Direct Amidation of ethyl p-methoxycinnamate to Produce N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide

Komala, Ismiarni; Supandi, Supandi; Hardiansyah, Muhammad Mirza

doi:10.15408/jkv.v4i1.7300

Cited by 4 publications

(4 citation statements)

References 11 publications

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“…Compound 5 was obtained as a white amorphous with the melting point of 132-135 o C. Analysis of the MS data of GCMS indicated the presence of a molecular ion peak [M] + at 205 m/z, which is correlated to the molecular formula of C12H15NO2. The base peak is found at m/z 161, which is typical of the presence of a pmethoxycinnamate moiety (Komala, Supandi, & Hardiansyah, 2018). This peak occurs due to the loss of the -N(CH3)2 from the whole structure of compound 5 (Figure 5).…”

Section: Resultsmentioning

confidence: 99%

An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity

et al. 2020

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Ethyl p-methoxycinnamate (EPMC) (1) is a major natural ester found in the rhizome of Kaempferia galanga and has been reported to have anti-inflammatory activity. Some of the structural modification of this compound has been carried out in order to study the structure-activity relationship on its anti-inflammatory activity. In the present study, we report a new, simple and efficient procedure in the conversion of the ethyl p-methoxycinnamate into N,N-dimethyl-p-methoxycinnamamide (5) and then study the structure-activity relationship on its anti-inflammatory activity. The reaction was carried out through a microwave-assisted direct amidation between (EPMC) (1) with dimethylformamide (DMF) in the basic condition. The mixture was irradiated by using unmodified microwave-oven at 300 W for 1 minute to obtain compound (5) in 88.8% yields. The extensive analysis of the GCMS and NMR data supported that the product of synthesis is N,N-dimethyl-p-methoxycinnamamide (5). Evaluation of the anti-inflammatory activity of compound 5 by using anti-denaturation of heat bovine serum albumin (BSA) assay indicated that N,N-dimethyl-p-methoxycinnamamide (5) still have anti-denaturation activity. Compound 5 has an amide functional group which is more slowly hydrolyzed if compared to 1. Hence, the reaction has successfully produced a more stable compound which still has anti-inflammatory activity

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Section: Resultsmentioning

confidence: 99%

An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity

et al. 2020

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“…According to the MS data of GCMS, the molecular weight of 5b is 190, which corresponds to the molecular formula of C12H14O2. A prominent peak appears at m/z 161, indicating the loss of C2H5 from the structure, where a peak at m/z 161 usually suggests the presence of p-methoxylcinnamic moiety in the structure [26]. The 1 H-NMR spectrum exhibited the presence of four integrated protons at  6.91 (2H, d, J = 9 Hz, 2CH-Ar), 7.50 (2H, d, J = 9, 2CH-Ar), two trans-coupled peaks at 6.63 (1H, d, J = 16 Hz, =CH) and 7.52 (1H, d, J = 16 Hz, =CH), three integrated protons at  3.86 (3H, s, OCH3), indicating the presence of p-methoxy cinnamic acid moiety [26].…”

Section: Resultsmentioning

confidence: 99%

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

Komala

Supandi

Nurmeilis

et al. 2021

J. Math. Fund. Sci.

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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.

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“…Jamu beras kencur yang mengandung rimpang kencur sebagai bahan utamanya telah dipercaya oleh masyarakat Indonesia mampu meningkatkan nafsu makan dan dapat meredakan rasa nyeri otot dan pegal linu (Komala, Supandi and Hardiansyah, 2018).…”

Section: Pendahuluanunclassified

Pengembangan dan Evaluasi Stabilitas Formulasi Gel yang Mengandung Etil p-metoksisinamat

Suryani¹,

Mubarika²,

Komala³

2019

Pharm.biomed.Sci.J

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Etil p-metoksisinamat (EPMS) merupakan senyawa utama aktif anti-inflamasi yang terdapat dalam rimpang kencur (Kaempferia galanga). Tujuan penelitian ini adalah untuk mengembangkan sediaan gel yang mengandung EPMS dengan menggunakan kombinasi HPMC dan karbopol 940 sebagai gelling agent. Sediaan gel di buat dalam tiga formula F1, F2 dan F3 dengan variasi persentase kombinasi HPMC : karbopol 940 yang digunakan masing-masingnya adalah 0,4 : 0,4%, 0,5 : 0,5%, dan 1.0 : 0,5%. Masing-masing formula selanjutnya dievaluasi sifat fisik dan kimianya. Hasil evaluasi fisik menunjukkan bahwa secara organoleptis ketiga formula F1, F2 dan F3 memenuhi syarat sediaan gel, serta stabil ketika dilakukan pengujian sentrifugasi dan cycling test. Formuala F2 merupakan sediaan terbaik dalam pembuatan sediaan gel EPMS. Evaluasi stabilitas kimia menunjukkan bahwa kadar EPMS dalam sediaan gel hari ke- 0, 7, 14, dan 21 berada dalam rentang 91–100%. Sediaan gel mengalami penurunan kadar EPMS masing-masingnya sebesar 9% (F1), 5% (F2) dan 6%, (F3).

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Direct Amidation of ethyl p-methoxycinnamate to Produce N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide

Cited by 4 publications

References 11 publications

An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity

An Efficient Directly Conversion of the Ethyl p-Methoxycinnamate into N,N-dimethyl-p-Methoxycinnamamide and study the structure-activity relationship on anti-inflammatory activity

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

Pengembangan dan Evaluasi Stabilitas Formulasi Gel yang Mengandung Etil p-metoksisinamat

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