54640-04-9Relevant academic research and scientific papers
Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu
supporting information, p. 7443 - 7449 (2020/10/09)
We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.
Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV
Carta, Fabrizio,Vullo, Daniela,Maresca, Alfonso,Scozzafava, Andrea,Supuran, Claudiu T.
supporting information, p. 1564 - 1569 (2013/04/10)
Using hydroxy-/dihydroxybenzoic acids as leads, a series of methyl, ethyl and iso-propyl esters of 4-hydroxy-benzoic acid, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acids and of coumaric acid, were obtained and investigated for the inhibition of six mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms, that is, the cytosolic CA I, II and VII, and the transmembrane CA IX, XII and XIV, many of which are established drug targets. Other compounds incorporating phenol/catechol moieties were obtained from dopamine by reaction with fluorescein isothiocyanate or with 2,4,6-trisubstituted pyrylium salts. Some aminophenols were also derivatized in a similar manner, by using pyrylium salts. Many of these compounds showed increased inhibitory action compared to the lead compounds from which they were obtained, with efficacy in the submicromolar range against most investigated CA isoforms. As phenols are a class of less investigated CA inhibitors (CAIs) compared to the sulfonamides, and their mechanism of inhibition is less well understood, compounds of the type designed here may be helpful in gaining more insights into these phenomena.
A NEW MACROCYCLIC DIACID WITH BALANCED CONFORMATIONAL FLEXIBILITY AND PREORGANIZATION
Gennari, Cesare,Molinari, Francesco,Bartoletti, Marcella,Potenza, Donatella
, p. 279 - 282 (2007/10/02)
Macrocyclic diacid 1 was designed and synthesized as an effective catalyst for hemiacetal cleavage.Molecular modelling studies (using Clark Still's MacroModel) show that 1 has many accessible low energy conformations with various degrees of carboxyl group
Acceleration of Hemiacetal Cleavage through Hydrogen Bonding: A New Synthetic Catalyst with Balanced Conformational Flexibility and Preorganization
Gennari, Cesare,Molinari, Francesco,Bartoletti, Marcella,Piarulli, Umberto,Potenza, Donatella
, p. 3201 - 3203 (2007/10/02)
Hemiacetal cleavage catalyst 1 was designed, synthesized, and shown to be effective in promoting glycolaldehyde dimer dissociation and tetramethylglucose mutarotation.
