Synthesis and Biological Activity of a Series of Novel <i>N</i>‐Substituted β‐Lactams Derived from Natural Gallic Acid

Cancer is the second most common cause of death in the USA. Among the known classes of anticancer agents, the microtubule-targeted antimitotic drugs are considered to be one of the most important. They are usually classified into microtubule-destabilizing (e.g., Vinca alkaloids) and microtubule-stabilizing (e.g., paclitaxel) agents. Combretastatin A4 (CA-4), which is a natural stilbene isolated from Combretum caffrum, is a microtubule-destabilizing agent that binds to the colchicine domain on β-tubulin and exhibits a lower toxicity profile than paclitaxel or the Vinca alkaloids. In this paper, we describe the docking study, synthesis, antiproliferative activity and selectivity index of the N-acylhydrazone derivatives (5a–r) designed as CA-4 analogues. The essential structural requirements for molecular recognition by the colchicine binding site of β-tubulin were recognized, and several compounds with moderate to high antiproliferative potency (IC50 values ≤18 µM and ≥4 nM) were identified. Among these active compounds, LASSBio-1586 (5b) emerged as a simple antitumor drug candidate, which is capable of inhibiting microtubule polymerization and possesses a broad in vitro and in vivo antiproliferative profile, as well as a better selectivity index than the prototype CA-4, indicating improved selective cytotoxicity toward cancer cells.

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“…166–168°C. The melting point, 1 H NMR, 13 C NMR and IR data are in agreement with previous reports [29] . I.R.…”

Section: Methodssupporting

confidence: 92%

Docking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues

et al. 2014

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“…Regarding the phenolic acids, gallic acid, p -coumaric acid and chlorogenic acid were detected and quantified in all the bulb extracts analyzed, except L. lancifolium and L. pumilum , in which chlorogenic acid were not detected. Natural phenolic acids are strong antioxidants and exhibit potential antifungal, antibacterial, anti-inflammatory and anti-cancer activity [ 38 , 39 , 40 ]. p -Coumaric acid was the most predominant phenolic compound in the tested phenolic acids, ranging from 0.80 to 4.51 mg/100 g dw.…”

Section: Resultsmentioning

confidence: 99%

Phenolic Compounds and Antioxidant Activity of Bulb Extracts of Six Lilium Species Native to China

et al. 2012

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Lily (Lilium) is used as an important edible and medical plant species with a vague taxonomic classification and a long history in China. Bulbs of six Lilium species (L. regale, L. concolor, L. pumilum, L. leucanthum, L. davidii var. unicolor and L. lancifolium) native to China were investigated with a view to their exploitation as a potential source of natural antioxidants due to their phenolic composition and dietary antioxidant potential. The results showed that all bulb extracts exhibited strong antioxidant activities, which generally correlated positively with the total phenolic contents (r = 0.68 to 0.94), total flavonoid contents (r = 0.51 to 0.89) and total flavanol contents (r = 0.54 to 0.95). High-performance liquid chromatography (HPLC) analysis revealed that rutin and kaempferol were the major phenolic components in the extracts. Hierarchical cluster analysis showed that L. regale belonged to the group with high phenolic content and strong antioxidant power. L. concolor and L. pumilum were arranged in one group characterized by moderate phenolic content and antioxidant capacity, while L. leucanthum, L. davidii var. unicolor and L. lancifolium were clustered in the third group with low phenolic content and weak antioxidant activity. These strongly suggest that lily bulbs may serve as a potential source of natural antioxidant for food and pharmaceutical applications.

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“…Benzohydrazide derivatives (5)(6)(17)(18)(19) were synthesized by the reaction of esters (1-2, 11-13) with hydrazine hydrate in ethanol. The target compounds (7-10, 20-25) were synthesized by the reaction of benzohydrazide derivatives (5-6, 17-19) with various aromatic aldehyde in ethanol under reflux conditions [27,28]. The FT-IR, 1 H NMR, 13 C NMR and mass spectral analysis confirmed the structures of (7-10, 20-25).…”

Section: Chemistrymentioning

confidence: 87%

Synthesis, Biological Activity, and Molecular Docking Studied of New Substituted Hydrazones

Nabel B. Ayrim,

Asim A. Balakit,

Souad J. Lafta

2023

J. K. Chem. Sci.

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Series of new hydrazones derived from different carboxylic acid hydrazides and aromatic aldehydes (7-10, 20-25) have been synthesized and characterized by spectral techniques (FT-IR, 1H NMR, 13C NMR, and Mass spectrometry). The target compounds are designed to have the different substituents at the para position for both parts of the structures (hydrazide and aldehyde parts. The synthesized compounds have been evaluated as antimicrobial agents by studying their biological activity against two bacteria strains Staphylococcus aureus and Staphylococcus epidermidis (as gram-positive bacteria), Escherichia coli and Klebsiella sp (as gram-negative bacteria), the antifungal activity was studied against Candida albicans fungi. The obtained results showed a moderate antimicrobial activity for the test compounds when compared with ampicillin. The synthesized compounds were also subjected to molecular docking studies which were carried out against the bacteria strain Staphylococcus aureus DHFR.

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Synthesis and Biological Activity of a Series of Novel N‐Substituted β‐Lactams Derived from Natural Gallic Acid

Cited by 12 publications

References 39 publications

Docking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues

Docking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues

Phenolic Compounds and Antioxidant Activity of Bulb Extracts of Six Lilium Species Native to China

Synthesis, Biological Activity, and Molecular Docking Studied of New Substituted Hydrazones

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