Ultrasonic-induced synthesis of novel diverse arylidenes <i>via</i> Knoevenagel condensation reaction. Antitumor, QSAR, docking and DFT assessment

El-Sayed Ebead, Eman; Aboelnaga, Asmaa; Nassar, Ekhlass; Naguib, Mohamed M.; Ismail, Mahmoud F.

doi:10.1039/d3ra05799b

RSC Adv.

2023

DOI: 10.1039/d3ra05799b

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Ultrasonic-induced synthesis of novel diverse arylidenes via Knoevenagel condensation reaction. Antitumor, QSAR, docking and DFT assessment

Eman El-Sayed Ebead,

Asmaa Aboelnaga,

Ekhlass Nassar

et al.

Abstract: A series of arylidenes derivatives was synthesized under ultrasonic methodology via Knoevenagel condensation reaction of cyanoacetohydrazide derivative with the appropriate aldehydes and/or ketone.

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2024

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Cited by 5 publications

References 87 publications

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Pharmacophore‐based, rationale design, and efficient synthesis of novel tetrahydrobenzo[b]thiophene candidates as potential dual Topo I/II inhibitors and DNA intercalators

Nofal,

Al‐Karmalawy,

Elmaaty

et al. 2024

Archiv der Pharmazie

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A series of tetrahydrobenzo[b]thiophene derivatives was designed and synthesized as dual topoisomerase (Topo) I/II inhibitors implicating potential DNA intercalation. Ethyl‐2‐amino‐3‐cyano‐4,5,6,7‐tetrahydrobenzo[b]thiophene‐4‐carboxylate (1) was prepared by modification of the Gewald reaction procedure using a Fe2O3 nanocatalyst and then it was used as a building block for the synthesis of tetrahydrobenzo[b]thiophene candidates (2–14). Interestingly, compound 14 showed the best cytotoxic potential against hepatocellular, colorectal, and breast cancer cell lines (IC50 = 7.79, 8.10, and 3.53 µM), respectively, surpassing doxorubicin at breast cancer (IC50 = 4.17 µM). Meanwhile, the Topo I and II inhibition assay displayed that compound 3 could exhibit the best inhibitory potential among the investigated candidates (IC50 = 25.26 and 10.01 nM), respectively, in comparison to camptothecin (IC50 = 28.34 nM) and doxorubicin (IC50 = 11.01 nM), as reference standards. In addition, the DNA intercalation assay showed that compound 14 could display the best binding affinity with an IC50 value of 77.82 µM in comparison to doxorubicin (IC50 = 58.03 µM). Furthermore, cell cycle and apoptosis analyses described that compound 3 prompts the G1 phase arrest in michigan cancer foundation‐7 cancer cells and increases the apoptosis ratio by 29.31% with respect to untreated cells (2.25%). Additionally, the conducted molecular docking assured the promising binding of the investigated members toward Topo I and II with potential DNA intercalation. Accordingly, the synthesized compounds could be treated as promising anticancer candidates for future optimization.

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Pharmacophore‐based, rationale design, and efficient synthesis of novel tetrahydrobenzo[b]thiophene candidates as potential dual Topo I/II inhibitors and DNA intercalators

Nofal,

Al‐Karmalawy,

Elmaaty

et al. 2024

Archiv der Pharmazie

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Synthesis and evaluation of larvicidal efficacy against C. pipiens of some new heterocyclic compounds emanated from 2‐cyano‐N′‐(2‐(2,4‐dichlorophenoxy)acetyl)acetohydrazide

Ismail,

El‐Sayed,

Hosni

et al. 2024

Chemistry & Biodiversity

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Several infectious diseases are transmitted and spread by mosquitoes, and millions of people die annually from them. The mosquito, Culex pipiens is a responsible for the emergence of various Virus in Egypt. So, we devote our work to evaluate the larvicidal efficacy against C. pipiens of some new heterocyclic compounds containing chlorine motifs. The implementation was emanated from using 2‐cyano‐N′‐(2‐(2,4‐dichlorophenoxy)acetyl)acetohydrazide (3) as scaffold to synthesize some new heterocyclic compounds. The structures of the synthesized compounds were interpreted scrupulously by spectroscopic and elemental analyses. Thereafter, the larvicidal activity against C. pipiens of thirteen synthesized compounds was estimated. Noteworthy, cyanoacetohydrazide derivative 3 and 3‐iminobenzochromene derivative 12 showed a fabulous potent efficacy with LC50 equal to 3.2 and 3.5 ppm against C. pipiens, respectively, and are worth being further evaluated in the field of pest control.

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Efficient synthesis and molecular docking analysis of quinazoline and azole hybrid derivatives as promising agents for anti-cancer and anti-tuberculosis activities

Kumar,

Soni

et al. 2024

Journal of Molecular Structure

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Ultrasonic-induced synthesis of novel diverse arylidenes via Knoevenagel condensation reaction. Antitumor, QSAR, docking and DFT assessment

Abstract: A series of arylidenes derivatives was synthesized under ultrasonic methodology via Knoevenagel condensation reaction of cyanoacetohydrazide derivative with the appropriate aldehydes and/or ketone.

Cited by 5 publications

References 87 publications

Pharmacophore‐based, rationale design, and efficient synthesis of novel tetrahydrobenzo[b]thiophene candidates as potential dual Topo I/II inhibitors and DNA intercalators

Pharmacophore‐based, rationale design, and efficient synthesis of novel tetrahydrobenzo[b]thiophene candidates as potential dual Topo I/II inhibitors and DNA intercalators

Synthesis and evaluation of larvicidal efficacy against C. pipiens of some new heterocyclic compounds emanated from 2‐cyano‐N′‐(2‐(2,4‐dichlorophenoxy)acetyl)acetohydrazide

Efficient synthesis and molecular docking analysis of quinazoline and azole hybrid derivatives as promising agents for anti-cancer and anti-tuberculosis activities

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