2-(1H-Pyrazol-1-yl)acetic acids as chemoattractant receptor-homologous molecule expressed on Th2 lymphocytes (CRTh2) antagonists

Andrés, Míriam; Bravo, Mònica; Buil, Maria Antonia; Calbet, Marta; Castillo, Marcos; Castro, Jordi; Eichhorn, Peter; Ferrer, Manel; Lehner, Martin D.; Moreno, Imma; Roberts, Richard S.; Sevilla, Sara

doi:10.1016/j.ejmech.2013.10.072

Cited by 12 publications

(3 citation statements)

References 30 publications

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“…Incidentally, compound 28 has been disclosed as a compound developed by Pettipher et al from Oxagen [ 88 ]. The K i of the compound was reportedly 5 nM [ 89 ].…”

Section: Indole-based Potential Gpr44 Analoguesmentioning

confidence: 99%

Indole-Based and Cyclopentenylindole-Based Analogues Containing Fluorine Group as Potential 18F-Labeled Positron Emission Tomography (PET) G-Protein Coupled Receptor 44 (GPR44) Tracers

Yin,

Huang,

Huang

et al. 2023

Pharmaceuticals

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Recently, growing evidence of the relationship between G-protein coupled receptor 44 (GPR44) and the inflammation-cancer system has garnered tremendous interest, while the exact role of GPR44 has not been fully elucidated. Currently, there is a strong and urgent need for the development of non-invasive in vivo GPR44 positron emission tomography (PET) radiotracers that can be used to aid the exploration of the relationship between inflammation and tumor biologic behavior. Accordingly, the choosing and radiolabeling of existing GPR44 antagonists containing a fluorine group could serve as a viable method to accelerate PET tracers development for in vivo imaging to this purpose. The present study aims to evaluate published (2000-present) indole-based and cyclopentenyl-indole-based analogues of the GPR44 antagonist to guide the development of fluorine-18 labeled PET tracers that can accurately detect inflammatory processes. The selected analogues contained a crucial fluorine nuclide and were characterized for various properties including binding affinity, selectivity, and pharmacokinetic and metabolic profile. Overall, 26 compounds with favorable to strong binding properties were identified. This review highlights the potential of GPR44 analogues for the development of PET tracers to study inflammation and cancer development and ultimately guide the development of targeted clinical therapies.

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“…Incidentally, compound 28 has been disclosed as a compound developed by Pettipher et al from Oxagen [ 88 ]. The K i of the compound was reportedly 5 nM [ 89 ].…”

Section: Indole-based Potential Gpr44 Analoguesmentioning

confidence: 99%

Indole-Based and Cyclopentenylindole-Based Analogues Containing Fluorine Group as Potential 18F-Labeled Positron Emission Tomography (PET) G-Protein Coupled Receptor 44 (GPR44) Tracers

Yin,

Huang,

Huang

et al. 2023

Pharmaceuticals

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“…An acidic deprotection [23] was favored over the previously used hydrogenolysis reaction [16] due to the faster reaction time (30 min) and easier work-up. Finally, oxidation of sulfide 2g to sulfone 2h was achieved by treatment with m-CPBA in a moderate yield (46%) [24].…”

Section: Chemistrymentioning

confidence: 99%

Enhancing activity and selectivity in a series of pyrrol-1-yl-1-hydroxypyrazole-based aldose reductase inhibitors: The case of trifluoroacetylation

Papastavrou

Chatzopoulou

Ballekova

et al. 2017

European Journal of Medicinal Chemistry

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“…Because of the particularity of the structures, this kind of compounds have a good coordination performance which we can find in Chen and Su's works [1][2][3][4][5], and their fluorescence activity [6], adsorptive property [7] have been reported before. Recently, this kind of compounds are widely researched in the field of molecular biology, such as ubiquitin agent inhibitors [8], 11-beta-hydroxysteroid dehydrogenase type I inhibitor [9]，JAMM proteins inhibitor [10] ， potential 5-HT 6 receptor [11] ， CRTh 2 antagonists [12] ， Keap1-Nrf2…”

mentioning

confidence: 99%

Crystal structures and biological activities of a symmetrical quinoline thioether ligand and its transition metal complexes

Zou

Zhang

et al. 2015

Inorganic Chemistry Communications

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Pan, Crystal structures and biological activities of a symmetrical quinoline thioether ligand and its transition metal complexes, Inorganic Chemistry Communications (2015), Abstract: The ligand 2, 6-bis (8-quinolinylthiomethyl) pyridine and its four transition metal complexes have been synthesized and characterized by elemental analysis (EA), infrared spectra (IR) and single-crystal diffraction. It was revealed that compounds 1-3 were comprised of discrete mononuclear units and double nuclear structure in compound 4. The antibacterial activities and pesticide activities of the ligand and the complexes 1-4 were tested. The results showed some compounds had absolute specificity for certain bacteria, and could have good application prospect in pharmaceutical and agricultural use.Chemical structure of the compounds containing quinoline thioether group has been the focus of attention. Because of the particularity of the structures, this kind of compounds have a good coordination performance which we can find in Chen and Su's works [1-5], and their fluorescence activity [6], adsorptive property [7] have been reported before. Recently, this kind of compounds are widely researched in the field of molecular biology, such as ubiquitin agent inhibitors [8], 11-beta-hydroxysteroid dehydrogenase type I inhibitor [9]，JAMM proteins inhibitor [10] ， potential 5-HT 6 receptor [11] ， CRTh 2 antagonists [12] ， Keap1-Nrf2 Small-Molecule Inhibitors [13], et al. However, reports on the bioactivities of such kinds of complexes still remain rare. The asymmetric thioether ligand, prepared by Akerkar A. S. in 1970s,has been proven to be an excellent antitubercular agent [14]. In order to probe the potential drug activity of such kind of compounds, the pyridine terminal group was taken as a carrier, which might be a synergisitic activity group we have probed before [15][16][17][18], and reacted with 2 times of equivalent of quinoline thiol groups, the symmetry of quinoline sulfur ether ligand 2, 6-bis (8-quinolinylthiomethyl) pyridine (L) was synthesized. The complexes of [Cu(L)(CF 3 SO 3 )]·(CF 3 SO 3 ) (1), [Cd(L)](ClO 4 ) 2 (H 2 O) 2 (2), [Zn(L)(CO 2 CF 3 )]·(ClO 4 )·CH 3 CN (3), and [Co(L)CoCl 4 ]·CH 3 OH (4) were obtained by coordinating with a series of transition metal salts. All the compounds were characterized by elemental analysis (EA), infrared spectra (IR) and single-crystal diffraction, their antibacterial and pesticides activities were tested. Single-crystal X-ray diffraction measurements of the ligand and complexes 1-4 were carried out on an Oxford Gemini S Ultra CCD diffractometer equipped with a graphite monochromator at 150 K. The determination of unit cell parameters and data collections were performed with Mo-K α radiation (λ = 0.71073 Å). The unit cell parameters were obtained with least-squares refinements and all structures were solved by direct methods [19]. The metal atoms in each complex were located from E-maps. The other non-hydrogen atoms were located in successive difference Fourier syntheses. The final refine...

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2-(1H-Pyrazol-1-yl)acetic acids as chemoattractant receptor-homologous molecule expressed on Th2 lymphocytes (CRTh2) antagonists

Cited by 12 publications

References 30 publications

Indole-Based and Cyclopentenylindole-Based Analogues Containing Fluorine Group as Potential 18F-Labeled Positron Emission Tomography (PET) G-Protein Coupled Receptor 44 (GPR44) Tracers

Indole-Based and Cyclopentenylindole-Based Analogues Containing Fluorine Group as Potential 18F-Labeled Positron Emission Tomography (PET) G-Protein Coupled Receptor 44 (GPR44) Tracers

Enhancing activity and selectivity in a series of pyrrol-1-yl-1-hydroxypyrazole-based aldose reductase inhibitors: The case of trifluoroacetylation

Crystal structures and biological activities of a symmetrical quinoline thioether ligand and its transition metal complexes

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