Prototropic equilibrium in 1(11)H-2, 3, 4, 5-tetrahydro[1, 3]diazepino[1, 2-a]benzimidazole, synthesis and pharmacological properties of its N-substituted derivatives

Морковник, А. С.; Spasov, A. A.; Кузьменко, Т. А.; Kucheryavenko, A. F.; Диваева, Л. Н.; Koshchienko, Yu. V.; Anisimova, V. A.; Kuzmina, L. G.; Рогова, Н В; Кузнецова, В. А.; Chepljaeva, N. I.; Solovyova, O. A.; Таран, А. С.; Vorobiev, E. S.; Aleshin, D. A.; Сиротенко, В. С.; Gajdukova, K. A.; Bogoslavtseva, M. V.

doi:10.1007/s11172-015-1200-3

Cited by 10 publications

(6 citation statements)

References 11 publications

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“…Reaction mixture contained 500 mM glucose, 1 mg/mL bovine serum albumin (BSA) and 0.02% sodium azide in phosphate buffer (pH 7.4) . Tested substances were dissolved in DMSO and added to the final concentrations of 1 · 10 −3 M and 1 · 10 −4 M. Equal volume of solvent was added to the control samples.…”

Section: Methodsmentioning

confidence: 99%

“…To measure the DPP4 activity by using the colorimetrical analysis, glycyl‐prolyl‐ p ‐nitroanilide (Gly‐Pro‐pNA) was used as chromogenic substrate, as described earlier . In a 96‐well plate 40 mL human plasma samples were incubated with test compounds and 0.1 M Tris buffer (pH 8.0) for 5 min.…”

Section: Methodsmentioning

confidence: 99%

“…In a 96‐well plate rabbit muscle glycogen phosphorylase (Sigma, USA) was incubated with test compounds and reaction mixture for 30 min. Phosphate was measured at 620 nm using Infinite M200 PRO microplate reader (Tecan, Austria), 20 min after the termination of the reaction with 150 mL of 1 M HCl containing 1.05% ammonium molybdate and 0.034% malachite green . Test compound was replaced with 50 mM HEPES buffer (pH 8.0) in negative control experiments.…”

Section: Methodsmentioning

confidence: 99%

“…In a 96‐well plate the 0.01 mg/mL enzyme solution (expressed in Saccharomyces cerevisiae ) was incubated with test compounds and phosphate buffer at 37°C for 5 min. Then, 25 mL of 5 mM p ‐nitrophenyl‐α‐ d ‐glucopyranoside was added and the change in absorbance was recorded at 400 nm for 15 min with Infinite M200 PRO microplate reader (Tecan, Austria) . Test compound was replaced with 0.1 M phosphate buffer (pH 6.8) in negative control experiments.…”

Section: Methodsmentioning

confidence: 99%

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6‐Nitroazolo[1,5‐a]pyrimidin‐7(4H)‐ones as Antidiabetic Agents

Spasov

Babkov

Sysoeva

et al. 2017

Archiv der Pharmazie

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Prevention of the formation of advanced glycation end-products (AGEs) is a reliable approach to achieve control over hyperglycemia and the associated pathogenesis of diabetic vascular complications. In these terms, new synthetic approaches to 6-nitroazolo[1,5-a]pyrimidines have been developed on the basis of the promising antiglycation activity of their structural analogues, such as azolo[5,1-c][1,2,4]triazine-4(1H)-ones. A number of nitroazolopyrimidines were obtained by using nitration, chlorodeoxygenation, and amination reactions, and their antidiabetic properties were elucidated in vitro. It was shown that triazolo[1,5-a]pyrimidine-7(4H)-ones exhibit a higher antiglycation activity than the corresponding 7-alkylamino analogs and aminoguanidine, as the reference compound. It is suggested that this kind of activity can be associated with the chelating properties possessed by the synthesized 6-nitro-7-oxoderivatives. Furthermore, the compounds obtained were tested for their inhibitory activity against dipeptidyl peptidase 4 (DPP4), glycogen phosphorylase, and α-glucosidase in vitro, but their activities proved to be significantly inferior to those of the reference compounds.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

6‐Nitroazolo[1,5‐a]pyrimidin‐7(4H)‐ones as Antidiabetic Agents

Spasov

Babkov

Sysoeva

et al. 2017

Archiv der Pharmazie

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“…In 2015, a Russian group showed that shifting the benzene ring from the diazepine to the imidazole also led to compounds with antiaggregating activity 279 . About 10 compounds were synthesized in this series and tested in vitro.…”

Section: Activity On Unknown Targetsmentioning

confidence: 99%

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

Malki

Martinez

Masurier

2021

Medicinal Research Reviews

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Privileged structures have been widely used as effective templates for drug discovery. While benzo‐1,4‐diazepine constitutes the first historical example of such a structure, the 1,3 analogue is just as rich in terms of applications in medicinal chemistry. The 1,3‐diazepine moiety is present in numerous biological active compounds including natural products, and is used to design compounds displaying a large range of biological activities. It is present in the clinically used anticancer compound pentostatin, in several recent FDA approved β‐lactamase inhibitors (e.g., avibactam) and also in coformycin, a natural product known as a ring‐expanded purine analogue displaying antiviral and anticancer activities. Several other 1,3‐diazepine containing compounds have entered into clinical trials. This heterocyclic structure has been and is still widely used in medicinal chemistry to design enzyme inhibitors, GPCR ligands, and so forth. This review endeavours to highlight the main use of the 1,3‐diazepine scaffold and its derivatives, and their applications in medicinal chemistry, drug design, and therapy. We will focus more particularly on the development of enzyme inhibitors incorporating this scaffold, with a strong emphasis on the molecular interactions involved in the inhibition mechanism.

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1,3-Diazepines

Gilles

Borggraeve

2022

Comprehensive Heterocyclic Chemistry IV

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Prototropic equilibrium in 1(11)H-2, 3, 4, 5-tetrahydro[1, 3]diazepino[1, 2-a]benzimidazole, synthesis and pharmacological properties of its N-substituted derivatives

Cited by 10 publications

References 11 publications

6‐Nitroazolo[1,5‐a]pyrimidin‐7(4H)‐ones as Antidiabetic Agents

6‐Nitroazolo[1,5‐a]pyrimidin‐7(4H)‐ones as Antidiabetic Agents

1,3‐Diazepine: A privileged scaffold in medicinal chemistry

1,3-Diazepines

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