Synthesis of Tumor Selective Indole and 8-Hydroxyquinoline Skeleton Containing Di-, or Triarylmethanes with Improved Cytotoxic Activity
The reaction between glycine-type aminonaphthol derivatives substituted with 2- or 1-naphthol and indole or 7-azaindole has been tested. Starting from 2-naphthol as a precursor, the reaction led to the formation of ring-closed products, while in the case of a 1-naphthol-type precursor, the desired b...
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| Main Authors: | |
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| Format: | Article |
| Published: |
2024
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| Series: | MOLECULES
29 No. 17 |
| Subjects: | |
| doi: | 10.3390/molecules29174176 |
| mtmt: | 35201147 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/34523 |
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| 024 | 7 | |a 10.3390/molecules29174176 |2 doi | |
| 024 | 7 | |a 35201147 |2 mtmt | |
| 040 | |a SZTE Publicatio Repozitórium |b hun | ||
| 041 | |a eng | ||
| 100 | 1 | |a Hegedűs Dóra | |
| 245 | 1 | 0 | |a Synthesis of Tumor Selective Indole and 8-Hydroxyquinoline Skeleton Containing Di-, or Triarylmethanes with Improved Cytotoxic Activity |h [elektronikus dokumentum] / |c Hegedűs Dóra |
| 260 | |c 2024 | ||
| 300 | |a 14 | ||
| 490 | 0 | |a MOLECULES |v 29 No. 17 | |
| 520 | 3 | |a The reaction between glycine-type aminonaphthol derivatives substituted with 2- or 1-naphthol and indole or 7-azaindole has been tested. Starting from 2-naphthol as a precursor, the reaction led to the formation of ring-closed products, while in the case of a 1-naphthol-type precursor, the desired biaryl ester was isolated. The synthesis of a bifunctional precursor starting from 5-chloro-8-hydroxyquinoline, morpholine, and ethyl glyoxylate via modified Mannich reaction is reported. The formed Mannich base 10 was subjected to give bioconjugates with indole and 7-azaindole. The effect of the aldehyde component and the amine part of the Mannich base on the synthetic pathway was also investigated. In favor of having a preliminary overview of the structure-activity relationships, the derivatives have been tested on cancer and normal cell lines. In the case of bioconjugate 16, as the most powerful scaffold in the series bearing indole and a 5-chloro-8-hydroxyquinoline skeleton, a potent toxic activity against the resistant Colo320 colon adenocarcinoma cell line was observed. Furthermore, this derivative was selective towards cancer cell lines showing no toxicity on non-tumor fibroblast cells. | |
| 650 | 4 | |a Általános orvostudomány | |
| 700 | 0 | 1 | |a Szemerédi Nikoletta |e aut |
| 700 | 0 | 1 | |a Petrinca Krisztina |e aut |
| 700 | 0 | 1 | |a Berkecz Róbert |e aut |
| 700 | 0 | 1 | |a Spengler Gabriella |e aut |
| 700 | 0 | 1 | |a Szatmári István |e aut |
| 856 | 4 | 0 | |u http://publicatio.bibl.u-szeged.hu/34523/1/Molecules_4176_Hegedus_2024.pdf |z Dokumentum-elérés |