Premium
Synthesis and biological evaluation of novel indoleamide derivatives as antioxidative and antitumor agents
Author(s) -
Zhang Zhen,
Gu YingLin,
Wang ZhengYang,
Wang HuanNan,
Zhao Yan,
Chu XueMei,
Zhang ChunYan,
Yan MaoCai
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3853
Subject(s) - chemistry , hela , dpph , amide , cytotoxicity , oxidative stress , carbon 13 nmr , stereochemistry , in vitro , antioxidant , biochemistry
Novel indole amide derivatives C1‐C10 were successfully synthesized and characterized by 1 H NMR, 13 C NMR, IR, MS, and elemental analysis, and their molecular formulas were C 14 H 10 N 6 O, C 13 H 10 N 4 O, C 16 H 13 N 3 O 2 , C 19 H 14 N 2 O 2 , C 16 H 11 N 3 OS, C 15 H 13 N 3 O, C 12 H 9 N 5 O, C 16 H 10 ClN 3 OS, C 15 H 17 N 3 O 2 , and C 13 H 14 N 2 O 3 , respectively. The primary biological activities of these compounds were evaluated in vitro by the DPPH assay, H 2 O 2 ‐induced oxidative stress injury assay, and cytotoxicity assay. The results indicated that compounds C1, C2, C4, C7, and C9 exhibited DPPH·scavenging ability, while C3, C4, C5, and C8 showed potent growth‐inhibitory activities against various human tumor cells, including MDA‐MB‐231, Hela, A549, and HT29. Interestingly, compound C4 showed potent scavenging effects on the DPPH radical and possessed protective effect on H 2 O 2 ‐induced oxidative stress injury in human neuroblastoma SH‐SY5Y cells at low concentrations; however, C4 exhibited significant toxicity against four human tumor cells at a higher concentration in all treatments, and the range of IC 50 value was 7.91 to 13.35 μM.