Diazaspiro-iminosugars and polyhydroxylated spiro-bislactams: synthesis, glycosidase inhibition and molecular docking studies

Parihar, Vijay Singh; Pawar, Nitin J.; Ghosh, Sougata; Chopade, Balu A.; Kumbhar, Navanath; Dhavale, Dilip D.

doi:10.1039/c5ra09584k

Cited by 16 publications

(7 citation statements)

References 51 publications

(39 reference statements)

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“…Spirocyclic bis‐lactam 235 synthesis was reported by Dhavale and co‐workers [78] . The molecule stands out as a spiro‐iminosugar and was obtained through a two‐step reaction in good overall yield (65%) (Scheme 62).…”

Section: Spiro‐δ‐lactamsmentioning

confidence: 95%

“…Spirocyclic bis-lactam 235 synthesis was reported by Dhavale and co-workers. [78] The molecule stands out as a spiro-iminosugar and was obtained through a twostep reaction in good overall yield (65%) (Scheme 62). The first reaction step comprises an oxidative cleavage of diol 231 followed by NaBH 4 reduction leading to compound 232 which was converted into azide 234 via tosylation of the primary hydroxyl group followed by the reaction with sodium azide.…”

Section: Schmidt-boyer Rearrangementmentioning

confidence: 99%

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Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Alves

Soares

et al. 2021

Adv Synth Catal

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Spirocyclic molecules are widely recognized for their complex three-dimensional features and structural rigidity. Among this class of molecules, the spiro-lactams subclass stands out, being extensively explored due to its bioactivity and utility in a variety of scientific fields such as drug design and organic synthesis. Given the recognition of spirocyclic lactams' broad potential, several efforts have been engaged on the pursuit of new synthetic strategies towards these molecules. The present review gathers advances on the synthesis of both spiroβ-lactams (spiroazetidin-2-ones) and spiro-δ-lactams (spiropiperidon-2-ones) reported since 2015. The work is divided into two distinct parts, each one dedicated to one of these types of spiro-lactam, with the approach used for building the spirocyclic system being extensively discussed, according to the meth-

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Section: Spiro‐δ‐lactamsmentioning

confidence: 95%

Section: Schmidt-boyer Rearrangementmentioning

confidence: 99%

Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Alves

Soares

et al. 2021

Adv Synth Catal

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“…Our group has exploited Corey-link approach with 3-oxo-1,2;5,6-diisopropylidene- d -gluco-furanose to give C 3 -azido-3-formyl-substituted d -gluco-furanose that was elaborated toward the synthesis of spiro-iminosugars VIIIa / VIIIb , which showed a promising α-glucosidase inhibitory activity. 22 In the continuation of our work, we now report the synthesis of tricyclic azepine 1 , piperidine iminosugars 2 , 3a – g , and iminosugars 4a – g spiro-linked with the morpholine-fused 1,2,3-triazol. The conformations 1 C 4 / 4 C 1 were obtained on the basis of the 1 H NMR study and substantiated by density functional theory (DFT) studies.…”

Section: Introductionmentioning

confidence: 93%

Iminosugars Spiro-Linked with Morpholine-Fused 1,2,3-Triazole: Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, Antifungal Assay, and Docking Studies

et al. 2017

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Synthesis of iminosugars 1, 2, 3a, and 4a and N-alkyl (ethyl, butyl, hexyl, octyl, decyl, and dodecyl) derivatives 3b–g and 4b–g spiro-linked with morpholine-fused 1,2,3-triazole is described. Conformation of the piperidine ring in each spiro-iminosugar was evaluated by 1H NMR spectroscopy, and conformational change in N-alkylated compounds 4b–g with respect to parent spiro-iminosugar 4a is supported by density functional theory calculations. Out of 16 new spiro-iminosugars, the spiro-iminosugars 3a (IC50 = 0.075 μM) and 4a (IC50 = 0.036 μM) were found to be more potent inhibitors of α-glucosidase than the marketed drug miglitol (IC50 = 0.100 μM). In addition, 3a (minimum inhibition concentration (MIC) = 0.85 μM) and 4a (MIC = 0.025 μM) showed more potent antifungal activity against Candida albicans than antifungal drug amphotericin b (MIC = 1.25 μM). In few cases, the N-alkyl derivatives showed increase of α-glucosidase inhibition and enhancement of antifungal activity compare to the respective parent iminosugar. The biological activities were further substantiated by molecular docking studies.

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“…However, reports on the metal nanoparticles to show antidiabetic activity are rare and it needs attention. Scavenging of free radicals and inhibition of α-amylase and α-glucosidase, are two important preventive measures of diabetes [15][16][17][18]. Although there are reports on the relationship between metals and enzyme activity, only preliminary studies on relationship between metal nanoparticles and α-glucosidase as well as α-amylase action are reported [19].…”

Section: Introductionmentioning

confidence: 99%

Antidiabetic and Antioxidant Properties of Copper Nanoparticles Synthesized by Medicinal Plant Dioscorea bulbifera

Ghosh¹,

More²,

Nitnavare³

et al. 2015

J Nanomedic Nanotechnol

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Background: Biological route for synthesis of copper nanoparticles (CuNPs) with therapeutic potential is a major challenge. In this study, CuNPs were synthesized by D. bulbifera tuber extract (DBTE) which were further evaluated for antidiabetic and free radical scavenging activity. Methods: CuNPs synthesized by DBTE were characterized by UV-visible spectroscopy, transmission electron microscopy, energy dispersive spectroscopy and dynamic light scattering. CuNPs were checked for α-amylase and α-glucosidase inhibition along with interaction studies employing fluroscence spectroscopy, circular dichroism spectroscopy and computational docking. DPPH, nitric oxide and superoxide radical scavenging activities of CuNPs were also checked. Results: Spherical monodispersed CuNPs were synthesized within 5 h that was indicated by a colour change from pale blue to brown. Majority of the nanoparticles synthesized were found to be between 12 to 16 nm as showed in DLS which grew till a final size of 86 to 126 nm as indicated in TEM. Bioreduced CuNPs showed 38.70 ± 1.45% and 34.72 ± 1.22% inhibition against porcine and murine pancreatic amylase, respectively with an uncompetitive mode that was further confirmed by docking studies. Fluorescence spectroscopy confirmed the interaction of CuNPs to the enzyme via Trp residues while CD spectra indicated the structural and conformational changes on binding of CuNPs to the enzyme. CuNPs exhibited 99.09 ± 0.15% inhibition against α-glucosidase while 90.67 ± 0.33% inhibition against murine intestinal glucosidase, respectively. CuNPs showed 40.81 ± 1.44%, 79.06 ± 1.02% and 48.39 ± 1.46% scavenging activity against DPPH, nitric oxide and superoxide radicals respectively. Conclusion: D.bulbifera tuber extract mediated bioreduction is most rapid route to synthesize novel CuNPs with promising antidiabetic and antioxidant properties. This is the first detailed report which provides intense scientific rationale for the use of CuNPs as nanomedicine for efficient control of T2DM and oxidative stress.

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Diazaspiro-iminosugars and polyhydroxylated spiro-bislactams: synthesis, glycosidase inhibition and molecular docking studies

Cited by 16 publications

References 51 publications

Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Iminosugars Spiro-Linked with Morpholine-Fused 1,2,3-Triazole: Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, Antifungal Assay, and Docking Studies

Antidiabetic and Antioxidant Properties of Copper Nanoparticles Synthesized by Medicinal Plant Dioscorea bulbifera

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