Novel asymmetric 3,5-bis(arylidene)piperidin-4-one derivatives : synthesis, crystal structures and cytotoxicity
3,5-Bis(arylidene)piperidin-4-one derivatives (BAPs) display good antitumour activity because of their double α,β-unsaturated ketone structural characteristics. Reported BAPs have generally been symmetric and asymmetric BAPs have been little documented. Three asymmetric BAPs, namely (5E)-3-(4-tert-butylbenzylidene)-5-(4-fluorobenzylidene)-1-methylpiperidin-4-one, C24H26FNO, (5), (5E)-3-(4-tert-butylbenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one, C26H31NO3, (6), and (5E)-3-{3-[(E)-(2,3-dihydroxybenzylidene)amino]benzylidene}-5-(2-fluorobenzylidene)-1-methylpiperidin-4-one, C27H23FN2O3, (12), were generated by Claisen-Schmidt condensation. They are characterized by NMR and FT-IR spectroscopies, and elemental analysis. Single-crystal structure analysis reveals that the two arylidene rings on both sides of the BAP structures adopt an E stereochemistry of the olefinic double bonds and the compounds are E,E isomers. Molecules of (5) and (12) generate one-dimensional chains through intermolecular hydrogen bonds, while compound (6) generates a two-dimensional network through hydrogen bonds. Preliminary cytotoxicities toward human liver hepatocellular carcinoma cell line (HepG2), human acute mononuclear granulocyte leukaemia (THP-1) and human normal hepatical cell line (LO2) were evaluated.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2018 |
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| Erschienen: |
2018 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:74 |
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| Enthalten in: |
Acta crystallographica. Section C, Structural chemistry - 74(2018), Pt 6 vom: 01. Juni, Seite 659-665 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yao, Binrong [VerfasserIn] |
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| Links: |
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| Themen: |
Antineoplastic Agents |
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| Anmerkungen: |
Date Completed 13.11.2018 Date Revised 13.11.2018 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1107/S2053229618006605 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM285149873 |
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| 245 | 1 | 0 | |a Novel asymmetric 3,5-bis(arylidene)piperidin-4-one derivatives |b synthesis, crystal structures and cytotoxicity |
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| 500 | |a Date Completed 13.11.2018 | ||
| 500 | |a Date Revised 13.11.2018 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a 3,5-Bis(arylidene)piperidin-4-one derivatives (BAPs) display good antitumour activity because of their double α,β-unsaturated ketone structural characteristics. Reported BAPs have generally been symmetric and asymmetric BAPs have been little documented. Three asymmetric BAPs, namely (5E)-3-(4-tert-butylbenzylidene)-5-(4-fluorobenzylidene)-1-methylpiperidin-4-one, C24H26FNO, (5), (5E)-3-(4-tert-butylbenzylidene)-5-(3,5-dimethoxybenzylidene)-1-methylpiperidin-4-one, C26H31NO3, (6), and (5E)-3-{3-[(E)-(2,3-dihydroxybenzylidene)amino]benzylidene}-5-(2-fluorobenzylidene)-1-methylpiperidin-4-one, C27H23FN2O3, (12), were generated by Claisen-Schmidt condensation. They are characterized by NMR and FT-IR spectroscopies, and elemental analysis. Single-crystal structure analysis reveals that the two arylidene rings on both sides of the BAP structures adopt an E stereochemistry of the olefinic double bonds and the compounds are E,E isomers. Molecules of (5) and (12) generate one-dimensional chains through intermolecular hydrogen bonds, while compound (6) generates a two-dimensional network through hydrogen bonds. Preliminary cytotoxicities toward human liver hepatocellular carcinoma cell line (HepG2), human acute mononuclear granulocyte leukaemia (THP-1) and human normal hepatical cell line (LO2) were evaluated | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Claisen-Schmidt condensation | |
| 650 | 4 | |a DAP | |
| 650 | 4 | |a asymmetric | |
| 650 | 4 | |a crystal structure | |
| 650 | 4 | |a cytotoxicity | |
| 650 | 4 | |a piperidin-4-one | |
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| 650 | 7 | |a Piperidines |2 NLM | |
| 700 | 1 | |a Li, Ning |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Chunhua |e verfasserin |4 aut | |
| 700 | 1 | |a Hou, Guige |e verfasserin |4 aut | |
| 700 | 1 | |a Meng, Qingguo |e verfasserin |4 aut | |
| 700 | 1 | |a Yan, Ke |e verfasserin |4 aut | |
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