New triazinoindole bearing thiazole/oxazole analogues: Synthesis, α-amylase inhibitory potential and molecular docking study

[Display omitted] •Synthesis of triazinoindole bearing thiazole/oxazole analogues.•In vitro α-amylase activity.•Identification of a new class of α-amylase activity.•Structure Activity Relationship established.•Molecular docking. New triazinoindole bearing thiazole/oxazole analogues (1–21) were synth...

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Veröffentlicht in:Bioorganic chemistry 2019-11, Vol.92, p.103284-103284, Article 103284
Hauptverfasser: Rahim, Fazal, Tariq, Sundas, Taha, Muhammad, Ullah, Hayat, Zaman, Khalid, Uddin, Imad, Wadood, Abdul, Khan, Aftab Ahmad, Rehman, Ashfaq Ur, Uddin, Nizam, Zafar, Salman, Shah, Syed Adnan Ali
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Sprache:eng
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Zusammenfassung:[Display omitted] •Synthesis of triazinoindole bearing thiazole/oxazole analogues.•In vitro α-amylase activity.•Identification of a new class of α-amylase activity.•Structure Activity Relationship established.•Molecular docking. New triazinoindole bearing thiazole/oxazole analogues (1–21) were synthesized and characterized through spectroscopic techniques such as HREI-MS, 1H and 13C NMR. The configuration of compound 2i and 2k was confirmed through NOESY. All analogues were evaluated against α-amylase inhibitory potential. Among the synthesized analogues, compound 1h, 1i, 1j, 2a and 2f having IC50 values 1.80 ± 0.20, 1.90 ± 0.30, 1.2 ± 0.30, 1.2 ± 0.01 and 1.30 ± 0.20 μM respectively, showed excellent α-amylase inhibitory potential when compared with acarbose as standard (IC50 = 0.91 ± 0.20 µM). All other analogues showed good to moderate inhibitory potential. Structural activity relationship (SAR) has been established and binding interactions were confirmed through docking studies.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2019.103284