Inhibition of cartilage breakdown by isothiazolones

Wright, Stephen W.; Petraitis, Joseph J.; Abelman, Matthew M.; Bostrom, Lori L.; Corbett, Ronald L.; Green, Alicia M.; Kindt, Rachel M.; Sherk, Susan R.; Magolda, Ronald L.

doi:10.1016/s0960-894x(01)80782-4

Cited by 8 publications

(2 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,2-Benzisothiazol-3(2 H )-one (BIT) derivatives are an important class of heterocyclic compounds with a broad range of applications in the field of medicinal chemistry [ 22 , 23 , 24 , 25 ]. BIT derivatives ( Figure 1 ) have shown a wide range of biological activities, such as anticancer [ 26 ], antimicrobial [ 27 ], antifungal [ 28 ] and antiviral activities [ 14 , 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis and In Vitro Activity of N-Substituted 1,2-Benzisothiazol-3(2H)-ones against Dengue Virus NS2BNS3 Protease

et al. 2021

View full text Add to dashboard Cite

Several new N-substituted 1,2-benzisothiazol-3(2H)-ones (BITs) were synthesised through a facile synthetic route for testing their anti-dengue protease inhibition. Contrary to the conventional multistep synthesis, we achieved structurally diverse BITs with excellent yields using a two-step, one-pot reaction strategy. All the synthesised compounds were prescreened for drug-like properties using the online Swiss Absorption, Distribution, Metabolism and Elimination (SwissADME) model, indicating their favourable pharmaceutical properties. Thus, the synthesised BITs were tested for inhibitory activity against the recombinant dengue virus serotype-2 (DENV-2) NS2BNS3 protease. Dose–response experiments and computational docking analyses revealed that several BITs bind to the protease in the vicinity of the catalytic triad with IC50 values in the micromolar range. The DENV2 infection assay showed that two BITs, 2-(2-chlorophenyl)benzo[d]isothiazol-3(2H)-one and 2-(2,6-dichlorophenyl)benzo[d]isothiazol-3(2H)-one, could suppress DENV replication and virus infectivity. These results indicate the potential of BITs for developing new anti-dengue therapeutics.

show abstract

Section: Introductionmentioning

confidence: 99%

Facile Synthesis and In Vitro Activity of N-Substituted 1,2-Benzisothiazol-3(2H)-ones against Dengue Virus NS2BNS3 Protease

et al. 2021

View full text Add to dashboard Cite

show abstract

“…26-28 As an important class of heterocyclic compounds, 1,2-benzisothiazol-3(2H)-ones show broad spectrum bioactivity. 29-32 Among these, suitably-substituted 1,2-benzisothiazol-3(2H)-ones have been shown to exhibit potent antifungal 33 and antivirus activity. 17 Compounds containing a 1,3,4-oxadiazole template have also received significant attention in medicinal and pharmaceutical research as this structural motif has found use in a variety of applications, 34 including as an essential component of the pharmacophore and as a bioisosteric replacement for carbonyl-containing compounds, such as esters, amides and others.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and characterization of novel 1,2-benzisothiazol-3(2H)-one and 1,3,4-oxadiazole hybrid derivatives: Potent inhibitors of Dengue and West Nile virus NS2B/NS3 proteases

Lai

Dou

Aravapalli

et al. 2013

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

1,2-Benzisothiazol-3(2H)-ones and 1,3,4-oxadiazoles individually have recently attracted considerable interest in drug discovery, including as antibacterial and antifungal agents. In this study, a series of functionalized 1,2-benzisothiazol-3(2H)-one - 1,3,4-oxadiazole hybrid derivatives were synthesized and subsequently screened against Dengue and West Nile virus proteases. Ten out of twenty-four compounds showed greater than 50% inhibition against DENV2 and WNV proteases ([I] = 10 μM). The IC50 values of compound 7n against DENV2 and WNV NS2B/NS3 were found to be 3.75 ± 0.06 and 4.22 ± 0.07 μM, respectively. The kinetics data support a competitive mode of inhibition by compound 7n. Molecular modeling studies were performed to delineate the putative binding mode of this series of compounds. This study reveals that the hybrid series arising from the linking of the two scaffolds provides a suitable platform for conducting a hit-to-lead optimization campaign via iterative structure-activity relationship studies, in vitro screening and X-ray crystallography.

show abstract

Preparation of benzisothiazolones from 2-bromobenzamides and sulfur under copper catalysis conditions

Krasikova

Katkevičs

2013

Chem Heterocycl Comp

View full text Add to dashboard Cite

Inhibition of cartilage breakdown by isothiazolones

Cited by 8 publications

References 10 publications

Facile Synthesis and In Vitro Activity of N-Substituted 1,2-Benzisothiazol-3(2H)-ones against Dengue Virus NS2BNS3 Protease

Facile Synthesis and In Vitro Activity of N-Substituted 1,2-Benzisothiazol-3(2H)-ones against Dengue Virus NS2BNS3 Protease

Design, synthesis and characterization of novel 1,2-benzisothiazol-3(2H)-one and 1,3,4-oxadiazole hybrid derivatives: Potent inhibitors of Dengue and West Nile virus NS2B/NS3 proteases

Preparation of benzisothiazolones from 2-bromobenzamides and sulfur under copper catalysis conditions

Contact Info

Product

Resources

About