Methoxy-activated indole-7-carbohydrazides; synthesis, antioxidant, and anticancer properties

Kandemir H., İzgi S., Cınar I., Cebeci F., DİRİCAN E., Saglam M. F., ...More

Journal of Heterocyclic Chemistry, vol.60, no.1, pp.74-85, 2023 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 60 Issue: 1
  • Publication Date: 2023
  • Doi Number: 10.1002/jhet.4562
  • Journal Name: Journal of Heterocyclic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), Chemical Abstracts Core, Chimica
  • Page Numbers: pp.74-85
  • Bilecik Şeyh Edebali University Affiliated: No

Abstract

Indole has been known as a key heterocyclic motif in the development of new structures for both chemical and biological properties. In this current study, a new range of indole-7-carbohydrazides has been successfully synthesized starting from the readily available 3-phenyl and 2,3-diphenyl 4,6-dimethoxyindoles. The structures of the novel compounds were confirmed by utilizing 1H NMR, 13C NMR, FT-IR, high-resolution mass spectrometry, and single crystal X- ray diffraction techniques. In addition, the indole-7-carbohydrazides showed promising antioxidant results in preliminary screens. Some of the new compounds generated from dimethoxy indoles were also screened for their anticancer activity against SH-SHY5Y (human neuroblastoma), AGS (human gastric adenocarcinoma), and MDA-MB-231 (human breast adenocarcinoma) cell lines. The results revealed that the compound 12 was the promising candidate, showing cytotoxic effects on both neuroblastoma, stomach, and breast cancer cells.