Design, synthesis and docking studies of new furobenzopyranones and pyranobenzopyranones as photoreagent towards DNA and as antimicrobial agents

Farag, Nahla A.; Eltayeb, Wafaa N

doi:10.1016/j.ejmech.2009.10.016

Cited by 19 publications

(8 citation statements)

References 41 publications

(48 reference statements)

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“…Ar-H),9.77, 10.07,10.54 (3s, 3H, 3NH),11.45 (s, 1H, OH) 13. C-NMR (90 MHz): 14.33, 115.38, 117.65, 119.38, 121.26, 124.88, 125.95, 126.89, 127.27, 128.50, 129.82, 132.49, 157.82, 168.21, 188.14.…”

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confidence: 99%

“…For many years, designing novel members of this group was based only on the available data on the structure–activity relationships. However, in the recent years, researchers have focused on determining the molecular mechanism of action of thiosemicarbazides . The results of both biological tests and in silico analyses have indicated the inhibition of bacterial topoisomerase IV as one of those mechanisms .…”

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confidence: 99%

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Structure–activity Relationship Studies of Microbiologically Active Thiosemicarbazides Derived from Hydroxybenzoic Acid Hydrazides

et al. 2014

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Forty-five derivatives of thiosemicarbazide were synthesized, and their antibacterial activity against Gram-positive and Gram-negative bacteria was evaluated. Some of the described compounds exhibited interesting activity against reference strains of Gram-positive bacteria, whereas only two derivatives had the ability to inhibit the growth of Gram-negative species (Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 13883, Proteus mirabilis ATCC 12453). The most potent antimicrobial activity was observed in the cases of salicylic acid hydrazide derivatives. The differences in activity inspired us to conduct conformational analysis using molecular mechanics level. The obtained results suggest that the molecule geometry, especially at the N4-terminus of thiosemicarbazide skeleton, determines the antibacterial activity. Unfortunately, in opposition to what we expected, only one of the tested compounds inhibited the activity of the topoIV enzyme, and none of them was active against DNA gyrase.

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Structure–activity Relationship Studies of Microbiologically Active Thiosemicarbazides Derived from Hydroxybenzoic Acid Hydrazides

et al. 2014

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“…The chemical formulae of synthetic compounds used in this study are shown in Table 1. They were synthesized according to [19]. Compound 10 is newly synthesized following the equation shown in Figure 1.…”

Section: Chemical Compoundsmentioning

confidence: 99%

Delineate the role of plant fuorocoumarin derivatives on hepatocarcinoma, DNA Topoisomerase I and mitotic cell division

Esmat¹,

Farag²,

Barakat³

et al. 2017

Cancer Rep Rev

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Furocoumarins are produced by plant members via the phenylpropanoid pathway. Natural and chemically synthesized furocoumarins exhibit promising anticancer activity. This work aims to increase our understanding of the mechanism by which these compounds can suppress cancer. Therefore, two medicinal plants, Apium graveolense & Ruta graveolense and 10 synthesized furocoumarin derivative compounds were tested against hepatocellular carcinoma cell line (HepG-2). Our results indicated that compound 9 exhibited the highest cytotoxic activity (IC 50 =11.9 µM). Other compounds exerted less cytotoxic activity ranging from IC 50 =28.38 µM for compound one to IC 50 =67.10 µM in case of compound 5. The natural crude extracts exhibited the lowest cytotoxic activity on HepG-2 with values of IC 50 =312.4 and 445.7 µM for Ruta graveolens and Apium graveolens, respectively. Compound 9 was found to inhibit topoisomerase I enzyme, based on the molecular docking analysis, and significantly suppressed the mitotic cell division in the meristematic cells of pea (Pisum sativum) root tips.

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“…that have developed remarkable resistance to available fungal drugs and are threatening human health and life [ 6 ]. Accordingly, the scientific community is striving in a race against time to innovate new antimicrobial drugs from plants [ 7 ], nanoparticles [ 8 ] and synthesized compounds [ 9 ]. In this context, synthesizing new molecules and evaluating their antimicrobial activity constitute essential approaches to discovering new potential antimicrobial and antiviral agents [ 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, In Silico and POM Studies for the Identification of the Pharmacophore Sites of Benzylidene Derivatives

et al. 2023

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Due to the uneven distribution of glycosidase enzyme expression across bacteria and fungi, glycoside derivatives of antimicrobial compounds provide prospective and promising antimicrobial materials. Therefore, herein, we report the synthesis and characterization of six novel methyl 4,6-O-benzylidene-α-d-glucopyranoside (MBG) derivatives (2–7). The structures were ascertained using spectroscopic techniques and elemental analyses. Antimicrobial tests (zone of inhibition, MIC and MBC) were carried out to determine their ability to inhibit the growth of different Gram-positive, Gram-negative bacteria and fungi. The highest antibacterial activity was recorded with compounds 4, 5, 6 and 7. The compounds with the most significant antifungal efficacy were 4, 5, 6 and 7. Based on the prediction of activity spectra for substances (PASS), compounds 4 and 7 have promising antimicrobial capacity. Molecular docking studies focused on fungal and bacterial proteins where derivatives 3 and 6 exhibited strong binding affinities. The molecular dynamics study revealed that the complexes formed by these derivatives with the proteins L,D-transpeptidase Ykud and endoglucanase from Aspergillus niger remained stable, both over time and in physiological conditions. Structure–activity relationships, including in vitro and in silico results, revealed that the acyl chains [lauroyl-(CH3(CH2)10CO-), cinnamoyl-(C6H5CH=CHCO-)], in combination with sugar, were found to have the most potential against human and fungal pathogens. Synthetic, antimicrobial and pharmacokinetic studies revealed that MBG derivatives have good potential for antimicrobial activity, developing a therapeutic target for bacteria and fungi. Furthermore, the Petra/Osiris/Molinspiration (POM) study clearly indicated the presence of an important (O1δ−----O2δ−) antifungal pharmacophore site. This site can also be explored as a potential antiviral moiety.

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Design, synthesis and docking studies of new furobenzopyranones and pyranobenzopyranones as photoreagent towards DNA and as antimicrobial agents

Cited by 19 publications

References 41 publications

Structure–activity Relationship Studies of Microbiologically Active Thiosemicarbazides Derived from Hydroxybenzoic Acid Hydrazides

Structure–activity Relationship Studies of Microbiologically Active Thiosemicarbazides Derived from Hydroxybenzoic Acid Hydrazides

Delineate the role of plant fuorocoumarin derivatives on hepatocarcinoma, DNA Topoisomerase I and mitotic cell division

Design, Synthesis, In Silico and POM Studies for the Identification of the Pharmacophore Sites of Benzylidene Derivatives

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