56766-90-6Relevant academic research and scientific papers
Regioselection in the synthesis of 4-benzyltetral-1-ones and the new 4-arylbenzosuber-1-ones
Truong, Daniel,Howard, Brittany L.,Thompson, Philip E.
, (2021)
The intramolecular Friedel-Crafts acylation of 4,5-diarylpentanoic acids has the possibility to cyclise to either a 6-membered ring to give 4-benzyltetral-1-one or a 7-membered ring to give 4-arylbenzosuber-1-one. Of these, only the former compound class has previously been reported. The impact of the substituents positioning on the outcome of the cyclisation has been investigated. The complete formation of either the tetralone or the benzosuberone regioisomer was possible under the same reaction conditions, dependent upon the ring activation and/or deactivation of the chosen substituents. Selected bromo or methoxy substituents could be used as auxiliaries, included in precursors to afford the desired regioisomer and then subsequently removed.
On the synthesis and biological properties of isocombretastatins: A case of ketone homologation during Wittig reaction attempts
Stocker, Vivien,Ghinet, Alina,Leman, Marie,Rigo, Benoit,Millet, Regis,Farce, Amaury,Desravines, Deborah,Dubois, Joelle,Waterlot, Christophe,Gautret, Philippe
, p. 3683 - 3696 (2013/04/11)
New isocombretastatins were synthesized by reacting the corresponding phenstatin analogs with CH3PPh3Br in presence of tBuOK. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization. In particular, monomethoxylated derivatives of phenstatin and isoCA-4 exhibit similar activities to those of parent phenstatin. Attempts of the Wittig reaction on 2- (or 4-) methoxy-4′-nitrobenzophenones in the same conditions do not lead to the expected isocombretastatins but to methyleneketones with the exclusion of triphenylphosphine. A mechanism for this new ketone homologation was proposed.
A simple route to new phenanthro- and phenanthroid-fused thiazoles by a PIFA-mediated (hetero)biaryl coupling reaction
Moreno, Isabel,Tellitu, Imanol,Dominguez, Esther,SanMartin, Raul
, p. 2126 - 2135 (2007/10/03)
An application of the PIFA-mediated [PIFA: phenyliodine(III) bis(trifluoroacetate) biaryl coupling reaction is presented and extended to the formation of heterobiaryl connections. A preliminary study of the scope and limitations of this procedure was carried out in the synthesis of phenanthroids 11 from a series of phenethyl-substituted heterocycles 10, It was observed that in some cases a competitive dimerization process took place. It was also found that the coupling step could be efficiently extended to a larger number of examples if an aromatic ring were situated fused to the 1,2-diarylethane skeleton, as in 23 and 30. The synthesis of a series of 4,5-diarylthiazoles 23a-g was therefore carried out to explore the electronic requirements and the regioselectivity of the PIFA-mediated non-phenolic coupling reaction. When the same procedure was applied to aryl-heteroarylthiazoles 30, a series of phenanthroid-fused thiazoles 31 was obtained in good overall yields. To the best of our knowledge, no oxidative aryl-heteroaryl coupling reaction of this type had previously been reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Catechol based inhibitors of 15-lipoxygenase
Tait, Bradley D.,Dyer, Richard D.,Auerbach, Bruce J.,Bornemeier, Dirk,Guilds-Zamarka, Linda,Oxender, Maritza,Roth, Bruce D.,Trivedi, Bharat K.,Cornicelli, Joseph A.
, p. 93 - 96 (2007/10/03)
A potent 15-lipoxygenase (15-LO) inhibitor, compound 6, was identified by mass screening the Parke-Davis compound portfolio. The active moiety of compound 6 was determined to be the catechol functionality. Additional analogs were prepared and analyzed for inhibitory activity against 5-, 12-, and 15-lipoxygenase.
The Rotational and Configurational Isomerism of N-(Monosubstituted ethyl)-amides by Nuclear Magnetic Resonance
Aguirre, Jose M.,Ibanez, Adriana F.,Alesso, Elba N.,Tombari, Dora G.,Iglesias, Graciela Y. Moltrasio
, p. 2802 - 2807 (2007/10/02)
Several N-(monosubstituted ethyl)amides were synthesized and their carbon and proton nuclear magnetic resonance (13C and 1H-NMR) spectra were determined.Both (Z) and (E) stereoisomers could be observed in the formamides, but only the (Z) isomer was identi
o-Aminophenyl Alkyl/Aralkyl Ketones and Their Derivatives: Part IV - Synthesis of 4-Benzyl-6,7-dimethoxyquinazoline
Kamath, H. V.,Dhekne, Vijay V.,Kulkarni, Sheshgiri N.
, p. 911 - 913 (2007/10/02)
o-Nitrophenyl benzyl ketones (II) have been exclusively synthesised from the corresponding substituted α-(o-nitroaroyl)arylacetaldehydes by the acid-catalysed deformylation.Nitration of deoxybenzoins having one of the benzene nuclei activated, such as the
