Synthesis, monoamine oxidase inhibition activity and molecular docking studies of novel 4-hydroxy-N′-[benzylidene or 1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides

Saddique, Furqan Ahmad; Zaib, Sumera; Jalil, Saquib; Aslam, Sana; Ahmad, Matloob; Sultan, Sadia; Naz, Humera; Iqbal, Mazhar; Iqbal, Jamshed

doi:10.1016/j.ejmech.2017.10.036

Cited by 32 publications

(22 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The best docking conformation having minimum final docking energy or free energy (ΔG) was used for further calculations throughout. Binding propensity of drugs with DNA in terms of binding constants ( K b ) was calculated from the lowest ΔG values [ 38 , 39 , 40 ]. Remaining parameters were set default.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical, spectroscopic and theoretical monitoring of anthracyclines’ interactions with DNA and ascorbic acid by adopting two routes: Cancer cell line studies

et al. 2018

View full text Add to dashboard Cite

Pharmacodynamic interactions of three anthracycline antibiotics namely doxorubicin (DXH), epirubicin (EpiDXH) and daunorubicin (DNR) with DNA in the absence and presence of ascorbic acid (AA) as natural additive were monitored under physiological conditions (pH = 7.4, 4.7 and T = 309.5K). Route–1 (Anthracycline–AA–DNA) and Route–2 (Anthracycline–DNA–AA) were adopted to see the interactional behavior by cyclic voltammetry (CV) and UV-visible spectroscopy. In comparison to Route–2; voltammetric and spectral responses as well as binding constant (Kb) and Gibb’s free energy change (ΔG) values revealed strongest and more favorable interaction of anthracycline–AA complex with DNA via Route–1. Kb, s (binding site sizes) and ΔG evaluated from experimental (CV, UV-Vis) and theoretical (molecular docking) findings showed enhanced binding strength of tertiary complexes as compared to binary drug–DNA complexes. The results were found comparatively better at pH 7.4. Consistency was observed in binding parameters evaluated from experimental and theoretical techniques. Diffusion coefficients (Do) and heterogeneous electron transfer rate constant (ks,h) confirmed the formation of complexes via slow diffusion kinetics. Percent cell inhibition (%Cinh) of anthracyclines for non-small cell cancer cell lines (NSCCLs) H-1299 and H-157 were evaluated higher in the presence of AA which further complimented experimental and theoretical results.

show abstract

Section: Methodsmentioning

confidence: 99%

Electrochemical, spectroscopic and theoretical monitoring of anthracyclines’ interactions with DNA and ascorbic acid by adopting two routes: Cancer cell line studies

et al. 2018

View full text Add to dashboard Cite

show abstract

“…). In silico studies like molecular docking , ADME‐Tox , pharmacophore , and molecular dynamics have suggested potent hypothetical prediction of the new molecule.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological andIn SilicoStudy of Fluorine‐Containing Quinoline Hybrid Thiosemicarbazide Analogues

Patel

Prajapati

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A novel series of fluorine‐containing quinoline hybrid thiosemicarbazide analogues (8a–8l) were synthesized and tested for their biological activities. The antibacterial results demonstrated that compounds 8d and 8l [minimal inhibitory concentration (MIC) 62.5 μg/mL] were shown to have higher biological activity than ampicillin against Escherichia coli. Compound 8b (MIC 25 μg/mL) was shown to have the highest activity than was ampicillin against Staphylococcus aureus. The antifungal results demonstrated that compound 8j (MIC 100 μg/mL) has shown good activity. Most of the targeted compounds have shown potent antimalarial activity. Compounds 8d (0.19 μg/mL), 8g (0.30 μg/mL), 8h (0.36 μg/mL), 8k (0.10 μg/mL), 8l (0.28 μg/mL), 8k (0.10 μg/mL), and 8l (0.28 μg/mL) have notable activity than does the reference drug quinine. Compounds 8d (0.27 μg/mL), 8g (0.30 μg/mL), and 8k (0.17 μg/mL) have shown excellent activity against chloroquine‐resistant strain. The MTT assay performed on peripheral blood lymphocyte cultures showed a high percentage of lymphocyte viability [8d (99.64), 8g (99.46), 8h (98.83), and 8k (99.51)] at a maximum dose (10 μg/mL), depicting no cytotoxicity of these compounds on human lymphocytes in vitro. A molecular docking study was performed on Pf‐DHFR‐TS inhibitor. A molecular dynamics study has shown compound 8g to have better affinity with protein. ADME‐Tox and pharmacophore study of synthesized compounds suggested prediction of active site.

show abstract

“… [33] The precursor 1,2‐benzothiazine ( 3 ) was prepared by coupling sodium saccharine with methyl chloroacetate with subsequent ring expansion of the product by Gabriel‐Colemann rearrangement reaction. Benzimidazole‐benzothiazine hybrid ( 4 ) was obtained by condensation of benzothiazine ( 3 ) [40] with 2‐chloromethylbenzimidazole. The formation of the hybridized product was confirmed by the appearance of N −CH 2 peak at 4.8‐4.9 ppm in the 1 H NMR spectrum and by the appearance of M + ion peak in mass spectrometry.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Nucleotide Pyrophosphatase/Phosphodiesterase Inhibition Studies of Carbohydrazides Based on Benzimidazole‐Benzothiazine Skeleton

et al. 2020

Self Cite

View full text Add to dashboard Cite

Ecto‐nucleotide pyrophosphatases/phosphodiesterases (ENPPs) are important family of ecto‐nucleotidases. There are seven members of ENPP family out of which ENPP1 and ENPP3 hydrolyze nucleotides whereas, ENPP2 preferably hydrolyzes phospholipids as compared to nucleotides. Overexpression of ENPP1 and ENPP3 has been reported to be associated with many health disorders such as diabetes, chondrocalcinosis, osteoarthritis, and cancer. Development of ENPP1 and −3 inhibitors might be useful for the treatment of these disorders. This study aimed to investigate the inhibitory potentials of the synthesized benzimidazole‐benzothiazine hybrid molecules on ecto‐nucleotide pyrophosphatases/phosphodiesterases (ENPPs) enzymes. A series of benzimidazole‐benzothiazine hybrid molecules was synthesized by Gabriel–Colman rearrangement of methyl 2‐(1,1‐dioxido‐3‐oxobenzo[d]isothiazol‐2(3H)‐yl)acetate. The successfully synthesized compounds (6 a–6 m) were evaluated for ENPP1 and −3 inhibitory activities. Among the investigated compounds 6 m with an IC50 value of 0.14 μM, and 6 h with an IC50 value of 0.12 μM, were found to be the most potent inhibitors of ENPP1 and −3, respectively. Molecular docking studies of most active and selective inhibitors showed putative mode of binding interactions responsible for highest potency and selectivity of docked inhibitors. The overall in‐silico results were found to be highly correlated with in‐vitro results showed in Table 1.

show abstract

Synthesis, monoamine oxidase inhibition activity and molecular docking studies of novel 4-hydroxy-N′-[benzylidene or 1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides

Cited by 32 publications

References 53 publications

Electrochemical, spectroscopic and theoretical monitoring of anthracyclines’ interactions with DNA and ascorbic acid by adopting two routes: Cancer cell line studies

Electrochemical, spectroscopic and theoretical monitoring of anthracyclines’ interactions with DNA and ascorbic acid by adopting two routes: Cancer cell line studies

Design, Synthesis, and Biological andIn SilicoStudy of Fluorine‐Containing Quinoline Hybrid Thiosemicarbazide Analogues

Synthesis and Nucleotide Pyrophosphatase/Phosphodiesterase Inhibition Studies of Carbohydrazides Based on Benzimidazole‐Benzothiazine Skeleton

Contact Info

Product

Resources

About