77147-14-9Relevant academic research and scientific papers
Red-shifted tetra-ortho-halo-azobenzenes for photo-regulated transmembrane anion transport
Bo, Zonghua,Duarte, Fernanda,Kerckhoffs, Aidan,Langton, Matthew J.,Penty, Samuel E.
supporting information, p. 9058 - 9067 (2021/11/04)
Photo-responsive synthetic ion transporters are of interest as tools for studying transmembrane transport processes and have potential applications as targeted therapeutics, due to the possibility of spatiotemporal control and wavelength-dependent function. Here we report the synthesis of novel symmetric and non-symmetric red-shifted tetra-ortho-chloro- and tetra-ortho-fluoro azobenzenes, bearing pendant amine functionality. Functionalisation of the photo-switchable scaffolds with squaramide hydrogen bond donors enabled the preparation of a family of anion receptors, which act as photo-regulated transmembrane chloride transporters in response to green or red light. The subtle effects of chlorine/fluorine substitution,meta/parapositioning of the anion receptors, and the use of more flexible linkers are explored. NMR titration experiments on the structurally diverse photo-switchable receptors reveal cooperative binding of chloride in theZ, but notEisomer, by the two squaramide binding sites. These results are supported by molecular dynamics simulations in explicit solvent and model membranes. We show that this intramolecular anion recognition leads to effective switching of transport activity in lipid bilayer membranes, in which optimalZisomer activity is achieved using a combination of fluorine substitution andpara-methylene spacer units.
COMPOSITIONS FOR PROMOTING READTHROUGH OF PREMATURE TERMINATION CODONS, AND METHODS OF USING THE SAME
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Page/Page column 323; 234, (2017/04/11)
Disclosed are compounds of general formula (I) that promote readthrough of a premature termination codon (PTC) of an RNA molecule in a translation system, and their use, alone or in combination with other compounds, such as aminoglycoside, to treat diseases or disorders ameliorated by modulation of a premature termination codon (PTC) of an RNA molecule in a translation system. The disorder or disease may be Dystrophic epidermolysis bullosa, Batten disease, Duchenne muscular dystrophy, cancer, and spinal muscular atrophy. Ar-L-B (I)
Characterization of novel aminobenzylcantharidinimides and related imides by proton NMR spectra and their effects on NO induction
Tseng, Ing-Jy,Lin, Pen-Yuan,Sheu, Shiow-Yunn,Tung, Wan-Ni,Lin, Ching-Tung,Lin, Mei-Hsiang
, p. 59 - 63 (2015/02/19)
Various acidic anhydrides including cantharidin were converted into corresponding aminobenzylcantharidinimide 3a and analogous imides 3b~k (at the ortho, meta, and para positions) with 35%~87% yields by reacting with aminobenzylamines and triethylamine. The two methyl side chains of cantharidinimides 3ao, 3am, and 3ap, and related imides had more than two chiral centers; the lone pair of electrons of nitrogen displayed a different chemical shift and coupling constant in H-NMR spectra when the amino group of benzylamine was in the ortho position. These cantharidinimides had parent aniline, pyridine, and naphthalene plane structures, and the primary amine nucleophilicity and basicity might reflect the inductive electron's negative effect on chemical shifts. We prepared cantharidinimides by heating the reactants cantharidin 1a, aliphatic and aromatic acid anhydrides, primary benzylic amines, and aniline derivatives to ca. 200 °C with 3 mL of dry toluene, and 1~2 mL of triethylamine in high-pressure sealed tubes (Buchi glasuster 0032) to produce cantharidinimides and their analogues in good yields. The para-aminobenzylic imides showed greater inhibition of nitric oxide (NO) synthesis by NO synthase (NOS) than did ortho- and meta-aminobenzylic imides. Compound 3fp, para-aminobenzylic norbonane-imide, had the most potent effect on inducible NOS among the tested compounds and showed 35% inhibition. Cantharidinimides and their analogue were prepared by heating the reactants cantharidin, aliphatic, aromatic acid anhydrides, and primary benzyl amines, aniline derivatives with 3 mL of dry toluene, and 1-2 mL of triethylamine in high-pressure sealed tube at 200 oC in good yields. The para-aminobenzylic imides showed greater inhibition of nitric oxide (NO) synthesis by NO synthase (NOS) than that of ortho- and meta-aminobenzylic imides did.
4-PHENYLAMINO-PYRIMIDINE DERIVATIVES HAVING PROTEIN KINASE INHIBITOR ACTIVITY
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Page/Page column 19, (2012/10/18)
The invention relates compounds of general formula (I) and pharmaceutically acceptable salts and solvates thereof wherein R1 is halogen, vinylene-aryl, substituted aryl, heteroaryl or a benzo[1,3]dioxolil group,W is a group of formula —NH—SO2—R2 or heteroaryl group or NHR3 group where R3 is hydrogen or heteroaryl; and n is 1, 2, 3 or 4. Furthermore, the present invention is directed to pharmaceutical composition containing at least one compound of general formula (I) and/or pharmaceutically acceptable salts or solvates thereof and for the use of them for the preparation of pharmaceutical compositions for the prophylaxis and/or the treatment of protein kinase related, especially CDK9-related diseases e.g. cell proliferative disease, infectious disease, pain, cardiovascular disease and inflammation.
4-PHENYLAMINO-PYRIMIDINE DERIVATIVES HAVING PROTEIN KINASE INHIBITOR ACTIVITY
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Page/Page column 32, (2011/07/09)
The invention relates compounds of general formula (I) and pharmaceutically acceptable salts and solvates thereof wherein R1 is halogen, vinylene-aryl, substituted aryl, heteroaryl or a benzo[1,3]dioxolil group, W is a group of formula -NH-SO2-R2 or heteroaryl group or NHR3 group where R3 is hydrogen or heteroaryl; and n is 1, 2, 3 or 4. Furthermore, the present invention is directed to pharmaceutical composition containing at least one compound of general formula (I) and/or pharmaceutically acceptable salts or solvates thereof and for the use of them for the preparation of pharmaceutical compositions for the prophylaxis and/or the treatment of protein kinase related, especially CDK9-related diseases e.g. cell proliferative disease, infectious disease, pain, cardiovascular disease and inflammation.
A Comparison of the Reactions of Some Ethyl N-Arylcarbamates with Those of the Corresponding Acetanilides. II Amidomethylation with N-Hydroxymethylphthalimide
Rosevear, Judi,Wilshire, John F. K.
, p. 339 - 353 (2007/10/02)
The reactions of some ethyl N-arylcarbamates and of the corresponding acetanilides towards 1 equiv. of N-hydroxymethylphthalimide in concentrated sulfuric acid at 50 deg C have been compared with one another.In the case of certain para-substituted compoun
