54705-19-0Relevant academic research and scientific papers
Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
Rotondi, Giulia,Guglielmi, Paolo,Carradori, Simone,Secci, Daniela,De Monte, Celeste,De Filippis, Barbara,Maccallini, Cristina,Amoroso, Rosa,Cirilli, Roberto,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
, p. 1400 - 1413 (2019/08/26)
A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.
An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent
Pinna, Giovanni,Bellucci, Maria Cristina,Malpezzi, Luciana,Pisani, Laura,Superchi, Stefano,Volonterio, Alessandro,Zanda, Matteo
, p. 5268 - 5281 (2011/08/06)
N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.
Synthesis of 1-aryl-tetralins and 4-aryl-benzopyrans by sulfoxide-mediated benzylic carbocation cyclizations
Volonterio, Alessandro,Zanda, Matteo
, p. 8723 - 8726 (2007/10/03)
An alkylation/cyclization sequence, with both steps mediated by the ortho-N-methylformamido-phenylsulfinyl function, provided two new C-C bonds and an efficient entry to 1-aryl-tetralins and 4-aryl-benzopyrans. Scope and limits of the process have been studied in detail.
An umpolung sulfoxide reagent as α-hydroxy and α-chloro benzyl carbanion equivalents
Volonterio, Alessandro,Bravo, Pierfrancesco,Zanda, Matteo
, p. 6537 - 6540 (2007/10/03)
ortho-[(N-Methyl)carbamoyl]phenyl benzyl sulfoxide is used as a synthetic equivalent of α-hydroxy and α-chloro benzyl carbanions by means of a two-step sequence involving (1) highly stereoselective α-C-alkylation with alkyl bromides, and (2) displacement of the sulfinyl group by an OH or a Cl under Pummerer or chloro-Pummerer conditions, respectively. The sulfinyl auxiliary can be effectively regenerated and recycled.
A novel cyclization reaction of o-carboxyphenyl and o-carbamoylphenyl sulfoxides. Formation of benzoxathiane, dihydrobenzothiazine and benzoisothiazoline derivatives
Oae,Numata
, p. 2641 - 2646 (2007/10/08)
When o-carboxyphenyl or o-carbamoylphenyl sulfoxide was heated with a large excess of acetic anhydride at 100-130° for 1-3 h, 6-membered heterocyclic compounds, i.e., 3,1 - benzoxathian-4 - one and 2,3 - dihydro - 1,3 - benzothiazin - 4 - one, and a 5-membered heterocyclic compound, i.e., 1,2-benzoisothiazolin-3-one were obtained in good yield. Cyclization would take place by the initial intramolecular nucleophilic attack of either the sulfinyl O atom at ortho-carbonyl carbon or the N atom of the amide group at ortho-sulfinyl S atom to give a 5-membered cyclic acyloxysulfonium salt or aminosulfonium salt, which undergoes an intramolecular Pummerer rearrangement to afford the heterocyclic compounds.
