Synthesis, α-amylase inhibition and molecular docking study of bisindolylmethane sulfonamide derivatives

Taha, Muhammad; Noreen, Tayyaba; Imran, Syahrul; Nawaz, Fasial; Chigurupati, Sridevi; Selvaraj, Manikandan; Ismail, Nor Hadiani; Kumar, Ashok; Mosaddik, Ashik; Alghamdi, Abdullah M.; Alqahtani, Yousif A; alqahtani, Abdulaziz Abdulrahman nasser

doi:10.1007/s00044-019-02431-4

Cited by 16 publications

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“…[19] Taha and his group (2019) prepared nineteen bisindolylmethanesulfonamide analogues by a very efficient and practical method. [47,48] The designed products 46 were synthesized by reacting equimolar amounts of 45 with aryl sulphonyl chloride in the presence of pyridine as depicted by scheme 14. Amylase inhibition assay showed comparable inhibitory potential of the synthesized compounds (IC 50 = 1.192 � 0.51-3.057 � 0.18 μM) with respect to acarbose (IC 50 = 0.83 � 0.36 μM).…”

Section: Benzo[b]pyrrole; Fusion Of Benzene Ring To the 23 Positions ...mentioning

confidence: 99%

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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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Section: Benzo[b]pyrrole; Fusion Of Benzene Ring To the 23 Positions ...mentioning

confidence: 99%

“…Taha and his group ( 2019 ) prepared nineteen bisindolylmethanesulfonamide analogues by a very efficient and practical method [47,48] . The designed products 46 were synthesized by reacting equimolar amounts of 45 with aryl sulphonyl chloride in the presence of pyridine as depicted by scheme 14.…”

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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“…Ishnava & Motisariya, indicated that there is a positive correlation between human pancreatic α-amylase activity and the increase in postprandial glucose levels, demonstrating the relevance of suppressing postprandial hyperglycaemia in the T2DM through reduction or inhibition of pancreatic α-amylase activity (10). Taha, et al, considers alpha-amylase inhibitors as the most important tool to control T2DM (14). By inhibiting this enzyme, the rate of absorption of sugars will be slowed down, thereby maintaining homeostatic blood glucose levels due to the inhibited starch digestion [15].…”

Section: Introductionmentioning

confidence: 99%

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2023

IJCRT

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Background: Diabetes mellitus (DM), a group of metabolic disorders characterised by hyperglycaemia, has been attributed to increased activity of α-amylase, one of the key enzymes in carbohydrate metabolism. Alpha amylase inhibition can potentially control postprandial hyperglycaemia, hence significant in the management of diabetes mellitus, especially type 2. Acarbose, the proven α-amylase inhibitor, has been associated with several side effects. Plants used in traditional medicine represent a valuable source in the search for an alternative. The study aimed at determining the combined effect of Piliostigma thonningii and Annona senegalensis leaf extracts on alpha amylase activity.Methodology: Mortar and pestle were used to crush the leaves into powder. The fine powder was dispensed in distilled water. Percolation was used to filter the crude extract, evaporated in a water bath at 65 0C to concentrate the extract then reconstituted. Spectrophotometric assay method was used for alpha amylase activity at 540 nm. Results:The results of the study showed that A. senegalensis inhibited α-amylase by 27%, 32% and 34% at 15, 30 and 45 minutes respectively. P. thonningii exhibited inhibitory effects on α-amylase by 25%, 27% and 37% at 15, 30 and 45 minutes respectively. The combined inhibitory effects of A. senegalensis and P. thonningii on α-amylase were 28%, 37% and 62% at 15, 30 and 45 minutes respectively which are significantly different (p < 0.05) from that of the positive control, acarbose (71% at 45 minutes) Conclusion:This study revealed the increased strength to inhibit alpha amylase enzyme by a combination of A. senegalensis and P. thonningii and a proportional increase in the inhibitory effect with increase in incubation time than their individual potential to inhibit alpha amylase.

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“…Primarily, it is sorted into type-I and type-II DM. Type-I DM is caused due to pancreatic cell injury, and sufficient insulin cannot be produced, while type-II DM is caused through the resistance of insulin or less insulin action in the body [29,30]. The inhibition of α-glucosidase slow the digestion of polysaccharides into core monomers, thereby lowering blood sugar levels [31].…”

Section: Introductionmentioning

confidence: 99%

Bio-Oriented Synthesis of Novel (S)-Flurbiprofen Clubbed Hydrazone Schiff’s Bases for Diabetic Management: In Vitro and In Silico Studies

et al. 2022

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A new series of (S)-flurbiprofen derivatives 4a–4p and 5a–5n were synthesized with different aromatic or aliphatic aldehydes and ketones to produce Schiff’s bases and their structures were confirmed through HR-ESI-MS, 1H, and 13C-NMR spectroscopy. The α-glucosidase inhibitory activities of the newly synthesized compounds were scrutinized, in which six compounds 5k, 4h, 5h, 4d, 4b, and 5i showed potent inhibition in the range of 0.93 to 10.26 µM, respectively, whereas fifteen compounds 4c, 4g, 4i, 4j, 4l, 4m, 4o, 4p, 5c, 5d, 5j, 5l, 5m, 5n and 1 exhibited significant inhibitory activity with IC50 in range of = 11.42 to 48.39 µM. In addition, compounds 5g, 5f, 4k, 4n, and 4f displayed moderate-to-low activities. The modes of binding of all the active compounds were determined through the molecular docking approach, which revealed that two residues, specifically Glu277 and His351 are important in the stabilization of the active compounds in the active site of α-glucosidase. Furthermore, these compounds block the active site with high binding energies (−7.51 to −3.36 kcal/mol) thereby inhibiting the function of the enzyme.

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Synthesis, α-amylase inhibition and molecular docking study of bisindolylmethane sulfonamide derivatives

Cited by 16 publications

References 28 publications

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

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

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Bio-Oriented Synthesis of Novel (S)-Flurbiprofen Clubbed Hydrazone Schiff’s Bases for Diabetic Management: In Vitro and In Silico Studies

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