Comparative α-glucosidase and α-amylase inhibition studies of rhodanine–pyrazole conjugates and their simple rhodanine analogues

Singh, Pushpinder; Mothilal, Serisha; Kerru, Nagaraju; Singh‐Pillay, Ashona; Gummidi, Lalitha; Erukainure, Ochuko L.; Islam, Md. Shahidul

doi:10.1007/s00044-018-2272-z

Cited by 36 publications

(13 citation statements)

References 42 publications

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“…[8,9] Rhodanine derivatives displayed a wide range of biological activities such as antimicrobial, [10,11] antitubercular, [12] anticancer, [13] antiviral, [14] anti-inflammatory, [15] antimalarial, [16] antioxidant [17] and acetylcholinesterase inhibitor [18] activities. They have emerged as promising motif in antidiabetic drug discovery program and as reported in the literature (Figure 1), Rhodanine derivative 1 showed PPARγ binding activity, [19] 2, 3 as potent α-glucosidase inhibitors, [20,21] and 4displayed aldose reductase inhibitory activity. [22] Similarly, Rhodanine-3-acetic acid derivatives possesses wide range of biological activity [8] and its derivative, Epalrestat (5) is used for the treatment of various diabetic complications.…”

Section: Introductionmentioning

confidence: 99%

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

Kumar

Ramu

Shirahatti³

et al. 2021

ChemistrySelect

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In our effort to identify potent fluorinated small molecules as antidiabetic compounds, a novel fluorinated series of 2-chloro-6-(trifluoromethyl)benzyloxy arylidene derived Rhodanine and Rhodanine-acetic acid derivatives were synthesized and screened for α-glucosidase and α-amylase inhibitory activity. Newly synthesized compounds were characterized by 1 HNMR, 13 C NMR, and LCMS spectral data. Among the tested compounds, (Z)-5-(4-(2-chloro-6-(trifluoromethyl)benzyloxy) benzylidene)-2-thioxothiazolidin-4-one(5 a) and 2-((Z)-5-(4-(2chloro-6-(trifluoromethyl)benzyloxy)benzylidene)-4-oxo-2-thioxothiazoli-din-3-yl)acetic acid(6 a) emerged as most promising α-glucosidase inhibitors with IC 50 values 4.76 � 0.64 μM and 4.91 � 0.45 μM, respectively. Further, the kinetic inhibition experiments against yeast α-glucosidase for compounds 5 a and 6 a indicated that these are competitive inhibitors with inhibitory constant (Ki) 0.54 μg and 1.15 μg respectively.Molecular docking studies on α-glucosidase was performed by homology modelingfor the most potent compounds 5 a and 6 a to understand the putative binding mode. The study revealed substantial binding of the compounds to the active site of α-glucosidase, indicating that the position of the substituent plays a key role in its inhibitory potential.

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Section: Introductionmentioning

confidence: 99%

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

Kumar

Ramu

Shirahatti³

et al. 2021

ChemistrySelect

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“…The figure (1-3) indicated that all tested compounds showed excellent inhibitory activity with high absorbance values. Compounds (1, 3) were found to be the most potent than standard reference drug metformin HCl in all concentration .Also compound (1) was showed stronger activity than compound (3) at concentration (10,15,20) µg/3ml. finally, the present study exhibited a new class of α-amylase inhibitors based on rhodanine derivatives compounds.…”

Section: In Vitro α-Amylase Inhibitory Activitymentioning

confidence: 89%

“…The α-amylase inhibitory activity of the synthesised compounds were determined using revised method (14) in which 250 μL of each compound, or Metformin .HCl, dissolved in ethanol to obtain different concentrations (5,10,15,20,30 and 40 μg/mL), was mixed with 500 μL of aamylase (2 U/mL) in phosphate buffer (100 mM, pH 6.8) and incubated at 37 °C for 10 min. Thereafter, 50 μL of 1% starch, dissolved inthe same buffer, was added to the mixture and the samples were incubated again at 37 °C.…”

Section: Determination Of α-Amylase Inhibitory Activitymentioning

confidence: 99%

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Rhodanine- 3- acetic acid derivatives as a new class of potent α-amylase inhibitors: synthesis and molecular docking study

2020

JCBSC

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Rhodanines are accepted as advantaged heterocycles in medicinal chemistry. Several therapeutic anti-diabetic drugs, were prepared using rhodanine nucleus. Thus, some rhodanine-3-acetic acid and its derivatives 1-3 were prepared. The compounds were structurally characterized based on 1 HNMR and IR data, and there in vitro α-amylase inhibitory activity was evaluated using fungal diastase αamylase enzyme. The results indicated that the novel compounds rhodanine-3-acetic acid and its derivatives (1-3) were potent α-amylase inhibitors because of its higher IC50 value compared with metformin .HCl as standard reference drug.

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“…Among azoles, pyrazole and isoxazole hold special position as emerging nitrogen heterocycles in the domain of chemotherapeutics and pharmaceuticals. Additionally, established a vast scope in terms of biological activities such as antiproliferative, anti-inflammatory, antioxidant, anticancer, antileishmanial, antimicrobial, antibacterial, antiarrhythmic, anti-convulsant, α-glucosidase inhibitor, antipsychotic, etc [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Synthetic methodology and applications for symmetrical 1,3,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles are ubiquitous in literature and easy to execute.…”

Section: Introductionmentioning

confidence: 99%

Synthetic strategies for 1,4,5/4,5‐substituted azoles: A perspective review

Kamal

Kumar

2022

Journal of Heterocyclic Chem

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Azole nucleus represents an important class of biologically active compounds that are gaining more attention in the field of medicinal chemistry due to large number of structure diversity. Among azoles, pyrazoles, and isoxazoles fivemembered nitrogen containing heterocyclic compounds are associated wide range of biological activities such as anticancer, antimicrobial, anti-inflammatory, antioxidant, etc. Some of azole derivatives (e.g., 1,4,5-trisubstituted pyrazoles, 4,5-disubstituted isoxazoles, and 4,5-disubstituted-1H-pyrazoles) are still unexplored in literature, these unexplored azoles have fascinated the consideration of many researchers to study their framework synthetically and biologically. This present review is an attempt to update and understand the chemistry of unexplored pyrazoles and isoxazoles along with their medicinal importance. This article would definitely help the researchers to bring further enhancement in the synthesis of biologically active pyrazoles and isoxazoles.

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Comparative α-glucosidase and α-amylase inhibition studies of rhodanine–pyrazole conjugates and their simple rhodanine analogues

Cited by 36 publications

References 42 publications

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

α‐Glucosidase, α‐Amylase Inhibition, Kinetics and Docking Studies of Novel (2‐Chloro‐6‐(trifluoromethyl)benzyloxy)arylidene) Based Rhodanine and Rhodanine Acetic Acid Derivatives

Rhodanine- 3- acetic acid derivatives as a new class of potent α-amylase inhibitors: synthesis and molecular docking study

Synthetic strategies for 1,4,5/4,5‐substituted azoles: A perspective review

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