Identification of Bidentate Salicylic Acid Inhibitors of PTP1B

Haftchenary, Sina; Jouk, Andriana O.; Aubry, Isabelle; Am, Lewis; Landry, Melissa; Ball, Daniel P.; Shouksmith, Andrew E.; Collins, Catherine V.; Tremblay, Michel L.; Gunning, Patrick T.

doi:10.1021/acsmedchemlett.5b00171

Cited by 17 publications

(8 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…92,93 They generated several inhibitors, the best of which ( 27) inhibited PTP1B with an IC 50 of 1.7 μM; however, despite using multiple salicylates to target both pTyr-binding pockets, these compounds were not selective for PTP1B over TC-PTP. 93 Glioblastoma multiforme (GBM) is an aggressive brain malignancy which is often characterized by constitutive STAT3 activation. Thus, GBM represents an important possible therapeutic indication for STAT3 inhibitors.…”

Section: Salicylates and Related Compoundsmentioning

confidence: 99%

Phosphotyrosine isosteres: past, present and future

Cerulli¹,

Kritzer

2020

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Section: Salicylates and Related Compoundsmentioning

confidence: 99%

Phosphotyrosine isosteres: past, present and future

Cerulli¹,

Kritzer

2020

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…Monomeric thioureas I–III and squaramides sq- I –sq- III were prepared (Scheme ), in two steps from 1 , easily obtained by reaction of commercially available 4-amino-2,6-dichlorophenol with 4-vinylbenzyl chloride and t -BuOK in DMF at 0 °C …”

Section: Resultsmentioning

confidence: 99%

Chiral Bifunctional Thioureas and Squaramides and Their Copolymers as Recoverable Organocatalysts. Stereoselective Synthesis of 2-Substituted 4-Amino-3-nitrobenzopyrans and 3-Functionalized 3,4-Diamino-4H-Chromenes

et al. 2018

View full text Add to dashboard Cite

Novel styryl-substituted thioureas and squaramides were obtained in three steps from commercially available 4-hydroxy-3,5-dichloroaniline. These organocatalysts promote cascade reactions in high yields and excellent stereoselection. By using only a 5 mol % loading of catalyst, it is possible to obtain 2,3,4-trisubstituted benzopyrans by reaction of α-amido sulfones derived from salicyladehydes and nitrostyrenes or 2,3,4-trisubstituted 4 H-chromenes by reaction of the same α-amido sulfones with (phenylsulfonyl)acetonitrile in excellent diastereo- and enantioselectivities. Two polymeric thioureas and squaramides were prepared by copolymerization of the best monomeric catalysts with styrene and divinylbenzene and used for the same transformations. These polymers behave also as excellent stereoselective catalysts that can be recovered and reused for five cycles.

show abstract

“…Interestingly, we found that some molecules having 1,2,3-triazoles ( 4 – 6 , Fig. 1 ) (Rao et al 2014 ; Haftchenary et al 2015 ; Shafi et al 2012 ) also showed good anti-inflammatory properties. Considering the individual biological activities, medicinal importance of ibuprofen and 1,4-disubstituted 1,2,3-triazoles, we designed novel class of small molecules ( 7 , Fig.…”

Section: Introductionmentioning

confidence: 94%

Synthesis, anti-inflammatory, bactericidal activities and docking studies of novel 1,2,3-triazoles derived from ibuprofen using click chemistry

et al. 2016

View full text Add to dashboard Cite

BackgroundNonsteroidal anti-inflammatory drugs are of vast therapeutic benefit in the treatment of different types of inflammatory conditions. 1,2,3-Triazoles and their derivatives have a wide range of applications as anti-bacterial, anti-fungal, anti-tubercular, cytostatic, anti-HIV, anti-allergic, anti-neoplastic and anti-inflammatory (AI) agents. Considering the individual biological and medicinal importance of ibuprofen and 1,2,3-triazoles, we wanted to explore novel chemical entities based on ibuprofen and triazole moieties towards their biological significance.ResultsClick chemistry has utilized as an ideal strategy to prepare novel ibuprofen-based 1,4-disubstituted 1,2,3-triazole containing molecules. These compounds were screened for their in vivo AI activity, among all the synthesized analogues 13o was shown potent effect than the reference AI drug ibuprofen at the same concentration (10 mg/kg body weight). Compounds 13l, 13g, 13c, 13k, 13i, 13n, 13m and 13j were shown significant AI activity. These triazole analogues were also screened for their bactericidal profile. Compounds 13c, 13i, 13l and 13o exhibited considerable bactericidal activity against gram positive and gram negative strains. In addition to this, molecular docking studies were also carried out into cyclooxygenase-2 active site to predict the affinity and orientation of these novel compounds (13a–q).ConclusionsIn summary, we have designed and synthesized 1,2,3-triazole analogues of ibuprofen in good yields using Click chemistry approach. AI and bactericidal activities of these compounds were evaluated and shown remarkable results.Electronic supplementary materialThe online version of this article (doi:10.1186/s40064-016-2052-5) contains supplementary material, which is available to authorized users.

show abstract

Identification of Bidentate Salicylic Acid Inhibitors of PTP1B

Cited by 17 publications

References 37 publications

Phosphotyrosine isosteres: past, present and future

Phosphotyrosine isosteres: past, present and future

Chiral Bifunctional Thioureas and Squaramides and Their Copolymers as Recoverable Organocatalysts. Stereoselective Synthesis of 2-Substituted 4-Amino-3-nitrobenzopyrans and 3-Functionalized 3,4-Diamino-4H-Chromenes

Synthesis, anti-inflammatory, bactericidal activities and docking studies of novel 1,2,3-triazoles derived from ibuprofen using click chemistry

Contact Info

Product

Resources

About