TY - GEN
T1 - Synthesis of 5′-bromo-1,1″-bis(2-chlorobenzyl)-[3,3′:3′,3″-terindolin]-2′-one
AU - Adawiyah, Robi'atul
AU - Fadlan, Arif
AU - Santoso, Mardi
N1 - Publisher Copyright:
© 2023 American Institute of Physics Inc.. All rights reserved.
PY - 2023/1/27
Y1 - 2023/1/27
N2 - Isatin is a privileged framework in the drug development and drug design area. Trisindoline, an isatin derivative, acts as a lead compound for the development of α-glucosidase inhibitors. The presence of the bromo group at C5 position of isatin and halogens at the ortho- position of N-benzyl of indole have been reported to be pivotal for the inhibitory activity of α-glucosidase. This paper reports the synthesis of 5′-bromo-1,1″-bis(2-chlorobenzyl)-[3,3′:3′,3″-terindolin]-2′-one (1) by indole N-benzylation and electrophilic addition. Reaction of indole and 2-chlorobenzyl bromide in DMF afforded 2-chlorobenzyl indole. The subsequent reaction of this product with 5-bromoisatin in THF in presence of sulfuric acid yielded the title compound 1. The spectroscopic methods (FTIR, HRMS-ESI, 1H and 13C NMR) were utilized for structure identification of all compounds. The synthesis of compound 1 was successful and it was obtained in 75% yield.
AB - Isatin is a privileged framework in the drug development and drug design area. Trisindoline, an isatin derivative, acts as a lead compound for the development of α-glucosidase inhibitors. The presence of the bromo group at C5 position of isatin and halogens at the ortho- position of N-benzyl of indole have been reported to be pivotal for the inhibitory activity of α-glucosidase. This paper reports the synthesis of 5′-bromo-1,1″-bis(2-chlorobenzyl)-[3,3′:3′,3″-terindolin]-2′-one (1) by indole N-benzylation and electrophilic addition. Reaction of indole and 2-chlorobenzyl bromide in DMF afforded 2-chlorobenzyl indole. The subsequent reaction of this product with 5-bromoisatin in THF in presence of sulfuric acid yielded the title compound 1. The spectroscopic methods (FTIR, HRMS-ESI, 1H and 13C NMR) were utilized for structure identification of all compounds. The synthesis of compound 1 was successful and it was obtained in 75% yield.
UR - http://www.scopus.com/inward/record.url?scp=85147315017&partnerID=8YFLogxK
U2 - 10.1063/5.0106754
DO - 10.1063/5.0106754
M3 - Conference contribution
AN - SCOPUS:85147315017
T3 - AIP Conference Proceedings
BT - 3rd International Conference on Science, Mathematics, Environment, and Education
A2 - Indriyanti, Nurma Yunita
A2 - Sari, Meida Wulan
PB - American Institute of Physics Inc.
T2 - 3rd International Conference on Science, Mathematics, Environment, and Education: Flexibility in Research and Innovation on Science, Mathematics, Environment, and Education for Sustainable Development, ICoSMEE 2021
Y2 - 27 July 2021 through 28 July 2021
ER -