2133-40-6Relevant articles and documents
Conjugates of 1′-aminoferrocene-1-carboxylic acid and proline: Synthesis, conformational analysis and biological evaluation
Kovacevic, Monika,Molcanov, Kresimir,Radosevic, Kristina,Srcek, Visnja Gaurina,Roca, Suncica,Cace, Alan,Barisic, Lidija
, p. 12852 - 12880 (2014)
Our previous studies showed that alteration of dipeptides Y-Fca-Ala-OMe (III) into Y-Ala-Fca-OMe (IV) (Y = Ac, Boc; Fca = 1′-aminoferrocene-1- carboxylic acid) significantly influenced their conformational space. The novel bioconjugates Y-Fca-Pro-OMe (1, Y = Ac; 2, Y = Boc) and Y-Pro-Fca-OMe (3, Y = Boc; 4, Y = Ac) have been prepared in order to investigate the influence of proline, a well-known turn-inducer, on the conformational properties of small organometallic peptides with an exchanged constituent amino acid sequences. For this purpose, peptides 1-4 were subjected to detailed spectroscopic analysis (IR, NMR, CD spectroscopy) in solution. The conformation of peptide 3 in the solid state was determined. Furthermore, the ability of the prepared conjugates to inhibit the growth of estrogen receptor-responsive MCF-7 mammary carcinoma cells and HeLa cervical carcinoma cells was tested.
A dansyl-appended N-heterocycle for Cu2+ and S2? recognition via a displacement mode
Wang, Xu,Xia, Peng,Huang, Xiaohuan
, p. 98 - 104 (2019)
A novel L-proline based heterocycle 3 of C2 symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu2+ ion, and their interaction induces a remarkable fluorescence quenching in DMSO:H2O = 9:1 (HEPES buffer, 0.01 M, pH 7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu2+ complex exhibit specific fluorescence recovery upon addition of S2?, even in the presence of S2O3 2?, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of 1H NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential “on-off-on” fluorescence bio-imaging of the heterocycle 3 to Cu2+ and S2? was carried out in HeLa cells.
Captopril analogues as metallo-β-lactamase inhibitors
Yusof, Yusralina,Tan, Daniel T.C.,Arjomandi, Omid Khalili,Schenk, Gerhard,McGeary, Ross P.
, p. 1589 - 1593 (2016)
A number of captopril analogues were synthesised and tested as inhibitors of the metallo-β-lactamase IMP-1. Structure–activity studies showed that the methyl group was unimportant for activity, and that the potencies of these inhibitors could be best improved by shortening the length of the mercaptoalkanoyl side-chain. Replacing the thiol group with a carboxylic acid led to complete loss of activity, and extending the length of the carboxylate group led to decreased potency. Good activity could be maintained by substituting the proline ring with pipecolic acid.
Addition of organolithium reagents to Ahc methyl ester. An approach to new α-amino ketones
Avenoza, Alberto,Busto, Jesús H.,Peregrina, Jesús Manuel
, p. 10167 - 10171 (2002)
We have developed a versatile methodology to obtain α-amino ketones by acylation of methyl N-benzoyl-7-azabicyclo[2.2.1]heptane-1-carboxylate (1) with organolithium reagents. The reaction proceeds via a stable tetrahedral intermediate. When methyl ester 1 was treated under the same conditions but with a different work up procedure (careful addition of saturated NH4Cl), we observed by 1H NMR spectroscopy that a new compound had appeared in the crude reaction mixture corresponding to a hemiacetal.
Ferulic acid amide derivatives with varying inhibition of amyloid-β oligomerization and fibrillization
Kolaj, Igri,Wang, Yanfei,Ye, Kailin,Meek, Autumn,Liyanage, S. Imindu,Santos, Clarissa,Weaver, Donald F.
supporting information, (2021/07/07)
Alzheimer's disease (AD) is a progressive neurodegenerative disorder characterized, in part, by the misfolding, oligomerization and fibrillization of amyloid-β (Aβ). Evidence suggests that the mechanisms underpinning Aβ oligomerization and subsequent fibrillization are distinct, and may therefore require equally distinct therapeutic approaches. Prior studies have suggested that amide derivatives of ferulic acid, a natural polyphenol, may combat multiple AD pathologies, though its impact on Aβ aggregation is controversial. We designed and synthesized a systematic library of amide derivatives of ferulic acid and evaluated their anti-oligomeric and anti-fibrillary capacities independently. Azetidine tethered, triphenyl derivatives were the most potent anti-oligomeric agents (compound 2i: IC50 = 1.8 μM ± 0.73 μM); notably these were only modest anti-fibrillary agents (20.57% inhibition of fibrillization), and exemplify the poor correlation between anti-oligomeric/fibrillary activities. These data were subsequently codified in an in silico QSAR model, which yielded a strong predictive model of anti-Aβ oligomeric activity (κ = 0.919 for test set; κ = 0.737 for validation set).
COMPOUNDS, COMPOSITIONS AND METHODS FOR STABILIZING TRANSTHYRETIN AND INHIBITING TRANSTHYRETIN MISFOLDING
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Paragraph 0854-0857, (2021/08/06)
Provided herein are compounds having activity against TTR related conditions, and pharmaceutically accepted salts and solvates thereof. Also provided are methods of using the compounds for inhibiting and preventing TTR aggregation and/or amyloid formation in the peripheral nerves, kidney, cardiac tissue, eye and CNS, and of treating a subject with peripheral TTR amyloidosis.
METHODS OF TREATING PAINFUL DIABETIC PERIPHERAL NEUROPATHY
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Paragraph 0161-0163, (2021/05/14)
Provided herein are methods of treating painful diabetic peripheral neuropathy, such as advanced painful DPN, in a patient by administering to the patient an effective amount of NYX-2925 or a pharmaceutically acceptable salt thereof. Also provided are crystalline forms of 3-hydroxy-2-(5-isobutyryl-1-oxo-2,5-diazaspiro[3,4]octan-2-yl)butanamide.
