1577-04-4Relevant academic research and scientific papers
13C NMR spectroscopy of heterocycles: 1-phenyl-3-aryl/t-butyl-5-arylpyrazoles
Hockstedler, Amy N.,Edjah, Beatrice A.,Azhar, Saajid Z.,Mendoza, Hadrian,Brown, Nicole A.,Arrowood, Hayley B.,Clay, Andrew C.,Shah, Anand B.,Duffek, Glenda M.,Cui, Jianmei,Baumstark, Alfons L.
, p. 125 - 131 (2017/04/14)
A series of chalcones 1-12 were converted to pyrazolines (1Pi-12Pi) by reaction with phenylhydrazine followed by DDQ oxidation to produce the corresponding pyrazoles (1Pz-12Pz). Three 1-phenyl-3-t-butyl-5-arylpyrazoles (13Pz-15Pz) were synthesized using an analogous approach. Molecular modeling studies predicted the 5-aryl group of the pyrazoles for both series to have a torsion angle of 52°-54° whereas the 1-phenyl group was predicted to have 35°-37° torsion angles. The 3-aryl group was predicted to be essentially coplanar (-3°) with the pyrazole system in the first series. 13C NMR data for both series, 1Pz-12Pz and 13Pz-15Pz, were collected in DMSO-d6 at 50°C. A plot of the C4 chemical shifts for 1Pz-12Pz versus Hammet constants for 5-aryl substituents yielded a very good linear correlation (R2=0.96) with a slope of 1.5. The chemical shift data for C4 showed little or no dependence on 3-aryl substituents. The result for 13Pz-15Pz, despite only three points, was consistent with the first series results and yielded a ρ value of 2.0. Distal transmission of substituent effects (5-aryl groups) to C4 of the pyrazole system was reduced by roughly 50-60% of that of the analogous planar isoxazole system, but are not consistent with results for the similarly twisted 4-bromoisoxazoles.
ALLOSTERIC INHIBITORS OF ATYPICAL PROTEIN KINASES C
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Paragraph 0090; 0108; 0134, (2015/06/08)
The invention provides specific small molecule compounds that allosterically regulate the activity of atypical protein kinase C, their use as a medicament, and their use in the treatment and prevention of allergic, inflammatory and autoimmune disorders, cancer, hyperproliferation, sepsis, viral and protozoan infections, dementing diseases, metabolic, sclerotic and osteoporotic disorders.
Discovery and optimization of 1,3,5-trisubstituted pyrazolines as potent and highly selective allosteric inhibitors of protein kinase C-χ
Abdel-Halim, Mohammad,Diesel, Britta,Kiemer, Alexandra K.,Abadi, Ashraf H.,Hartmann, Rolf W.,Engel, Matthias
supporting information, p. 6513 - 6530 (2014/10/15)
There is increasing evidence that the atypical protein kinase C, PKCχ, might be a therapeutic target in pulmonary and hepatic inflammatory diseases. However, targeting the highly conserved ATP-binding pocket in the catalytic domain held little promise to
One-pot synthesis of multifunctionalized m-terphenyls
Chang, Meng-Yang,Chan, Chieh-Kai,Lin, Shin-Ying,Wu, Ming-Hao
, p. 9616 - 9624 (2013/10/22)
A facile one-step synthetic protocol toward multifunctionalized m-terphenyls 5 and sulfonyl m-terphenyls 6 is developed from substituted chalcones 1 and allyl sulfone 2 in good yields via a [3C+3C] annulation. The NaH-mediated annulation features transition metal catalyst-free condition. Chalcones 1 with the functional groups tolerance are easily prepared via Claisen-Schmidt condensation of substituted benzaldehydes 3 with acetophenone 4 in a qualitative yield under an aqueous alkaline methanolic solution.
Regioselective synthesis of 3-carbo-5-phosphonylpyrazoles through a one-pot Claisen-Schmidt/1,3-dipolar cycloaddition/oxidation sequence
Martin, Anthony R.,Mohanan, Kishor,Toupet, Loic,Vasseur, Jean-Jacques,Smietana, Michael
experimental part, p. 3184 - 3190 (2011/06/28)
A one-pot reaction involving an aldehyde, a methyl ketone, and the Bestmann-Ohira reagent has been developed for the synthesis of variously substituted 3-carbo-5-phosphonylpyrazoles. Our synthetic methodology features a domino Claisen-Schmidt/1,3-dipolar cycloaddition/oxidation sequence, which leads to the target compounds in excellent yields. We further demonstrated that this unprecedented sequence could also be combined with a copper-catalyzed azide-alkyne cycloaddition in a one-pot, four-step cascade process generating five new bonds and two heterocyclic rings. Copyright
Fast Atom Bombardment Mass Spectroscopy: a Useful Technique for Structural Characterization of Pyrylium, Thiopyrylium, and Pyridinium Cations
Angekis, Francesco De,Doddi, Giancarlo,Ercolani, Gianfranco
, p. 633 - 638 (2007/10/02)
It is shown that fast atom bombardment (f.a.b.) mass spectrometry is well suited of the title compounds (thirty nine examples are given).Glycerol and bis-(2-hydroxyethyl) sulphide appear to be the best matrices.Spectra are characterized by large peaks cor
