Design and synthesis of 2,6-di(substituted phenyl)thiazolo[3,2-b]-1,2,4-triazoles as α-glucosidase and α-amylase inhibitors, co-relative Pharmacokinetics and 3D QSAR and risk analysis

Channar, Pervaiz Ali; Saeed, Aamer; Larik, Fayaz Ali; Rashid, Sajid; Iqbal, Qaiser; Rozi, Maryam; Younis, Saima; Mahar, Jamaluddin

doi:10.1016/j.biopha.2017.07.139

Cited by 35 publications

(13 citation statements)

References 73 publications

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“…Urease has assorted capacities and its inhibition has received exceptional consideration in the course of recent years and numerous urease inhibitors have been described. Among these are hydroxamic corrosive subordinates [ 17 ], hydroxyurea [ 18 ], hydroxamic acids [ 19 ], phosphorodiamidates, imidazoles, for example, rabeprazole, lansoprazole, omeprazole, quinines, thiol derivatives, and phenols, Schiff base and thiourea derivatives [ 20 ]. Sulfonamides constitute an important class of organic compounds that possess a broad spectrum of biological activities such as antibacterial, high-ceiling diuretic, hypoglycemic, antithyroid, anti-inflammatory and antiglaucoma effects [ 21 , 22 , 23 , 24 , 25 , 26 , 27 ].…”

Section: Introductionmentioning

confidence: 99%

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

et al. 2017

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Sulfonamide derivatives serve as an important building blocks in the drug design discovery and development (4D) process. Ciprofloxacin-, sulfadiazine- and amantadine-based sulfonamides were synthesized as potent inhibitors of jack bean urease and free radical scavengers. Molecular diversity was explored and electronic factors were also examined. All 24 synthesized compounds exhibited excellent potential against urease enzyme. Compound 3e (IC50 = 0.081 ± 0.003 µM), 6a (IC50 = 0.0022 ± 0.0002 µM), 9e (IC50 = 0.0250 ± 0.0007 µM) and 12d (IC50 = 0.0266 ± 0.0021 µM) were found to be the lead compounds compared to standard (thiourea, IC50 = 17.814 ± 0.096 µM). Molecular docking studies were performed to delineate the binding affinity of the molecules and a kinetic mechanism of enzyme inhibition was propounded. Compounds 3e, 6a and 12d exhibited a mixed type of inhibition, while derivative 9e revealed a non-competitive mode of inhibition. Compounds 12a, 12b, 12d, 12e and 12f showed excellent radical scavenging potency in comparison to the reference drug vitamin C.

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Section: Introductionmentioning

confidence: 99%

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

et al. 2017

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“…Derivative having R 1 =3‐Methyl and R 2 =3‐Nitro substituent (IC 50 =1.1 μM) was found to be the most active compound. Electron withdrawing groups enhanced the activity due to charge separation [73] …”

Section: Synthetic Developments On N‐heterocyclic Compoundsmentioning

confidence: 99%

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

et al. 2022

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In nature, N‐heterocyclic compounds and their derivatives are abundant. They serve as the building blocks of many biological entities, such as enzymes, alkaloids, hormones, antibiotics, and vitamins. The treatment of diabetes is one of the major applications of heterocyclic compounds. Natural as well as synthetic, both types of heterocyclic compounds show anti‐diabetic activity. There is a plethora of literature on the hyper/hypoglycaemic activity of natural compounds. This review discusses the synthesis methods, yields of the reactions and Inhibitory concentration (IC50) values of all the synthesized derivatives via different assays such as 3,5‐dinitrosalicylic acid (DNS) or starch assays. IC50 values of all the derivatives have been compared with those of standard acarbose. Structure activity relationship of most potential compounds with α‐amylase enzyme is established to show the type of interactions between them. Molecular docking studies show the type of interaction between compounds and enzyme.

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“…Glucosidase inhibitors are highly promising in the treatment of various diseases such as diabetes, viral infections and cancer metastasis, as well as being a very effective tool for understanding the mechanism of action of glucosidases [21]. Therefore, αamylase has been the target enzyme for the design of drug molecules suitable for the treatment of diabetes, obesity, and hyperglycemia.…”

Section: Alpha Amylase Inhibition Resultsmentioning

confidence: 99%

Cytotoxicity and anti-small cell lung cancer potential of 3-methoxy-5-nitrosalicylaldehyde: an analog for treatment of diabetes mellitus with considerable binding affinity to α-amylase enzyme

2021

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IntroductionAlpha-amylase inhibitors are present in plants and are thought to be produced by plants to strengthen their defenses against predators. It contains plant components, polyphenolic compounds and glycoproteins with enzymatic inhibitory activity.Material and methodsThe molecular docking investigation was accomplished as a versatile method for the evaluation of the biological activities of 3-Methoxy-5-nitrosalicylaldehyde in the presence of alpha amylase. MTT test was used on normal (HUVEC) and small cell lung cancer (SBC-3, DMS273, and DMS114) cell lines.ResultsIn this study, inhibition result of metabolic enzyme was obtained IC50: 95.14 µM. The compound exhibited a considerable binding affinity to the enzyme with a docking score of -7.676 kcal/mol. The results of the molecular docking revealed that 3-Methoxy-5-nitrosalicylaldehyde is able to construct hydrophobic contacts with crucial residues of the catalytic domain of the enzyme. According to these findings, the compound has the potential to be an inhibitor for alpha amylase. 3-Methoxy-5-Nitrosalicylaldehyde had high cell death and anti-small cell lung cancer effects against SBC-3, DMS273, and DMS114 cell lines. Among the above cell lines, the best result of anti-small cell lung cancer properties of molecule was gained in the cell line of DMS273.ConclusionsThe results of this study indicated the excellent anti-small cell lung cancer potentials of 3-Methoxy-5-Nitrosalicylaldehyde in the in vitro condition. After confirming the above results in the clinical trial researches, this formulation may be administrated for the treatment of several types of small cell lung cancer in humans.

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Design and synthesis of 2,6-di(substituted phenyl)thiazolo[3,2-b]-1,2,4-triazoles as α-glucosidase and α-amylase inhibitors, co-relative Pharmacokinetics and 3D QSAR and risk analysis

Cited by 35 publications

References 73 publications

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

Sulfonamide-Linked Ciprofloxacin, Sulfadiazine and Amantadine Derivatives as a Novel Class of Inhibitors of Jack Bean Urease; Synthesis, Kinetic Mechanism and Molecular Docking

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

Cytotoxicity and anti-small cell lung cancer potential of 3-methoxy-5-nitrosalicylaldehyde: an analog for treatment of diabetes mellitus with considerable binding affinity to α-amylase enzyme

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