Synthesis of 1,2,3,triazole modified analogues of hydrochlorothiazide via click chemistry approach and in-vitro α-glucosidase enzyme inhibition studies

Siddiqui, Hamid Latif; Baheej, M A A; Ullah, Saeed; Rizvi, Fazila; Iqbal, Shazia; Haniffa, Haroon M.; Wahab, Atia‐tul; Choudhary, Muhammad Iqbal

doi:10.1007/s11030-021-10314-3

Cited by 7 publications

(3 citation statements)

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“…It has been discovered that limiting the effect of dietary carbohydrates on blood sugar is critical. 5,6 Meldrum's acid, that is, 2,2-dimethyl-1,3-dioxan-4,6-dione (R 1 = Me, R 2 , R 3 = H), was prepared in 1908 by Andrew Norman Meldrum; however, the exact structure was revealed in 1948 by Davidson and Benhard (Scheme 1). 7 Meldrum's acid derivatives are bench-stable, easily accessible compounds that act as crucial organic building blocks, which are fundamental components in organic synthesis and flourishing applications in the synthesis of natural products and multicomponent reactions (MCRs).…”

Section: Introductionmentioning

confidence: 99%

“…By delaying the digestion of carbohydrates, α-GI limits the rate of glucose absorption and avoids the progression of the impaired glucose tolerance factor (GTF) to T2DM. It has been discovered that limiting the effect of dietary carbohydrates on blood sugar is critical. , …”

Section: Introductionmentioning

confidence: 99%

“…It has been discovered that limiting the effect of dietary carbohydrates on blood sugar is critical. 5 , 6 …”

Section: Introductionmentioning

confidence: 99%

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Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

et al. 2023

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A series of novel alkyl derivatives (2−5a,b) and 1H-1,2,3-triazole analogues (7a−k) of Meldrum's acid were synthesized in a highly effective way by using "click" chemistry and screened for in vitro α-glucosidase inhibitory activity to examine their antidiabetic potential. 1 H NMR, 13 C-NMR, and highresolution electrospray ionization mass spectra (HR-ESI-MS) were used to analyze each of the newly synthesized compounds. Interestingly, these compounds demonstrated high to moderate αglucosidase inhibitory potency having an IC 50 range of 4.63−80.21 μM. Among these derivatives, compound 7i showed extraordinary inhibitory activity and was discovered to be several times more potent than the parent compound Meldrum (1) and the standard drug acarbose. Later, molecular docking was performed to understand the binding mode and the binding strength of all the compounds with the target enzyme, which revealed that all compounds are well fitted in the active site of α-glucosidase. To further ascertain the structure of compounds, suitable X-ray single crystals of compounds 5a, 7a, and 7h were developed and studied. The current investigation has shown that combining 1H-1,2,3-triazole with the Meldrum moiety is beneficial. Furthermore, this is the first time that the aforementioned activity of these compounds has been reported.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

et al. 2023

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Recent Developments in 1,2,3‐Triazole Based α‐Glucosidase Inhibitors: Design Strategies, Structure‐Activity Relationship and Mechanistic Insights

Singh,

Sharma

et al. 2024

Chemistry & Biodiversity

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Diabetes mellitus is a chronic and most prevalent metabolic disorder affecting 422 million the people worldwide and causing life‐threatening associated conditions including disorders of kidney, heart, and nervous system as well as leg amputation and retinopathy. Steadily rising cases from the last few decades suggest the failure of currently available drugs in containment of this disease. α‐Glucosidase is a potential target for effectively tackling this disease and attracting significant interest from medicinal chemists around the globe. Besides having a set of side effects, currently available α‐glucosidase inhibitors (carbohydrate mimics) offer better tolerability, safety, and synergistic pharmacological outcomes with other antidiabetic drugs therefore medicinal chemists have working extensively over last three decades for developing alternative α‐glucosidase inhibitors. The 1,2,3‐Triazole nucleus is energetically used by various research groups around the globe for the development of α‐glucosidase inhibitors posing it as an optimum scaffold in the field of antidiabetic drug development. This review is a systematic analysis of α‐glucosidase inhibitors developed by employing 1,2,3‐triazole scaffold with special focus on design strategies, structure‐activity relationships, and mechanism of inhibitory effect. This article will act as lantern for medicinal chemists in developing of potent, safer, and effective α‐glucosidase inhibitors with desired properties and improved therapeutic efficacy.

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Mesoporous epoxidized soybean oil-supported copper-based magnetic nanocatalyst and amberlite-supported azide as a green and efficient catalytic system for 1,2,3-triazole synthesis

et al. 2022

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Synthesis of 1,2,3,triazole modified analogues of hydrochlorothiazide via click chemistry approach and in-vitro α-glucosidase enzyme inhibition studies

Cited by 7 publications

References 44 publications

Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

Recent Developments in 1,2,3‐Triazole Based α‐Glucosidase Inhibitors: Design Strategies, Structure‐Activity Relationship and Mechanistic Insights

Mesoporous epoxidized soybean oil-supported copper-based magnetic nanocatalyst and amberlite-supported azide as a green and efficient catalytic system for 1,2,3-triazole synthesis

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