Ultrasound-assisted Synthesis of Some New Curcumin Analogs and Their Corresponding Pyrazoline Derivatives

Hawaiz, Farouq E.; Omer, Dlzhen A. Shekh

doi:10.14500/aro.10149

Cited by 4 publications

(3 citation statements)

References 19 publications

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“…When the same reaction was performed with benzylidene 2 and semicarbazide or thiosemicarbazide in an ethanolic sodium hydroxide (100%), it yielded the dihydropyrazolines 5a and 5b in good yields. It is well known that employing solid NaOH in the reaction condition gives an excellent yield than using NaOH aqueous as a catalyst [38, 39]. The structure of compound 5a was corroborated by spectroscopic data, where its Infrared (IR) spectrum showed bands at 3278, 3204, 1678, and 1587 cm −1 attributed to NH 2 , CO amide, and CN groups, respectively.…”

Section: Resultsmentioning

confidence: 75%

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Maigali

El-Shanawany

El‐Sayed

et al. 2022

Journal of Heterocyclic Chem

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A new series of spiro aryl dioxolane derivatives were synthesized and evaluated to find a new scaffold as potential poly(ADP-ribose)polymerases-1 (PARP-1) inhibitors. This key starting compound, 2,6-bis(methoxybenzylidene)cyclohexanone, was functionalized with different nucleophilic reagents via cyclocondensation reactions to obtain new benzylidene scaffolds containing diverse aryl groups such as spiroindazoleorquinazoline [1,3]dioxolane compounds. Furthermore, the Michael addition reaction of bis-benzylidene with some active methylene compounds afforded spirochromene-or naphthalene-[1,3]dioxolane compounds. All the synthesized compounds revealed promising inhibition with IC 50 values in the nanomolar range (0.997-2.698 nM), not significantly different from that of Olaparib (IC 50 = 0.861 nM). Compounds 5b and 15 (IC 50 = 1.009 and 0.997 nM) showed the highest potency among all the prepared compounds and accordingly their ability to inhibit the growth of BRCA1 mutated breast cancer cell line MDA-MB-436 was tested, where compound 5b (IC 50 = 0.67 μM) showed a potency ten folds higher than that of Olaparib but compound 15 (IC 50 = 7.47 μM) exerted lower activity but still comparable to that of Olaparib (IC 50 = 6.84 μM). Both resulted in the arrest of cell cycle at S phase and caused cell apoptosis. In silico studies including absorption, distribution, metabolism, excretion (ADME) properties, drug-likeness, and molecular docking were carried out to support the above-mentioned findings. This work presents compounds 5b and 15 as promising scaffolds as PARP-1 inhibitors. | INTRODUCTIONPoly(ADP-ribose) polymerases (PARPs) comprise a family of adenosine diphosphate ribosyltransferases (ADPribosyltransferases) found in all six major eukaryotic supergroups, as well as several species of prokaryotes and dsDNA virus. This family comprises 18 members that are implicated in different processes on the cellular level such as controlling genome integrity and checkpoints for the cell cycle and also have a role in the signaling pathways of DNA repair, transcription, and apoptosis. PARP proteins transfer ADP-ribose moieties to arginine, glutamate, aspartate, cysteine, lysine, and serine acceptor sites [1][2][3][4].The most abundant and well-known member is PARP-1, due to its important role in DNA damage

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Section: Resultsmentioning

confidence: 75%

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Maigali

El-Shanawany

El‐Sayed

et al. 2022

Journal of Heterocyclic Chem

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“…Senyawa ini disintesis dengan bahan dasar turunan benzaldehida dan keton menggunakan katalis KOH 5% melalui metode refluks dalam waktu 50 menit. (Hawaiz dan Shekh Omer, 2017) menggunakan metode ultrasound untuk mensintesis senyawa analog kurkumin karena lebih efisien, memerlukan waktu yang lebih singkat, tanpa ekstra temperature dan rendemen yang dihasilkan relatif lebih tinggi. Hasil penelitian (Anisa dkk., 2020) juga memperlihatkan bahwa sintesis senyawa analog kurkumin dari 3,4-benzaldehida dan siklopentanon dengan katalis KOH 5% hasilnya lebih efisien, murah, cepat, dengan rendemen yang lebih tinggi sebesar 85,71% menggunakan metode ultrasound dibandingkan dengan metode konvensional.…”

Section: Gambar 1 Struktur Molekul Kurkuminunclassified

Sintesis Senyawa Analog Kurkumin Monoketon Dengan Variasi Konsentrasi Katalis Koh

Anisa

Utami²,

Hidayat³

2022

Analit Anal. Environ. Chem.

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Kurkumin adalah salah satu bahan aktif dalam kunyit (Curcuma longa) dan telah mendapat perhatian karena sifat biologisnya dalam pengobatan penyakit kronis. Kurkumin mempunyai bioavailabilitas yang rendah dan metabolisme yang cepat namun senyawa analog kurkumin menunjukkan bioavailabilitas yang lebih baik. Penelitian ini bertujuan untuk mensintesis senyawa analog kurkumin serta menentukan variasi konsentrasi katalis yang mendapatkan rendemen tertinggi. Senyawa analog kurkumin monoketon telah disintesis menggunakan reaksi kondensasi Claisen Smidht dengan katalis KOH. Sintesis dilakukan dengan menggunakan metode ultrasound pada suhu kamar dalam waktu 30 menit. Pelarut yang digunakan ialah n-heksan : etil asetat (1 : 1). Sintesis senyawa analog kurkumin monoketon dengan katalis KOH menggunakan konsentrasi yang divariasikan dari 2,5 %; 5%; 7,5%; dan 10% memperoleh rendemen 81,4%; 58,64%; 57,11% dan 58,60%. Hasil sintesis diidentifikasi menggunakan FTIR. Kesimpulan dari penelitian ini menunjukkan bahwa variasi konsetrasi KOH dengan persentase 2,5% menunjukkan rendemen tertinggi sebesar 81,4%.Kata kunci: katalis, senyawa analog kurkumin, ultrasound.

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“…Previous work reports the efficacy of ultrasonication in enhancing the yield of curcumin and its analogs, suggesting its potential for optimizing EHP synthesis. Studies have reported substantial increases in yield with prolonged ultrasonic extraction times, further underscoring the promise of this method [8,9]. Moreover, the application of ultrasonication in condensation reactions has yielded high yields of curcumin analogs, displaying its versatility and effectiveness in synthetic chemistry [10,11].…”

Section: Introductionmentioning

confidence: 98%

Ultrasonic Assisted Synthesis of 1,5-Bis(3'-ethoxy-4'-hydroxyphenyl)-1,4-pentadiene-3-one: Effect of Time and Temperature

Mulatsari,

Mumpuni,

Purwanggana

et al. 2024

ajc

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The compound 1,5-bis(3′-ethoxy-4′-hydroxyphenyl)-1,4-pentadiene-3-one (EHP), an analog of curcumin, displays significant antioxidant, anti-inflammatory and antibacterial properties. Synthesized through an aldol condensation reaction, EHP modifies the structure of curcumin by substituting methoxy groups with ethoxy groups and converting diketones to monoketone. This study explores the influence of time and temperature on the ultrasonic-assisted synthesis of 1,5-bis(3′-ethoxy-4′-hydroxyphenyl)-1,4-pentadiene-3-one (EHP). The synthesis process involved precise measurements and controlled conditions to achieve the desired compound. Through a series of experiments conducted at varying temperatures and irradiation times, the synthesis yield and purity of EHP were evaluated. Analysis techniques including thin layer chromatography (TLC), densitometry, ultraviolet-visible (UV-vis) spectrophotometry, Fourier-transform infrared spectroscopy (FTIR), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy were employed to characterize the EHP compound. The results indicate the sensitivity of EHP synthesis to reaction conditions, it reduce synthesis time (10 min) with improve the product yield (87.17%) at moderate temperature (30 ºC). The findings provide valuable insights into optimizing synthesis conditions for enhanced product quality.

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Ultrasound-assisted Synthesis of Some New Curcumin Analogs and Their Corresponding Pyrazoline Derivatives

Cited by 4 publications

References 19 publications

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Sintesis Senyawa Analog Kurkumin Monoketon Dengan Variasi Konsentrasi Katalis Koh

Ultrasonic Assisted Synthesis of 1,5-Bis(3'-ethoxy-4'-hydroxyphenyl)-1,4-pentadiene-3-one: Effect of Time and Temperature

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