Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential Antimalarials
New protocol for the preparation of the novel caffeic acid derivatives using the Wittig reaction has been applied to follow the principles of green chemistry. The compounds have been evaluated against chloroquine-sensitive and chloroquine-resistant P. falciparum strains. Their cytotoxicity to normal...
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| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Wiley
2023-01-01
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| Series: | Journal of Parasitology Research |
| Online Access: | http://dx.doi.org/10.1155/2023/6675081 |
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| author | Katarzyna Sidoryk Silvia Parapini Nicoletta Basilico Magdalena Zaremba-Czogalla Marek Kubiszewski Marcin Cybulski Jerzy Gubernator Agnieszka Zagórska Anna Jaromin |
| author_facet | Katarzyna Sidoryk Silvia Parapini Nicoletta Basilico Magdalena Zaremba-Czogalla Marek Kubiszewski Marcin Cybulski Jerzy Gubernator Agnieszka Zagórska Anna Jaromin |
| author_sort | Katarzyna Sidoryk |
| collection | DOAJ |
| description | New protocol for the preparation of the novel caffeic acid derivatives using the Wittig reaction has been applied to follow the principles of green chemistry. The compounds have been evaluated against chloroquine-sensitive and chloroquine-resistant P. falciparum strains. Their cytotoxicity to normal human dermal fibroblasts and their propensity to induce hemolysis have been also determined. Ethyl (2E)-3-(2,3,4-trihydroxyphenyl)-2-methylpropenoate has exhibited the highest antiplasmodial activity against P. falciparum strains without the cytotoxic and hemolytic effects. This derivative is significantly more potent than caffeic acid parent structure. The application of our one-step procedure has been shown to be rapid and efficient. It allows for an easy increase of input data to refine the structure-activity relationship model of caffeates as the antimalarials. The one-step approach meets the conditions of “atom economy” and eliminates hazardous materials. Water has been used as the effective medium for the Wittig reaction to avoid toxic organic solvents. |
| format | Article |
| id | doaj-art-02de833a697a4bdd82cdc523d373951c |
| institution | Kabale University |
| issn | 2090-0031 |
| language | English |
| publishDate | 2023-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Parasitology Research |
| spelling | doaj-art-02de833a697a4bdd82cdc523d373951c2025-02-03T06:45:12ZengWileyJournal of Parasitology Research2090-00312023-01-01202310.1155/2023/6675081Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential AntimalarialsKatarzyna Sidoryk0Silvia Parapini1Nicoletta Basilico2Magdalena Zaremba-Czogalla3Marek Kubiszewski4Marcin Cybulski5Jerzy Gubernator6Agnieszka Zagórska7Anna Jaromin8PharmacyDipartimento di Scienze Biomediche per la SaluteDipartimento di Scienze BiomedicheDepartment of Lipids and LiposomesPharmaceutical Analysis LaboratoryPharmacyDepartment of Lipids and LiposomesDepartment of Medicinal ChemistryDepartment of Lipids and LiposomesNew protocol for the preparation of the novel caffeic acid derivatives using the Wittig reaction has been applied to follow the principles of green chemistry. The compounds have been evaluated against chloroquine-sensitive and chloroquine-resistant P. falciparum strains. Their cytotoxicity to normal human dermal fibroblasts and their propensity to induce hemolysis have been also determined. Ethyl (2E)-3-(2,3,4-trihydroxyphenyl)-2-methylpropenoate has exhibited the highest antiplasmodial activity against P. falciparum strains without the cytotoxic and hemolytic effects. This derivative is significantly more potent than caffeic acid parent structure. The application of our one-step procedure has been shown to be rapid and efficient. It allows for an easy increase of input data to refine the structure-activity relationship model of caffeates as the antimalarials. The one-step approach meets the conditions of “atom economy” and eliminates hazardous materials. Water has been used as the effective medium for the Wittig reaction to avoid toxic organic solvents.http://dx.doi.org/10.1155/2023/6675081 |
| spellingShingle | Katarzyna Sidoryk Silvia Parapini Nicoletta Basilico Magdalena Zaremba-Czogalla Marek Kubiszewski Marcin Cybulski Jerzy Gubernator Agnieszka Zagórska Anna Jaromin Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential Antimalarials Journal of Parasitology Research |
| title | Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential Antimalarials |
| title_full | Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential Antimalarials |
| title_fullStr | Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential Antimalarials |
| title_full_unstemmed | Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential Antimalarials |
| title_short | Efficient One-Pot Synthesis of Novel Caffeic Acid Derivatives as Potential Antimalarials |
| title_sort | efficient one pot synthesis of novel caffeic acid derivatives as potential antimalarials |
| url | http://dx.doi.org/10.1155/2023/6675081 |
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