Synthesis and Toxicity Assessments Some Para-methoxy Chalcones Derivatives

Perdana, Fitra; Eryanti, Yum; Zamri, Adel

doi:10.1016/j.proche.2015.12.040

Cited by 10 publications

(8 citation statements)

References 18 publications

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“…The toxicological scrutiny of the compounds is important to drive a decision for a novel chemical entity to be used as a therapeutic drug in practical applications [135]. So far, extensive research on efficacy, safety, and pharmacokinetics profile of natural and synthetic chalcones have been reported [136]. Physicochemical potency toxicity profiles showed that chalcones followed the Lipinski rule of five (requisite parameters for druggability) with 91.91% oral absorption values [137].…”

Section: A C C E P T Ementioning

confidence: 99%

Activation of Nrf2 signaling pathway by natural and synthetic chalcones: a therapeutic road map for oxidative stress

Egbujor

Saha²,

Buttari³

et al. 2021

Expert Review of Clinical Pharmacology

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Introduction:Nuclear factor erythroid 2-related factor 2 (Nrf2) signaling pathway plays a key role in diverse gene expressions responsible for protection against oxidative stress and xenobiotics. Chalcones with a common chemical scaffold of 1,3-diaryl-2propen-1-one, are abundantly present in nature with a wide variety of pharmacological properties. This review will discuss the interactions of natural and synthetic chalcones with Nrf2 signaling. Areas covered:Chalcones are reportedly found to activate Nrf2 signaling pathway, expression of Nrf2-regulated antioxidant genes, induce cytoprotective proteins and upregulate multidrug resistance-associated proteins. Chalcones being soft electrophiles are less prone to hostile off-target effects and unlikely to induce carcinogenicity and mutagenicity. Furthermore, their low toxicity, structural diversity, feasibility in structural reorganization and the presence of α,ß-unsaturated carbonyl group which makes them suitable drug candidates targeting Nrf2-dependent diseases. Expert opinion:Nrf2-Keap1 signaling pathway plays a central role in redox signaling. However, available therapeutic agents for Nrf2 activation have limited practical applications due to their associated risks, relatively low efficacy and bioavailability. The designing and fabrication of new chemical entities with chalcone scaffold-based Michael acceptor mechanism should be aimed as potential therapeutic Nrf2 activators to target oxidative stress and inflammation-mediated diseases such as atherosclerosis, Alzheimer's disease, Parkinson's disease and many more.

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Section: A C C E P T Ementioning

confidence: 99%

Activation of Nrf2 signaling pathway by natural and synthetic chalcones: a therapeutic road map for oxidative stress

Egbujor

Saha²,

Buttari³

et al. 2021

Expert Review of Clinical Pharmacology

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“…Some chalcone compounds have been tested against BSLT. Perdana et al (2015) synthesized anti-cancer derivatives of methoxychalcones, which were produced from the reaction of 4-methoxy acetophenone and aromatic aldehyde derivatives. Consequently, three para methoxychalcones compounds showed safety, as evidenced by the LC50 value <200µg / mL using the BSLT method (Perdana et al, 2015).…”

Section: Histopathological Studiesmentioning

confidence: 99%

“…Perdana et al (2015) synthesized anti-cancer derivatives of methoxychalcones, which were produced from the reaction of 4-methoxy acetophenone and aromatic aldehyde derivatives. Consequently, three para methoxychalcones compounds showed safety, as evidenced by the LC50 value <200µg / mL using the BSLT method (Perdana et al, 2015). In this study, acute toxicity of DPP is at category 5 according to the Globally Harmonized Classification System.…”

Section: Histopathological Studiesmentioning

confidence: 99%

Toxicity Study of 1-(2, 5-Dihidroxyphenil)-3-Pyridine-2-Il-Propenone In Adult Female Mice

et al. 2021

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This research aimed to evaluate the toxicity of 1-(2, 5-dihidroxyphenil)-3-pyridine-2-il-propenone (DPP) after 24 hours and 90-day administration in female mice. Acute toxicity test was performed using the OECD 423 method, and DPP was administered once a day at doses of 300, 2000, and 5000 mg/kg body weight (BW). Toxic symptoms were observed after 24 hours of administration, and this continued until the 14th day. The experimental animals were dissected and examined for histological organs on the 15th day. The sub-chronic toxicity test was performed using the OECD 408 method, and DPP at 14, 28, and 56 mg/kg/day was administered for 90 days. Toxic symptoms were observed every day, and the amount of food and water intakes were also measured. Furthermore, statistical analysis was performed, and changes in body weight as well as routine blood checks and biochemistry were observed. At the end of the study, experimental animals were killed and the vital organs' weights were examined before their histological analysis. The results showed that DPP at 300-5000 mg/kg/day and 14-56 mg/kg/day for 90 days did not show any toxic symptom respectively. In the sub-chronic toxicity test, no change was observed in blood and urine biochemical parameters (p≥0.05). However, lymphocytic infiltration in the liver and congested vessel in the kidney occurred after administration at 56 mg/kg / day. The results showed that the acute toxicity of DPP is at category 5 according to Globally Harmonized Classification System and sub-chronic toxicity is at a dose below 56 mg/kg/day.

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“…Kalkon merupakan salah satu senyawa metabolit sekunder golongan flavonoid rantai terbuka dengan dua cincin aromatik yang digabungkan dengan sistem tiga atom karbon karbonil α, β-tak jenuh. Senyawa kalkon merupakan prekursor penting pada proses biosintesis dari flavonoid, isoflavonoid, dan beberapa senyawa heterosiklik (Perdana et al, 2015). Beberapa senyawa kalkon dapat ditemukan di alam, namun penyebaran senyawa kalkon di alam sangat terbatas dan hanya ditemukan pada beberapa golongan tumbuhan dalam jumlah yang sedikit.…”

Section: Pendahuluanunclassified

Sintesis 3,4,4’-Trimetoksikalkon dan Karakterisasinya

Rehana

Fahreza

2019

ALCHEMY J.Pen.Kim

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Senyawa 3,4,4’-trimetoksikalkon dapat disintesis dari 4-metoksi asetofenon dan 3,4-dimetoksi benzaldehid melalui reaksi Claisen-Schmidt. Reaksi Claisen-Schmidt dipengaruhi jumlah katalis basa dan lama reaksi. Penelitian ini bertujuan untuk mengetahui variasi waktu reaksi dan jumlah NaOH terhadap rendemen 3,4,4’-trimetoksikalkon. Penelitian ini meliputi sintesis 10 mmol 3,4,4’-trimetoksikalkon dari 10 mmol 4-metoksi asetofenon dan 3,4-dimetoksi benzaldehid dengan jumlah katalis NaOH 2, 4, 8, 12, 16 dan 20 mmol dengan waktu reaksi pembentukan enolat 1, 2, 3, 4 dan 5 jam. Hasil sintesis diuji kemuriannya dengan Kromatografi Lapis Tipis (KLT) dan titik lebur kemudian dikarakterisasi dengan spektrofotometri UV-visible dan Nuclear Magnetic Resonance (NMR). Peningkatan konsentrasi NaOH dari 2, 4 dan 8 mmol meningkatkan rendemen hasil sintesis dari 60,06%; 62,60% dan 80,19%, tetapi penambahan NaOH di atas 8 mmol menurunkan rendemen. Peningkatan waktu reaksi dari 1, 2 dan 3 jam meningkatkan rendemen dari 74,20%; 78,61% dan 87,66 %, tetapi penambahan waktu 4 dan 5 jam menurunkan rendemen. Analisis KLT menunjukkan bahwa hasil sintesis murni dengan titik lebur 82 – 85 oC. Karakterisasi menggunakan UV-visibel dan NMR menunjukkan senyawa hasil sintesis adalah 3,4,4’-trimetoksikalkon. Konsentrasi NaOH dan lama waktu reaksi pembentukan enolat mempengaruhi rendemen sintesis 3,4,4’-trimetoksikalkon dengan rendemen terbesar menggunakan katalis NaOH 8 mmol dengan waktu reaksi pembentukan enolat selama 3 jam.

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Synthesis and Toxicity Assessments Some Para-methoxy Chalcones Derivatives

Cited by 10 publications

References 18 publications

Activation of Nrf2 signaling pathway by natural and synthetic chalcones: a therapeutic road map for oxidative stress

Activation of Nrf2 signaling pathway by natural and synthetic chalcones: a therapeutic road map for oxidative stress

Toxicity Study of 1-(2, 5-Dihidroxyphenil)-3-Pyridine-2-Il-Propenone In Adult Female Mice

Sintesis 3,4,4’-Trimetoksikalkon dan Karakterisasinya

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