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Natthiya Saehlim. Synthesis of acetylene glycoside analogues and evaluation of their tyrosinase inhibitory activity and synthesis of 3,3-' (Phenylmethylene) BIS [1-(1,2,3-Triazolylmenthyl)] indole derivatives VIA one-pot reaction. Doctoral Degree(Chemistry). Burapha University. Library. : Burapha University, 2021.
Synthesis of acetylene glycoside analogues and evaluation of their tyrosinase inhibitory activity and synthesis of 3,3-' (Phenylmethylene) BIS [1-(1,2,3-Triazolylmenthyl)] indole derivatives VIA one-pot reaction
Name: Natthiya Saehlim
Classification :.DDC: 665.85
LCSH:
Acetylene
Abstract:
In this thesis, we designed, synthesized and evaluated tyrosinase inhibitory activity of acetylene glycosides analogues, as well as developing a new strategy for the synthesis of bis-indole triazole derivatives through one-pot multi-step reaction. In the first part, acetylene glycoside analogues were synthesized by modifing at C-1 and C-6 positions of sugar with various of alkyne through glycosylation and alkylation. All the products were obtained in good yields and evaluated for their tyrosinase inhibitory activity. 2,3,4,6-Tetra-O-benzyl-1-O-(2-butynyl)-D-glucopyranoside (2d) showed excellent tyrosinase inhibitory activity (IC50 = 54.0 µM) against L-tyrosine, while 2,3,4,6-tetra-O-benzyl-1-O-butynyl-D-glucopyranoside (2b) exhibited potent activities (IC50 = 34.3 µM) against L- DOPA, which was higher than arbutin. Kinetic study revealed that compound 2b was a non-competitive inhibitor with the best Ki value of 21 µM and formed an irreversible complex with mushroom tyrosinase. The SARs results showed that the type of alkyne and alkyl groups at C-6 position on sugar and anomer of products played an important role in their inhibitory activities. In the second part, a new strategy for the synthesis of bis-indole triazoles was developed using onepot four-step procedure. The reaction was carried out using I2 combined with H2SO4- silica catalyzed in Friedel-Crafts reaction of indole with aldehyde followed by Npropargylation, azidation and copper(I)-catalyzed azide alkyne cycloaddition (CuAAC). The reaction proceeded smoothly at room temperature in short time and a series of bis-indole triazoles were obtained in good to excellent yields proving the generality of this one pot methodology
Burapha University. Library
Address:
CHONBURI
Email:
buulibrary@buu.ac.th
Name: Rungnapha Saeeng
Role:
Principal advisor
Created:
2021
Modified:
2022-05-12
Issued:
2022-05-12
วิทยานิพนธ์/Thesis
application/pdf
CallNumber:
Th 665.85 Na282S
eng
DegreeName: Doctor of Philosophy
Level: Doctoral Degree
Descipline: Chemistry
Grantor: Burapha University
©copyrights Burapha University
RightsAccess:
ใช้เวลา
0.028367 วินาที
Natthiya Saehlim
| Title | Contributor | Type |
|---|---|---|
| Synthesis of acetylene glycoside analogues and evaluation of their tyrosinase inhibitory activity and synthesis of 3,3-' (Phenylmethylene) BIS [1-(1,2,3-Triazolylmenthyl)] indole derivatives VIA one-pot reaction
มหาวิทยาลัยบูรพา Natthiya Saehlim | Rungnapha Saeeng | วิทยานิพนธ์/Thesis |
Rungnapha Saeeng