Development trans-N-benzyl hydroxyl cinnamamide based compounds from cinnamic acids and characteristics anticancer potency

Zenta, Firdaus; Soekamto, Nunuk Hariani; Dali, Seniwati; Firdausiah, Syadza; Rasyid, Herlina; Bahriah, Bahriah; Agustan, Agustan; Tahir, Dahlang

doi:10.1007/s13738-022-02499-7

Cited by 4 publications

(2 citation statements)

References 36 publications

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“…The two most abundant compounds in the aromatic ginger essential oil were trans-ethyl-pmethoxycinnamate and trans-ethyl cinnamate [1][2]5]. Ethyl-p-methoxycinnamate and its derivatives had many benefits, including as anticancer [6][7][8], anti-inflammatory [9][10], anti-tuberculosis [11], anti-neoplastic [12], antimicrobe [13], and antidiabetic [14] agents. The study of K. galanga L. extract as an antidiabetic using the Gavage method every day for one month found that diabetic rats before and after treatment with K. galanga L. extract showed a significant difference in reducing the amount of blood glucose [15].…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of N-phenethyl-p-methoxycinnamamide and N-morpholinyl-p-methoxycinnamamide, In Vitro and In Silico Study as α-Glucosidase Inhibitor

Rasyid

Firdaus²,

Firdausiah³

et al. 2022

Indones. J. Chem.

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Aromatic ginger (Kaempferia galanga L.) is one of the natural sources containing ethyl-p-methoxycinnamate, which is known to have beneficial activity, especially as an α-glucosidase inhibitor. This study aims to convert ethyl-p-methoxycinnamate into amide form as N-phenethyl-p-methoxycinnamamide (4a) and N-morpholinyl-p-methoxycinnamamide (4b) through some synthetic ways then tested their activity as an α-glucosidase inhibitor. The FTIR spectra of 4a present a short single peak at 3269.34 cm−1 that belongs to the N-H group, while spectra of 4b show no absorption band between 3200–3400 cm−1 due to its tertiary amide structure. Spectroscopy analysis through 1H- and 13C-NMR exhibits the successful synthesis of both compounds. Bioactivity test results show that compound 4b has better activity than 4a. In molecular dynamics simulation, the binding energy of compounds 4a and 4b reveal that both compounds have a similar binding energy of about -98980.8 and -97696.7 kJ mol−1, respectively.

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Section: ■ Introductionmentioning

confidence: 99%

Synthesis of N-phenethyl-p-methoxycinnamamide and N-morpholinyl-p-methoxycinnamamide, In Vitro and In Silico Study as α-Glucosidase Inhibitor

Rasyid

Firdaus²,

Firdausiah³

et al. 2022

Indones. J. Chem.

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“…The reported synthesis of cinnamamide derivatives mostly utilizes thionyl chloride [14,18,19], which is one of the chemicals included in the Chemical Weapon Convention list [20]. Alternatively, amide synthesis can be achieved using 1,1'-carbonyldiimidazole (CDI) [21,22], but the intermediate formed is less reactive than the acyl chloride [23].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and α-glucosidase inhibitory activity of cinnnamamides

Aijijiyah

Wati

Rahayu

et al. 2022

Preprint

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Suitably substituted cinnnamamides were successfully synthesized in 11-92% yield. Majority of the cinnnamamides displayed IC50 greater than acarbose. Their α-glucosidase inhibitory activity greatly depended on their structure with electron-withdrawing groups on the cinnamoyl aromatic ring causing increased inhibition activity. The synthesized cinnnamamides showed acceptable physicochemical and pharmacokinetics characteristics with little toxicity indicating their potential use as lead drug candidates. Molecular docking studies of these compounds were also conducted to elucidate their mechanism of action. Overall, these cinnnamamides show potential as lead structures for further optimization as α-glucosidase inhibitors.

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Synthesis, α-glucosidase inhibitory activity, and molecular docking of cinnamamides

et al. 2023

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Development trans-N-benzyl hydroxyl cinnamamide based compounds from cinnamic acids and characteristics anticancer potency

Cited by 4 publications

References 36 publications

Synthesis of <i>N</i>-phenethyl-<i>p</i>-methoxycinnamamide and <i>N</i>-morpholinyl-<i>p</i>-methoxycinnamamide, <i>In Vitro</i> and <i>In Silico</i> Study as α-Glucosidase Inhibitor

Synthesis of <i>N</i>-phenethyl-<i>p</i>-methoxycinnamamide and <i>N</i>-morpholinyl-<i>p</i>-methoxycinnamamide, <i>In Vitro</i> and <i>In Silico</i> Study as α-Glucosidase Inhibitor

Synthesis and α-glucosidase inhibitory activity of cinnnamamides

Synthesis, α-glucosidase inhibitory activity, and molecular docking of cinnamamides

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