Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents
Natural products and their analogs have been explored to stop the progression of cancer cells without unwanted side effects. Chalcones, compounds synthesized naturally in plants, have demonstrated potential as anti-cancer treatments. A library of bis-chalcones that are similar in structure to EF-24,...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
De Gruyter
2023-04-01
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| Series: | Heterocyclic Communications |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/hc-2022-0162 |
| _version_ | 1797832450244608000 |
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| author | Smith Robert B. Roberts William Upenieks Mary Gibson Maya Z. Wentzel Michael T. Grice Kyle A. Zingales Sarah K. |
| author_facet | Smith Robert B. Roberts William Upenieks Mary Gibson Maya Z. Wentzel Michael T. Grice Kyle A. Zingales Sarah K. |
| author_sort | Smith Robert B. |
| collection | DOAJ |
| description | Natural products and their analogs have been explored to stop the progression of cancer cells without unwanted side effects. Chalcones, compounds synthesized naturally in plants, have demonstrated potential as anti-cancer treatments. A library of bis-chalcones that are similar in structure to EF-24, a bis-chalcone molecule known to have anti-cancer properties, has been synthesized in order to examine their medicinal properties. This report highlights the synthesis of ten novel analogs, their anti-cancer activities, and conformational analysis via cryo-NMR and corroboration by density functional theory calculations of the lead compound 1b, tert-butyl 3,5-bis((E)-4-methylbenzylidene)-4-oxopiperidine-1-carboxylate. |
| first_indexed | 2024-04-09T14:08:01Z |
| format | Article |
| id | doaj.art-c8f38322fa564bcd8995ac772be7d7b6 |
| institution | Directory Open Access Journal |
| issn | 2191-0197 |
| language | English |
| last_indexed | 2024-04-09T14:08:01Z |
| publishDate | 2023-04-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Heterocyclic Communications |
| spelling | doaj.art-c8f38322fa564bcd8995ac772be7d7b62023-05-06T15:58:55ZengDe GruyterHeterocyclic Communications2191-01972023-04-01291337680310.1515/hc-2022-0162Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agentsSmith Robert B.0Roberts William1Upenieks Mary2Gibson Maya Z.3Wentzel Michael T.4Grice Kyle A.5Zingales Sarah K.6Department of Chemistry, Georgia Southern University, Savannah, GA, 31419, USADepartment of Chemistry, University of Saint Joseph, West Hartford, CT, 06117, USADepartment of Chemistry, University of Saint Joseph, West Hartford, CT, 06117, USADepartment of Chemistry, Georgia Southern University, Savannah, GA, 31419, USADepartment of Chemistry, Augsburg University, Minneapolis, MN, 55454, USADepartment of Chemistry and Biochemistry, Depaul University, Chicago, IL, 60614, USADepartment of Chemistry, Georgia Southern University, Savannah, GA, 31419, USANatural products and their analogs have been explored to stop the progression of cancer cells without unwanted side effects. Chalcones, compounds synthesized naturally in plants, have demonstrated potential as anti-cancer treatments. A library of bis-chalcones that are similar in structure to EF-24, a bis-chalcone molecule known to have anti-cancer properties, has been synthesized in order to examine their medicinal properties. This report highlights the synthesis of ten novel analogs, their anti-cancer activities, and conformational analysis via cryo-NMR and corroboration by density functional theory calculations of the lead compound 1b, tert-butyl 3,5-bis((E)-4-methylbenzylidene)-4-oxopiperidine-1-carboxylate.https://doi.org/10.1515/hc-2022-0162bis-chalconecurcuminanti-cancerdynamic nmrdft |
| spellingShingle | Smith Robert B. Roberts William Upenieks Mary Gibson Maya Z. Wentzel Michael T. Grice Kyle A. Zingales Sarah K. Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents Heterocyclic Communications bis-chalcone curcumin anti-cancer dynamic nmr dft |
| title | Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents |
| title_full | Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents |
| title_fullStr | Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents |
| title_full_unstemmed | Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents |
| title_short | Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents |
| title_sort | synthesis and conformational analysis of n boc protected 3 5 bis arylidene 4 piperidone ef 24 analogs as anti cancer agents |
| topic | bis-chalcone curcumin anti-cancer dynamic nmr dft |
| url | https://doi.org/10.1515/hc-2022-0162 |
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