The synthesis of new oxindoles as analogs of natural product 3,3$^\prime $-bis(indolyl)oxindole and in vitro evaluation of the enzyme activity of G6PD and 6PGD

Authors

SİNAN BAYINDIR
ADNAN AYNA
YUSUF TEMEL
MEHMET ÇİFTCİ

DOI

10.3906/kim-1706-51

Abstract

Natural and synthetic derivatives that contain an indole core are being used in medical treatments and technological processes. Therefore, the development of new synthetic methods for the synthesis of indole derivatives is very popular. In this study, new oxindoles with reaction of 4,7-dihydro-1$H$-indole (2) and isatin (4) were synthesized as analogs of natural product 3,3$^\prime $-bis(indolyl)oxindole. The biological properties of the compounds obtained during this study were also studied, showing that compounds 5, 7, and 12 inhibited the activity of G6PD with an IC$_{50}$ of 99 $\mu $M, 231 $\mu $M, and 304 $\mu $M respectively. The activity of rat erythrocyte 6PGD was increased in the presence of 5 and 7 and was inhibited in the presence of 12. As indole derivative 5 was an activator of 6PGD and inhibitor of G6PD, it was selected for docking studies to understand the mechanism of activation and inhibition.

Keywords

Oxindoles, natural product, 3, 3$^\prime $-bis(indolyl)oxindole, enzyme, 6PGD, G6P

First Page

332

Last Page

345

Recommended Citation

BAYINDIR, SİNAN; AYNA, ADNAN; TEMEL, YUSUF; and ÇİFTCİ, MEHMET (2018) "The synthesis of new oxindoles as analogs of natural product 3,3$^\prime $-bis(indolyl)oxindole and in vitro evaluation of the enzyme activity of G6PD and 6PGD," Turkish Journal of Chemistry: Vol. 42: No. 2, Article 11. https://doi.org/10.3906/kim-1706-51
Available at: https://journals.tubitak.gov.tr/chem/vol42/iss2/11