Microwave-Assisted Claisen-Schmidt Condensation Reaction of Ethyl p-methoxycinnamate to Synthesize p-Methoxystyryl Ketone Derivatives and Evaluate Anti-inflammatory Activity of Synthetic Products
| Autor: | Ghilman Dharmawan, Moethia Moethia, Ofa Suzanti Betha, Ismiarni Komala, Muhamad Beny Setiawan, Putri Hayati Nufus, Noni Tri Utami, Nurmeilis Nurmeilis, Nurkhyati Putri Indriyani, Supandi Supandi, Yardi Yardi |
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| Rok vydání: | 2021 |
| Předmět: |
(E)-4-(4-methoxyphenyl)but-3-en-2-one
Ketone Science (General) medicine.drug_class Science General Mathematics General Physics and Astronomy Claisen schmidt condensation Microwave assisted Anti-inflammatory General Biochemistry Genetics and Molecular Biology Q1-390 (E)-1-(4-methoxyphenyl)pent-1-en-3-one medicine Organic chemistry Claisen-Schmidt condensation (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one chemistry.chemical_classification Multidisciplinary Chemistry General Chemistry General Medicine Ethyl p-methoxycinnamate General Earth and Planetary Sciences General Agricultural and Biological Sciences |
| Zdroj: | Journal of Mathematical and Fundamental Sciences, Vol 53, Iss 1 (2021) |
| ISSN: | 2338-5510 2337-5760 |
| DOI: | 10.5614/j.math.fund.sci.2021.53.1.6 |
| Popis: | The rhizome of Kaempferia galanga has been known to contain ethyl p-methoxycinnamate (EPMC) (1) as a main component, which has anti-inflammatory properties. Previously we have reported the structural modification of EPMC (1) to form another ester, nitrostyrene, and cinnammamide derivatives and then studied their structure-activity relationships as anti-inflammatory agent. In continuing our research, in this paper, we report the microwave-assisted Claisen-Schmidt condensation of EPMC (1) to synthesize a series of p-methoxystyryl ketones followed by a study of their anti-inflammatory activity. The reaction begins with microwave-assisted cleavage oxidation of hydrolyzed product of EPMC, p-methoxycinnamic acid (2) with Ca(NO3)2 for the synthesis of p-methoxybenzaldehyde (3). Furthermore, 3 was reacted with acetophenone, ethyl methyl ketone and acetone via microwave-assisted Claisen-Schmidt condensation for the synthesis of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (5a) (E)-1-(4-methoxyphenyl)pent-1-en-3-one (5b) and (E)-4-(4-methoxyphenyl)but-3-en-2-one (5c), respectively. The reaction products were characterized using spectroscopic techniques and were then tested for anti-inflammatory activity using in vitro anti-denaturation of protein assay. It was found that converting EPMC (1) to 5a and 5b reduced anti-inflammatory activity, while 5c retained anti-denaturation activity with an IC50 of 72.8 µg/ml. |
| Databáze: | OpenAIRE |
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