5-Phenyl-2-furaldehyde: Synthesis, Reactions and Biological Activities

doi:10.21608/ejchem.2015.978

Cited by 18 publications

(4 citation statements)

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“… Nitrogenous compounds with multiple biological activities, such as antioxidant, anti-diabetic, anti-Alzheimer, and anti-arthritic agents ( Zahoor et al, 2023 , Hammouda et al, 2023 , Zhang et al, 2024 , Abdel-Aziz et al, 2015 , Hashem et al, 2023 ). In addition to our previous studies that highlight the development of various compounds and evaluation of their biological effects as potential drug candidates ( Mukhtar et al, 2021 , Hassan et al, 2015 , Morsy et al, 2021 ). …”

Section: Introductionmentioning

confidence: 90%

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Synthesis, in silico ADMET prediction analysis, and pharmacological evaluation of sulfonamide derivatives tethered with pyrazole or pyridine as anti-diabetic and anti-Alzheimer's agents

Abdelazeem,

Aboulthana,

Hassan

et al. 2024

Saudi Pharmaceutical Journal

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Section: Introductionmentioning

confidence: 90%

“…In addition to our previous studies that highlight the development of various compounds and evaluation of their biological effects as potential drug candidates ( Mukhtar et al, 2021 , Hassan et al, 2015 , Morsy et al, 2021 ).…”

Section: Introductionmentioning

confidence: 90%

Synthesis, in silico ADMET prediction analysis, and pharmacological evaluation of sulfonamide derivatives tethered with pyrazole or pyridine as anti-diabetic and anti-Alzheimer's agents

Abdelazeem,

Aboulthana,

Hassan

et al. 2024

Saudi Pharmaceutical Journal

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“…In view of our previous works (Abd El-All et al, 2016;Ammar et al, 2021;Abdelghany et al, 2021;Elgiushy et al, 2022;Fayed et al, 2021;Hassan, 2021;Hassan et al, 2015Hassan et al, , 2021Hassan et al, , 2022Ibrahim et al, 2021;Mukhtar et al, 2021aMukhtar et al, , 2021bMorsy et al, 2021;Elsherif et al, 2020;Magd-El-Din et al, 2018;Osman et al, 2014) and the abovementioned facts, our work aims to synthesize some of pyrazolo [1,5-a]pyrimidine derivatives 3a-l and 5a-f via the direct cyclo-condensation reaction. Then, the new pyrazolopyrimidine structures were confirmed.…”

Section: Introductionmentioning

confidence: 99%

In vitro enzymatic evaluation of some pyrazolo[1,5‐a]pyrimidine derivatives: Design, synthesis, antioxidant, anti‐diabetic, anti‐Alzheimer, and anti‐arthritic activities with molecular modeling simulation

Hassan

Morsy

Aboulthana

2022

Drug Development Research

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The strategy of utilizing nitrogen compounds in various biological applications has recently emerged as a powerful approach to exploring novel classes of therapeutics to face the challenge of diseases. A series of pyrazolo[1,5‐a]pyrimidine‐based compounds 3a–l and 5a–f were prepared by the direct cyclo‐condensation reaction of 5‐amino‐1H‐pyrazoles 1a, b with 2‐(arylidene)malononitriles and 3‐(dimethylamino)‐1‐aryl‐prop‐2‐en‐1‐ones, respectively. The structures of the new pyrazolo[1,5‐a]pyrimidine compounds were confirmed via spectroscopic techniques. The in vitro biological activities of all pyrazolo[1,5‐a]pyrimidines 3a–l and 5a–f were evaluated by assaying total antioxidant capacity, iron‐reducing power, the scavenging activity against 1‐diphenyl‐2‐picryl‐hydrazyl (DPPH) and 2, 2'‐azinobis‐(3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS) radicals, anti‐diabetic, anti‐Alzheimer, and anti‐arthritic biological activities. All compounds displayed good to potent bioactivity, and three compounds 3g, 3h, and 3l displayed the most active derivatives. Among these derivatives, compound 3l exhibited the highest antioxidant (total antioxidant capacity [TAC] = 83.09 mg gallic acid/g; iron‐reducing power [IRP] = 47.93 µg/ml) and free radicals scavenging activities with (DPPH = 18.77 µg/ml; ABTS = 40.44%) compared with ascorbic acid (DPPH = 4.28 µg/ml; ABTS = 38.84%). Furthermore, compound 3l demonstrated the strongest inhibition of α‐amylase with a percent inhibition of 72.91 ± 0.14 compared to acarbose = 67.92 ± 0.09%. Similarly, it displayed acetylcholinesterase inhibition of 62.80 ± 0.06%. However, compound 3i showed a significantly higher inhibition percentage for protein denaturation and proteinase at 20.66 ± 0.00 and 26.42 ± 0.06%, respectively. Additionally, some in silico ADMET properties were predicted and studied. Finally, molecular docking simulation was performed inside the active site of α‐amylase and acetylcholinesterase to study their interactions.

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“…Based on the aforementioned considerations and in continuation of our research program aimed to develop bioactive candidates, − we have designed and synthesized a series of novel pyrazole–indole hybrids ( 5a – j and 7a – e ) and evaluated their anticancer activity in vitro against four human cancer cells [HCT-116, MCF-7, HepG2, and A549] using the MTT assay. Moreover, the two most potent target compounds ( 7a and 7b ) have been selected to investigate their mechanism of action (cell cycle analysis and apoptosis investigation), enzymatic assays against caspase-3, Bcl-2, Bax, and CDK-2 kinase enzymes.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Anticancer Evaluation, Enzymatic Assays, and a Molecular Modeling Study of Novel Pyrazole–Indole Hybrids

et al. 2021

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The molecular hybridization concept has recently emerged as a powerful approach in drug discovery. A series of novel indole derivatives linked to the pyrazole moiety were designed and developed via a molecular hybridization protocol as antitumor agents. The target compounds ( 5a – j and 7a – e ) were prepared by the reaction of 5-aminopyrazoles ( 1a – e ) with N -substituted isatin ( 4a , b ) and 1 H -indole-3-carbaldehyde ( 6 ), respectively. All products were characterized via several analytical and spectroscopic techniques. Compounds ( 5a – j and 7a – e ) were screened for their cytotoxicity activities in vitro against four human cancer types [human colorectal carcinoma (HCT-116), human breast adenocarcinoma (MCF-7), human liver carcinoma (HepG2), and human lung carcinoma (A549)] using the MTT assay. The obtained results showed that the newly synthesized compounds displayed good-to-excellent antitumor activity. For example, 5-((1 H -indol-3-yl)methyleneamino)- N -phenyl-3-(phenylamino)-1 H -pyrazole-4-carboxamide ( 7a ) and 5-((1 H -indol-3-yl)methyleneamino)-3-(phenylamino)- N -(4-methylphenyl)-1 H -pyrazole-4-carboxamide ( 7b ) provided excellent anticancer inhibition performance against the HepG2 cancer cell line with IC 50 values of 6.1 ± 1.9 and 7.9 ± 1.9 μM, respectively, compared to the standard reference drug, doxorubicin (IC 50 = 24.7 ± 3.2 μM). The two powerful anticancer compounds ( 7a and 7b ) were further subjected to cell cycle analysis and apoptosis investigation in HepG2 using flow cytometry. We have also studied the enzymatic assay of these two compounds against some enzymes, namely, caspase-3, Bcl-2, Bax, and CDK-2. Interestingly, the molecular docking study revealed that compounds 7a and 7b could well embed in the active pocket of the CDK-2 enzyme via different interactions. Overall, the prepared pyrazole–indole hybrids ( 7a and 7b ) can be proposed as strong anticancer candidate drugs against various cancer cell lines.

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5-Phenyl-2-furaldehyde: Synthesis, Reactions and Biological Activities

Abstract: This review article focused on some synthetic methods, reactions and biological activities of 5-phenyl-2-furaldehyde.

Cited by 18 publications

References 56 publications

Synthesis, in silico ADMET prediction analysis, and pharmacological evaluation of sulfonamide derivatives tethered with pyrazole or pyridine as anti-diabetic and anti-Alzheimer's agents

Synthesis, in silico ADMET prediction analysis, and pharmacological evaluation of sulfonamide derivatives tethered with pyrazole or pyridine as anti-diabetic and anti-Alzheimer's agents

In vitro enzymatic evaluation of some pyrazolo[1,5‐a]pyrimidine derivatives: Design, synthesis, antioxidant, anti‐diabetic, anti‐Alzheimer, and anti‐arthritic activities with molecular modeling simulation

Design, Synthesis, Anticancer Evaluation, Enzymatic Assays, and a Molecular Modeling Study of Novel Pyrazole–Indole Hybrids

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