Novel Armed Pyrazolobenzothiazine Derivatives: Synthesis, X-Ray Crystal Structure and POM analyses of Biological Activity Against Drug Resistant Clinical Isolate of Staphylococcus aureus

Sajid, Zara; Ahmad, Matloob; Aslam, Sana; Ashfaq, Usman Ali; Zahoor, Ameer Fawad; Saddique, Furqan Ahmad; Parvez, Masood; Hameed, Abdul; Sultan, Sadia; Zgou, H.; Hadda, Taïbi Ben

doi:10.1007/s11094-016-1417-y

Cited by 19 publications

(5 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To access the pharmacokinetic profile of the tested compounds, we employed Petra/Osiris/Molinspiration (POM) analyses. The results of theoretical toxicity risks of compounds 1a-1f, which are calculated with the aid of the Petra/Osiris/Molinspiration (POM) program are shown in Table 3 [30][31][32]. Our findings reveal that all synthesized compounds 1a-1f, are not toxic and can be utilized as therapeutic agents.…”

Section: Pom Analyses Of Compounds (1a-1f)mentioning

confidence: 81%

DFT Study, POM Analyses and Molecular Docking of Novel Oxazaphosphinanes: Identification of Antifungal Pharmacophore Site

et al. 2020

Self Cite

View full text Add to dashboard Cite

A computational Petra/Osiris/Molinspiration/DFT(POM/DFT) based model has been developed for the identification of physico-chemical parameters governing the bioactivity of series of oxazaphosphinanes derivatives 1a-1f containing potential antifungal O,N-pharmacophore. A molecular docking study was performed in order to evaluate synthesized compounds, their possible antifungal properties, and their interactions in the binding site. Molecular docking studies revealed that the compounds 1a-1f have the potential to become lead molecules in the drug discovery process. The six compounds 1a-1f analyzed here were previously synthesized by our group.

show abstract

Section: Pom Analyses Of Compounds (1a-1f)mentioning

confidence: 81%

DFT Study, POM Analyses and Molecular Docking of Novel Oxazaphosphinanes: Identification of Antifungal Pharmacophore Site

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…Among the evaluated compounds, the derivatives 12a, 12c, 12g, 12i and 12k exhibited prominent inhibition of the yeast α-glucosidase enzyme [68,69] 5), which were less than the reference drug, acarbose (IC 50 = 58.8 µM [42,43]). Similarly, these derivatives were proven more effective α-glucosidase inhibitors in comparison to the reported benzimidazoles [70], dihydropyrano[2,3-c]pyrazoles [71] and 2-thioxobenzo[g]quinazolines [72] but less potent than the sulfonamide chalcones [44].…”

Section: α-Glucosidase Inhibitionmentioning

confidence: 95%

“…Furthermore, the 1,2-benzothiazine-3-carbohydrazides 6 and 7 (Figure 1) were proven good α-glucosidase inhibitors, with IC 50 values of 3.9 and 4.2 µM, respectively [29,30]. Some other biological activities shown by 1,2-benzothiazine derivatives are MAO inhibitors [31], α-glucosidase inhibitors [32,33], anti-inflammatory agents [34], antiviral agents [35][36][37][38], anticancer agents [39,40], antitumor agents [41], cholinesterase inhibitors [42] and anti-microbial agents [43]. In addition, various sulfonamides were also found to be good inhibitors of α-glucosidase [44] and α-amylase [45] enzymes.…”

Section: Introductionmentioning

confidence: 99%

Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

et al. 2022

Self Cite

View full text Add to dashboard Cite

Diabetes mellitus (DM), a complicated metabolic disorder, is due to insensitivity to insulin function or reduction in insulin secretion, which results in postprandial hyperglycemia. α-Glucosidase inhibitors (AGIs) and α-amylase inhibitors (AAIs) block the function of digestive enzymes, which delays the carbohydrate hydrolysis process and ultimately helps to control the postprandial hyperglycemia. Diversified 2-(3-(3-methoxybenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)-N-arylacetamides were synthesized and evaluated for their in vitro inhibitory potential against α-glucosidase and α-amylase enzymes. The compounds with chloro, bromo and methyl substituents demonstrated good inhibition of α-glucosidase enzymes having IC50 values in the range of 25.88–46.25 μM, which are less than the standard drug, acarbose (IC50 = 58.8 μM). Similarly, some derivatives having chloro, bromo and nitro substituents were observed potent inhibitors of α-amylase enzyme, with IC50 values of 7.52 to 15.06 μM, lower than acarbose (IC50 = 17.0 μM). In addition, the most potent compound, N-(4-bromophenyl)-2-(4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)acetamide (12i), was found to be a non-competitive and competitive inhibitor of α-glucosidase and α-amylase enzymes, respectively, during kinetic studies. The molecular docking studies provided the binding modes of active compounds and the molecular dynamics simulation studies of compound 12i in complex with α-amylase also showed that the compound is binding in a fashion similar to that predicted by molecular docking studies.

show abstract

“…POM physicochemical analysis or ADME/T is important to qualify drugs and their efficacy as leading candidates against various biotargets, as like antibacterial (Grib et al, 2020;Hatzade et al, 2015;Jamalis et al, 2020;Jarrahpour et al,2019;Mabkhot et al, 2015Mabkhot et al, , 2016Messali et al, 2014Messali et al, , 2015Nasruddin et al, 2018;Rad et al, 2017;Rbaa et al, 2019;Sajid et al, 2016;Tatar et al, 2016), antifungal (Al-Maqtari et al, 2017Khan et al, 2017;Rachedi et al, 2020;Radi et al, 2015;Tighadouni et al, 2016;Titi et al, 2019), antiviral (Chander et al, 2017;Lahsasni et al, 2015), antitumoral (Bechlem et al, 2020;Kamal et al, 2019;Piaz et al, 2018;Rachedi et al, 2019Rachedi et al, , 2020Youssoufi et al, 2015), antiparasitic drugs and various enzymes inhibitors (Amirkhanov et al, 2019;Ben Hadda et al, 2018Mabkhot et al, 2014;Rauf et al, 2017). The POM physicochemical calculations included a partition coefficient (cLogP), aqueous solubility, donor hydrogen bond, and drug-likeness, evaluated in terms of Lipinski's ruleof-five.…”

Section: Pom Analyses and Identification Of Pharmacophore Sitesmentioning

confidence: 99%

How to face COVID-19: proposed treatments based on remdesivir and hydroxychloroquine in the presence of zinc sulfate. Docking/DFT/POM structural analysis

Hadda

Berredjem

Almalki

et al. 2021

Journal of Biomolecular Structure and Dynamics

View full text Add to dashboard Cite

Remdesivir and hydroxychloroquine derivatives form two important classes of heterocyclic compounds. They are known for their anti-malarial biological activity. This research aims to analyze the physicochemical properties of remdesivir and hydroxychloroquine compounds by the computational approach. DFT, docking, and POM analyses also identify antiviral pharmacophore sites of both compounds. The antiviral activity of hydroxychloroquine compound's in the presence of zinc sulfate and azithromycin is evaluated through its capacity to coordinate transition metals (M = Cu, Ni, Zn, Co, Ru, Pt). The obtained bioinformatic results showed the potent antiviral/antibacterial activity of the prepared mixture (Hydroxychloroquine/Azithromycin/Zinc sulfate) for all the opportunistic Gram-positive, Gram-negative in the presence of coronavirus compared with the complexes Polypyridine-Ruthenium-di-aquo. The postulated zinc(II) complex of hydroxychloroquine derivatives are indeed an effective antibacterial and antiviral agent against coronavirus and should be extended to other pathogens. The combination of a pharmacophore site with a redox [Metal(OH 2 ) 2 ] moiety is of crucial role to fight against viruses and bacteria strains. Communicated by Ramaswamy H. Sarma

show abstract

Novel Armed Pyrazolobenzothiazine Derivatives: Synthesis, X-Ray Crystal Structure and POM analyses of Biological Activity Against Drug Resistant Clinical Isolate of Staphylococcus aureus

Cited by 19 publications

References 15 publications

DFT Study, POM Analyses and Molecular Docking of Novel Oxazaphosphinanes: Identification of Antifungal Pharmacophore Site

DFT Study, POM Analyses and Molecular Docking of Novel Oxazaphosphinanes: Identification of Antifungal Pharmacophore Site

Identification of Cyclic Sulfonamides with an N-Arylacetamide Group as α-Glucosidase and α-Amylase Inhibitors: Biological Evaluation and Molecular Modeling

How to face COVID-19: proposed treatments based on remdesivir and hydroxychloroquine in the presence of zinc sulfate. Docking/DFT/POM structural analysis

Contact Info

Product

Resources

About