Design, synthesis, and anticancer evaluation of 1-benzo[1,3]dioxol-5-yl-3-N-fused heteroaryl indoles
© 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG..
A series of 1-benzo[1,3]dioxol-5-yl-indoles bearing 3-N-fused heteroaryl moieties have been designed based on literature reports of the activity of indoles against various cancer cell lines, synthesized via a Pd-catalyzed C-N cross-coupling, and evaluated for their anticancer activity against prostate (LNCaP), pancreatic (MIA PaCa-2), and acute lymphoblastic leukemia (CCRF-CEM) cancer cell lines. A detailed structure-activity relationship study culminated in the identification of 3-N-benzo[1,2,5]oxadiazole 17 and 3-N-2-methylquinoline 20, whose IC50 values ranged from 328 to 644 nM against CCRF-CEM and MIA PaCa-2. Further mechanistic studies revealed that 20 caused cell cycle arrest at the S phase and induced apoptosis in CCRF-CEM cancer cells. These 1-benzo[1,3]dioxol-5-yl-3-N-fused heteroaryl indoles may serve as a template for further optimization to afford more active analogs and develop a comprehensive understanding of the structure-activity relationships of indole anticancer molecules.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - year:2023 |
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| Enthalten in: |
Molecular diversity - (2023) vom: 03. Feb. |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yao, Chun-Hsu [VerfasserIn] |
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| Links: |
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| Themen: |
3-N-Fused heteroaryl indoles |
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| Anmerkungen: |
Date Revised 16.02.2024 published: Print-Electronic Citation Status Publisher |
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| doi: |
10.1007/s11030-023-10605-x |
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| Förderinstitution / Projekttitel: |
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NLM35245220X |
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| 520 | |a © 2023. The Author(s), under exclusive licence to Springer Nature Switzerland AG. | ||
| 520 | |a A series of 1-benzo[1,3]dioxol-5-yl-indoles bearing 3-N-fused heteroaryl moieties have been designed based on literature reports of the activity of indoles against various cancer cell lines, synthesized via a Pd-catalyzed C-N cross-coupling, and evaluated for their anticancer activity against prostate (LNCaP), pancreatic (MIA PaCa-2), and acute lymphoblastic leukemia (CCRF-CEM) cancer cell lines. A detailed structure-activity relationship study culminated in the identification of 3-N-benzo[1,2,5]oxadiazole 17 and 3-N-2-methylquinoline 20, whose IC50 values ranged from 328 to 644 nM against CCRF-CEM and MIA PaCa-2. Further mechanistic studies revealed that 20 caused cell cycle arrest at the S phase and induced apoptosis in CCRF-CEM cancer cells. These 1-benzo[1,3]dioxol-5-yl-3-N-fused heteroaryl indoles may serve as a template for further optimization to afford more active analogs and develop a comprehensive understanding of the structure-activity relationships of indole anticancer molecules | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a 3-N-Fused heteroaryl indoles | |
| 650 | 4 | |a Antiproliferative activity | |
| 650 | 4 | |a Apoptosis | |
| 650 | 4 | |a Cell cycle analysis | |
| 650 | 4 | |a Pd-catalyzed C-N cross-coupling | |
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| 700 | 1 | |a Song, Jen-Shin |e verfasserin |4 aut | |
| 700 | 1 | |a Huang, Hsing-Hao |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Yu-Chun |e verfasserin |4 aut | |
| 700 | 1 | |a Lee, Jinq-Chyi |e verfasserin |4 aut | |
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