Microwave-Assisted Claisen-Schmidt Condensation Reaction of Ethyl p-methoxycinnamate to Synthesize p-Methoxystyryl Ketone Derivatives and Evaluate Anti-inflammatory Activity of Synthetic Products

Authors

  • Ismiarni Komala Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Supandi Supandi Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Nurmeilis Nurmeilis Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Yardi Yardi Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Ofa Suzanti Betha Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Nurkhyati Putri Indriyani Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Moethia Moethia Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No , Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Muhamad Beny Setiawan Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Ghilman Dharmawan Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No , Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Putri Hayati Nufus Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia
  • Noni Tri Utami Pharmacy Department, Faculty of Health Sciences, Universitas Islam Negeri Syarif Hidayatullah Jakarta, Indonesia. Jl. Kertamukti No 5, Pisangan Ciputat 15419 Tangerang Selatan, Banten Indonesia

DOI:

https://doi.org/10.5614/j.math.fund.sci.2021.53.1.6

Keywords:

Claisen-Schmidt condensation, (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one, (E)-1-(4-methoxyphenyl)pent-1-en-3-one, (E)-4-(4-methoxyphenyl)but-3-en-2-one

Abstract

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 g/ml.

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Published

2021-06-07

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