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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 12, pp 2253–2263 | Cite as

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

  • Samet Poyraz
  • Necmiye Canacankatan
  • Samet Belveren
  • Derya Yetkin
  • Kezban Kibar
  • Mahmut Ülger
  • José M. Sansano
  • Nefise Dilek Özcelik
  • Ş. Necat Yılmaz
  • H. Ali DöndaşEmail author
Original Paper
  • 170 Downloads

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.

Graphical abstract

Keywords

Amino acids Cycloadditions Heterocycles MCF-7 cells Apoptosis Anti(myco)bacterial 

Notes

Acknowledgements

We would like to thank Mersin University, Research Foundation (Project No: BAP 2015-AP2-1342) for financial support.

Supplementary material

706_2018_2286_MOESM1_ESM.pdf (1.4 mb)
Supplementary material 1 (PDF 1452 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Samet Poyraz
    • 1
  • Necmiye Canacankatan
    • 2
  • Samet Belveren
    • 1
  • Derya Yetkin
    • 3
  • Kezban Kibar
    • 3
  • Mahmut Ülger
    • 4
  • José M. Sansano
    • 5
  • Nefise Dilek Özcelik
    • 6
  • Ş. Necat Yılmaz
    • 3
  • H. Ali Döndaş
    • 1
    Email author
  1. 1.Department of Chemistry, Faculty of PharmacyMersin UniversityMersinTurkey
  2. 2.Department of Biochemistry, Faculty of PharmacyMersin UniversityMersinTurkey
  3. 3.Department of Histology and Embryology, Faculty of MedicineMersin UniversityMersinTurkey
  4. 4.Department of Pharmaceutical Microbiology, Faculty of PharmacyMersin UniversityMersinTurkey
  5. 5.Departamento de Química Orgánica, Instituto de Síntesis Orgánica y Centro de Innovación en Química Avanzada (ORFEO-CINQA)Universidad de AlicanteAlicanteSpain
  6. 6.Department of Physics, Faculty of ScienceAksaray UniversityAksarayTurkey

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