54705-22-5Relevant articles and documents
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.
Electronic effect, steric hindrance, and anchimeric assistance in oxidation of sulphides. Neighbouring-group participation through Sulphur-oxygen nonbonded interaction
Ruff, Ferenc,Kucsman, Arpad
, p. 1123 - 1128 (2007/10/02)
Using a set of sulphides o- and p-XC6H4SMe, the electronic effect, steric hindrance, and anchimeric assistance for electrophilic Cl+ addition by TsNHCI and O-transfer by NalO4 were investigated by a kinetic method. The steric effect and anchimeric assistance of the ortho-substituents were evaluated by comparing the reactivity of ortho- and para-substituted compounds (K = ko/kp). For neighbouringgroup activity the following order was obtained: CH2OH ~ CH2OMe ~ CH2CO2Me CH2CO2H ~ CH2NMe2 CH2C02 - ~ CHO CO2Me ~ CO2H COMe ~ CONH2 C02- Reaction rates show that the anchimeric assistance is governed by an S mellip; 0 or S ... N close contact developed in the transition state between oppositely polarized heteroatoms. Factors controlling neighbouringgroup participation through attractive non-bonded interactions are discussed.
