Details

Autor(en) / Beteiligte

• Giang, Nguyen Thi Kim
• Thanh, Nguyen Dinh
• Quyen, Tran Ha
• Huong, Doan Thi
• Toan, Vu Ngoc
• Van, Hoang Thi Kim

Titel

Synthesis, bacterial and fungal inhibition assay, molecular docking study of substituted isatin (N-substituted 1,2,3,4-tetra-O-acetyl-β-glucopyranosyl)thiosemicarbazones

Ist Teil von

• Medicinal chemistry research, 2022-09, Vol.31 (9), p.1461-1475

Ort / Verlag

New York: Springer US

Erscheinungsjahr

2022

Quelle

SpringerLink

Beschreibungen/Notizen

• Some substituted isatins 3a–3c were prepared by Sandmeyer’s synthesis from different substituted anilines 1a–1c and transformed into corresponding N -alkyl isatins 4a–4j . These substituted N -alkyl isatins were condensed with N -(2,3,4,6-tetra- O -acetyl-β -d- glucopyranosyl)thiosemicarbazide to give new substituted isatin N -(2,3,4,6-tetra- O -acetyl-β -d- glucopyranosyl)thiosemicarbazones 6a–6j with different substituents at 1-, 5- and 7- as well as 5,7-positions of isatin ring. The antibacterial as well as antifungal activity of these thiosemicarbazones was estimated using minimum inhibitory concentration protocol. Amongst these compounds, 6h , 6c , and 6h had excellent inhibitory activity against Staphylococcus aureus , and 6h was the best active one. Induced fit docking and MM-GBSA study was showed that compound 6h had binding efficiency and steric interactions in the active site of S. aureus DNA Gyrase (2XCS) with three hydrogen-bonding interactions to residues Arg1122 on chain B, Asp1083 and Arg1122 on chain D, which suggested that the tested compound inhibited this enzyme in S. aureus . Graphical abstract