Catalytic asymmetric synthesis of indole derivatives as novel α-glucosidase inhibitors in vitro

Islam, Mohammad Shahidul; Barakat, Assem; Al‐Majid, Abdullah Mohammed; Ali, Mohammad Ajmal; Yousuf, Sammer; Choudhary, Muhammad Iqbal; Khalil, Ruqaiya; Ul-Haq, Zaheer

doi:10.1016/j.bioorg.2018.05.004

Cited by 49 publications

(16 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, medicinal chemists have designed various active pharmacophores of indole analogs with antidiabetic and antidyslipidemic activities ( Kumari and Singh, 2019 ). For example, a series of enantiomerically pure indole derivatives, 3a-rvia Friedel-Crafts alkylation of indole 1 with enones 2a-r, were designed, some of which were identified as potent inhibitors of α-glucosidase (IC50 = 4.3 ± 0.13–43.9 ± 0.51 μM); the activity is several folds higher than that of acarbose (IC50 = 840 ± 1.73 μM) ( Islam et al, 2018 ). Compound 13 m is a hybrid derivative of indole and triazole, showing effective anti-lipogenesis activity with an IC-50 value of 1.67 μM.…”

Section: Ongoing Research Of Indole and Its Derivatives As An Interventionmentioning

confidence: 99%

New Insights Into Gut-Bacteria-Derived Indole and Its Derivatives in Intestinal and Liver Diseases

Zhang

et al. 2021

Front. Pharmacol.

View full text Add to dashboard Cite

The interaction between host and microorganism widely affects the immune and metabolic status. Indole and its derivatives are metabolites produced by the metabolism of tryptophan catalyzed by intestinal microorganisms. By activating nuclear receptors, regulating intestinal hormones, and affecting the biological effects of bacteria as signaling molecules, indole and its derivatives maintain intestinal homeostasis and impact liver metabolism and the immune response, which shows good therapeutic prospects. We reviewed recent studies on indole and its derivatives, including related metabolism, the influence of diets and intestinal commensal bacteria, and the targets and mechanisms in pathological conditions, especially progress in therapeutic strategies. New research insights into indoles will facilitate a better understanding of their druggability and application in intestinal and liver diseases.

show abstract

Section: Ongoing Research Of Indole and Its Derivatives As An Interventionmentioning

confidence: 99%

New Insights Into Gut-Bacteria-Derived Indole and Its Derivatives in Intestinal and Liver Diseases

Zhang

et al. 2021

Front. Pharmacol.

View full text Add to dashboard Cite

show abstract

“…The treatment of hyperglycaemia is crucial in the management of metabolic syndromes such as type II diabetes [40]. α-Amylase, and α-glucosidase as digestive enzymes play an essential role in the glucose release process, by taking part in the hydrolysis of dietary polysaccharides.…”

Section: Discussionmentioning

confidence: 99%

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase

et al. 2019

Self Cite

View full text Add to dashboard Cite

Inhibition of α-amylase and α-glucosidase by specified synthetic compounds during the digestion of starch helps control post-prandial hyperglycemia and could represent a potential therapy for type II diabetes mellitus. A new series of spiroheterocyclic compounds bearing oxindole/benzofuran/pyrrolidine/thiazolidine motifs were synthesized via a 1,3-dipolar cyclo-addition reaction approach. The specific compounds were obtained by reactions of chalcones having a benzo[b]furan scaffold (compounds 2a–f), with a substituted isatin (compounds 3a–c) and heterocyclic amino acids (compounds 4a,b). The target spiroindolone analogues 5a–r were evaluated for their potential inhibitory activities against the enzymes α-amylase and α-glucosidase. Preliminary results indicated that some of the target compounds exhibit promising α-amylase and α-glucosidase inhibitory activity. Among the tested spiroindolone analogues, the cycloadduct 5r was found to be the most active (IC50 = 22.61 ± 0.54 μM and 14.05 ± 1.03 μM) as α-amylase and α-glucosidase inhibitors, with selectivity indexes of 0.62 and 1.60, respectively. Docking studies were carried out to confirm the binding interaction between the enzyme active site and the spiroindolone analogues.

show abstract

“…The processes were catalyzed by PyBox [43] or iPrBox [44], respectively (Scheme 16). The asymmetric reaction of indoles with α,β-unsaturated carbonyl compounds 45 (enones) was carried out using three similar catalytic systems (Scheme 17) [45][46][47]. In the first contribution, reaction was promoted by imidazoline-oxazoline 46 complex with Cu(OTf) 2 (acetonitrile, room temperature), leading to indole derivatives acting as novel α-glucosidase inhibitors in vitro [45].…”

Section: Asymmetric Friedel-crafts Reactionsmentioning

confidence: 99%

“…The asymmetric reaction of indoles with α,β-unsaturated carbonyl compounds 45 (enones) was carried out using three similar catalytic systems (Scheme 17) [45][46][47]. In the first contribution, reaction was promoted by imidazoline-oxazoline 46 complex with Cu(OTf) 2 (acetonitrile, room temperature), leading to indole derivatives acting as novel α-glucosidase inhibitors in vitro [45]. The second approach comprises a utilization of chiral N,N-dioxide 47-scandium(III) complexes in dichloromethane at 35 • C [46], and finally, the third work relies on the application of cationic aqua complex of 2,2 -bypiridine 48 with palladium(II) in water at room temperature [47].…”

Section: Asymmetric Friedel-crafts Reactionsmentioning

confidence: 99%

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

2021

View full text Add to dashboard Cite

The main purpose of this review article is to present selected asymmetric synthesis reactions in which chemical and stereochemical outcomes are dependent on the use of an appropriate chiral catalyst. Optically pure or enantiomerically enriched products of such transformations may find further applications in various fields. Among an extremely wide variety of asymmetric reactions catalyzed by chiral systems, we are interested in: asymmetric cyclopropanation, Friedel–Crafts reaction, Mannich and Michael reaction, and other stereoselective processes conducted in the presence of zinc ions. This paper describes the achievements of the above-mentioned asymmetric transformations in the last three years. The choice of reactions is related to the research that has been carried out in our laboratory for many years.

show abstract

Catalytic asymmetric synthesis of indole derivatives as novel α-glucosidase inhibitors in vitro

Cited by 49 publications

References 30 publications

New Insights Into Gut-Bacteria-Derived Indole and Its Derivatives in Intestinal and Liver Diseases

New Insights Into Gut-Bacteria-Derived Indole and Its Derivatives in Intestinal and Liver Diseases

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase

Recent Advances in Selected Asymmetric Reactions Promoted by Chiral Catalysts: Cyclopropanations, Friedel–Crafts, Mannich, Michael and Other Zinc-Mediated Processes—An Update

Contact Info

Product

Resources

About