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

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 benzoylisothiocyanat...

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Bibliographic Details
Published in:Monatshefte für Chemie 2018-12, Vol.149 (12), p.2253-2263
Main Authors: Poyraz, Samet, Canacankatan, Necmiye, Belveren, Samet, Yetkin, Derya, Kibar, Kezban, Ülger, Mahmut, Sansano, José M., Özcelik, Nefise Dilek, Necat Yılmaz, Ş., Döndaş, H. Ali
Format: Article
Language:English
Subjects:
Analytical Chemistry
Anticancer properties
Apoptosis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Condensates
Crystal structure
Cycloaddition
Derivatives
Inorganic Chemistry
Iridium
NMR
Nuclear magnetic resonance
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
Toxicity
Tuberculosis
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Summary: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
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-018-2286-8