Study of the anti(myco)bacterial and antitumor activities of prolinate and N-amidocarbothiolprolinate derivatives based on fused tetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione, bearing an indole ring

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Poyraz S., Canacankatan N., Belveren S., Yetkin D., Kibar K., Ulger M., ...More

MONATSHEFTE FUR CHEMIE, vol.149, no.12, pp.2253-2263, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 149 Issue: 12
  • Publication Date: 2018
  • Doi Number: 10.1007/s00706-018-2286-8
  • Journal Name: MONATSHEFTE FUR CHEMIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2253-2263
  • Çukurova University Affiliated: No

Abstract

A series of prolinate and N-amidocarbothiolprolinate derivatives based on a fused pyrrole-3,4-dione core, bearing indole ring systems, are prepared from the corresponding amino acid and an aldehyde via thermal 1,3-dipolar cycloaddition of azomethine ylides and condensation with benzoylisothiocyanate. Products are fully characterized by NMR, FT-IR, MS, and an X-ray crystal structure. The prepared compounds are screened for their antibacterial activity against a range of Gram-positive and Gram-negative bacteria and their antimycobacterial activity against M. tuberculosis H37Rv strain. In addition, two selected target compounds are evaluated for cytotoxicity, apoptosis, and anti-inflammatory effects on MCF-7 (breast carcinoma) cell lines. The incorporation of indole ring and -C(O)NHC(S)- moiety resulted to be beneficial since the biological point of view.