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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Title: 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
Authors: Poyraz, Samet | Canacankatan, Necmiye | Belveren, Samet | Yetkin, Derya | Kibar, Kezban | Ülger, Mahmut | Sansano, Jose M. | Özcelik, Nefise Dilek | Yılmaz, Ş. Necat | Döndaş, H. Ali
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Amino acids | Cycloadditions | Heterocycles | MCF-7 cells | Apoptosis | Anti(myco)bacterial
Knowledge Area: Química Orgánica
Issue Date: Dec-2018
Publisher: Springer Vienna
Citation: Monatshefte für Chemie - Chemical Monthly. 2018, 149(12): 2253-2263. doi:10.1007/s00706-018-2286-8
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.
Sponsor: We would like to thank Mersin University, Research Foundation (Project No: BAP 2015-AP2-1342) for financial support.
URI: http://hdl.handle.net/10045/83350
ISSN: 0026-9247 (Print) | 1434-4475 (Online)
DOI: 10.1007/s00706-018-2286-8
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Springer-Verlag GmbH Austria, part of Springer Nature 2018
Peer Review: si
Publisher version: https://doi.org/10.1007/s00706-018-2286-8
Appears in Collections:INV - SINTAS - Artículos de Revistas

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