoazol‐2‐yl)‐sulfanylalkanamides as dual inhibitors of α‐glucosidase and protein tyrosine phosphatase 1B

Wang, Meiyan; Cheng, Xian-Chao; Chen, Xiu-Bo; Yu, Lupeng; Zang, Lanlan; Duan, Yuqing; Chen, Mingzhu; Yu, Peng; Hua, Sun; Wang, Run‐Ling

doi:10.1111/cbdd.13331

Cited by 16 publications

(6 citation statements)

References 48 publications

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“…Compound 54 showed potent activity with IC 50 : 10.96 μM as compared to standard acarbose 51.32 μM and docking study generated six H-bonds with the highest interactions with the PTP1B catalytic site being those with residues Phe182, Cys215, Ser216, and Arg221, as well as those with important residues His112, Gln182, Glu277, and Arg442 and 13.46 μM as compared to standard ursolic acid 18.22 μM for PTP1B inhibition. [61] Gong Z et al reported α-Glucosidase Inhibitory activity of produced and screened benzothiazole triazole derivatives was examined. Compound 55 exhibits a marked increase in inhibitory action upon the introduction of the electron-withdrawing group chlorine into the benzothiazole ring with IC 50 : 20.7 μM as compared to standard acarbose with IC 50 :817.38 μM.…”

Section: Pharmacological Characteristics Of Benzothiazole Analoguesmentioning

confidence: 99%

Recent Studies of Nitrogen and Sulfur Containing Heterocyclic Analogues as Novel Antidiabetic Agents: A Review

Gharge,

Alegaon

2024

Chemistry & Biodiversity

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The prevalence of diabetes mellitus is on the rise, which demands for the identification of novel antidiabetic drugs. There is a need for safer and more effective alternatives because the therapy methods now available to manage diabetes have limits. Due to their diverse pharmacological characteristics, heterocyclic molecules with nitrogen and Sulfur atoms have become intriguing candidates in medicinal chemistry. These substances have a wide variety of structures that can be customized to target different pathways associated with diabetes and can affect important biological targets involved in glucose homeostasis. This review provides a thorough summary of the most recent studies on heterocyclic analogues of nitrogen and Sulfur as prospective antidiabetic agents. This review examines the variety of their structural forms, their methods of action, and assesses the results of preclinical and clinical investigations on their effectiveness and safety. Additionally, further optimization and development of innovative antidiabetic medications are highlighted, as well as the difficulties and prospects for the future in utilizing the therapeutic potential of these analogues. This study seeks to stimulate additional investigation and cooperation between researchers and medicinal chemists, promoting improvements in the creation of efficient and secure antidiabetic medicines to fulfil the needs in the management of diabetes.

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Section: Pharmacological Characteristics Of Benzothiazole Analoguesmentioning

confidence: 99%

Recent Studies of Nitrogen and Sulfur Containing Heterocyclic Analogues as Novel Antidiabetic Agents: A Review

Gharge,

Alegaon

2024

Chemistry & Biodiversity

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“…Wang and co-workers (2018) investigated a library of N-Arylω-(Benzoazol-2-yl)-sulfanylalkanamides for their effect on the SHP2 inhibition ( Figure 28). All the compounds (91-92) were found to be inactive against SHP2 (IC 50 > 100 µM) (Wang, Cheng, et al, 2018…”

Section: Sulfanylalkanamidesmentioning

confidence: 99%

Emerging chemical scaffolds with potential SHP2 phosphatase inhibitory capabilities – A comprehensive review

Tripathi

Ayyannan

2020

Chem Biol Drug Des

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The drug discovery panorama is cluttered with promising therapeutic targets that have been deserted because of inadequate authentication and screening failures. Molecular targets formerly tagged as "undruggable" are nowadays being more cautiously cross-examined, and whilst they stay intriguing, numerous targets are emerging more accessible. Protein tyrosine phosphatases (PTPs) excellently exemplifies a class of molecular targets that have transpired as druggable, with several small molecules and antibodies recently turned available for further development. In this respect, SHP2, a PTP, has emerged as one of the potential targets in the current pharmacological research, particularly for cancer, due to its critical role in various signalling pathways. Recently, few molecules with excellent potency have entered clinical trials, but none could reach the clinic. Consequently, search for novel, non-toxic, and specific SHP2 inhibitors are on purview. In this review, general aspects of SHP2 including its structure and mechanistic role in carcinogenesis have been presented. It also sheds light on the development of novel molecular architectures belonging to diverse chemical classes that have been proposed as SHP2-specific inhibitors along with their structure-activity relationships (SARs), stemming from chemical, mechanism-based and computer-aided studies reported since January 2015 to July 2020 (excluding patents), focusing on their potency and selectivity. The encyclopedic facts and discussions presented herein will hopefully facilitate researchers to design new ligands with better efficacy and selectivity against SHP2.

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“…Thus inhibiting the α-glucosidase would obviously control the postprandial hyperglycemia. α-Glucosidase inhibitors can block the hydrolysis of 1, 4-glycosidic bonds and delay the hydrolysis of carbohydrates into glucose, resulting in the effective reduction of postprandial blood sugar ( Al-Salahi, et al, 2018 ; Qamar, et al, 2018 ; Shah, et al, 2018 ; Wang, et al, 2018 ). Up to now, a great number of naturally occurring and synthetic α-glucosidase inhibitors have been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of 5-Fluoro-2-Oxindole Derivatives as Potential α-Glucosidase Inhibitors

Lin

Liang

et al. 2022

Front. Chem.

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α-Glucosidase inhibitors are known to prevent the digestion of carbohydrates and reduce the impact of carbohydrates on blood glucose. To develop novel α-glucosidase inhibitors, a series of 5-fluoro-2-oxindole derivatives (3a ∼ 3v) were synthesized, and their α-glucosidase inhibitory activities were investigated. Biological assessment results showed that most synthesized compounds presented potential inhibition on α-glucosidase. Among them, compounds 3d, 3f, and 3i exhibited much better inhibitory activity with IC50 values of 49.89 ± 1.16 μM, 35.83 ± 0.98 μM, and 56.87 ± 0.42 μM, respectively, which were about 10 ∼ 15 folds higher than acarbose (IC50 = 569.43 ± 43.72 μM). A kinetic mechanism study revealed that compounds 3d, 3f, and 3i inhibited the α-glucosidase in a reversible and mixed manner. Molecular docking was carried out to simulate the affinity between the compound and α-glucosidase.

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Synthesis and biological evaluation of novel N‐aryl‐ω‐(benzoazol‐2‐yl)‐sulfanylalkanamides as dual inhibitors of α‐glucosidase and protein tyrosine phosphatase 1B

Cited by 16 publications

References 48 publications

Recent Studies of Nitrogen and Sulfur Containing Heterocyclic Analogues as Novel Antidiabetic Agents: A Review

Recent Studies of Nitrogen and Sulfur Containing Heterocyclic Analogues as Novel Antidiabetic Agents: A Review

Emerging chemical scaffolds with potential SHP2 phosphatase inhibitory capabilities – A comprehensive review

Synthesis and Biological Evaluation of 5-Fluoro-2-Oxindole Derivatives as Potential α-Glucosidase Inhibitors

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