Synthesis, crystal structure and activity evaluation of novel 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives as protein-tyrosine kinase (PTK) inhibitors
Four new 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives, namely (E)-4-(5-bromo-2-hydroxybenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (7), (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (8), (E)-4-(5-bromo-2-hydroxybenzylidene)-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C18H15BrO5, (9), and (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (10), have been synthesized and characterized by FT-IR, NMR and MS. The structure of (9) was confirmed by single-crystal X-ray diffraction. Crystal structure analysis shows that molecules of (9) are connected into a one-dimensional chain in the [010] direction through classical hydrogen bonds and these chains are further extended into a three-dimensional network via C-H...O interactions. The inhibitory activities of these compounds against protein-tyrosine kinases (PTKs) show that 6-hydroxy-substituted compounds (9) and (10) are more effective for inhibiting ErbB1 and ErbB2 than are 6-methoxy-substituted compounds (7) and (8). This may be because (9) and (10) could effectively bind to the active pockets of the protein through intermolecular interactions.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2017 |
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| Erschienen: |
2017 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:73 |
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| Enthalten in: |
Acta crystallographica. Section C, Structural chemistry - 73(2017), Pt 11 vom: 01. Nov., Seite 1003-1009 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Li, Ning [VerfasserIn] |
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| Links: |
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| Themen: |
3,4-dihydro-1-benzoxepin-5(2H)-ones |
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| Anmerkungen: |
Date Completed 23.03.2018 Date Revised 10.07.2018 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1107/S2053229617015145 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM277786215 |
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| 245 | 1 | 0 | |a Synthesis, crystal structure and activity evaluation of novel 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives as protein-tyrosine kinase (PTK) inhibitors |
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| 500 | |a Date Revised 10.07.2018 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a Four new 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives, namely (E)-4-(5-bromo-2-hydroxybenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (7), (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (8), (E)-4-(5-bromo-2-hydroxybenzylidene)-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C18H15BrO5, (9), and (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (10), have been synthesized and characterized by FT-IR, NMR and MS. The structure of (9) was confirmed by single-crystal X-ray diffraction. Crystal structure analysis shows that molecules of (9) are connected into a one-dimensional chain in the [010] direction through classical hydrogen bonds and these chains are further extended into a three-dimensional network via C-H...O interactions. The inhibitory activities of these compounds against protein-tyrosine kinases (PTKs) show that 6-hydroxy-substituted compounds (9) and (10) are more effective for inhibiting ErbB1 and ErbB2 than are 6-methoxy-substituted compounds (7) and (8). This may be because (9) and (10) could effectively bind to the active pockets of the protein through intermolecular interactions | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a 3,4-dihydro-1-benzoxepin-5(2H)-ones | |
| 650 | 4 | |a PTK inhibitors | |
| 650 | 4 | |a crystal structure | |
| 650 | 4 | |a protein–tyrosine kinase inhibitors | |
| 700 | 1 | |a Yao, Binrong |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Chunhua |e verfasserin |4 aut | |
| 700 | 1 | |a Meng, Qingguo |e verfasserin |4 aut | |
| 700 | 1 | |a Hou, Guige |e verfasserin |4 aut | |
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