226396-71-0Relevant articles and documents
Synthesis of Sulfones via Ru(II)-Catalyzed Sulfination of Boronic Acids
Gulbe, Krista,Turks, Mā ris
, p. 5660 - 5669 (2020/05/19)
Ruthenium(II) complexes catalyze the insertion of sulfur dioxide into (het)aryl and alkenyl boronic acids. The transmetalation-sulfination process proceeds with DABSO in the presence of 5 mol % RuCl2(PPh3)3 in methanol at 100 °C. The intermediate sulfinate salt can be quenched with various electrophiles such as alkyl halides, epoxides, Michael acceptors, and λ3-iodanes in moderate to good yields. The reported sulfone synthesis can be performed either as a direct one-pot or one-pot two-step procedure depending on the reactivity of the electrophile.
Discovery and Preclinical Characterization of 3-((4-(4-Chlorophenyl)-7-fluoroquinoline-3-yl)sulfonyl)benzonitrile, a Novel Non-acetylenic Metabotropic Glutamate Receptor 5 (mGluR5) Negative Allosteric Modulator for Psychiatric Indications
Galambos, János,Bielik, Attila,Krasavin, Mikhail,Orgován, Zoltán,Domány, Gy?rgy,Nógrádi, Katalin,Wágner, Gábor,Balogh, Gy?rgy T.,Béni, Zoltán,Kóti, János,Szakács, Zoltán,Bobok, Amrita,Kolok, Sándor,Mikó-Bakk, Mónika L.,Vastag, Mónika,Sághy, Katalin,Laszy, Judit,Halász, Attila Sándor,Balázs, Ottilia,Gál, Krisztina,Greiner, István,Szombathelyi, Zsolt,Keser?, Gy?rgy M.
, p. 2470 - 2484 (2017/04/03)
Negative allosteric modulators (NAM) of metabotropic glutamate receptor 5 (mGluR5) have been implicated as a potential pharmacotherapy for a number of psychiatric diseases, including anxiety and depression. Most of the mGluR5 NAM clinical candidates can be characterized by the central acetylenic moiety that connects the terminal pharmacophores. Identification of a sulfoquinoline hit via high throughput screening (HTS) followed by optimization provided a 4-phenyl-3-aryl-sulfoquinoline lead compound with the minimal pharmacophore. Optimization of the core and aryl appendages was performed by scanning and matrix libraries synthesized by the multiple parallel synthesis approach. Biological evaluation of matrix libraries provided a number of potent, metabolically stable, and in vivo active compounds. One of these compounds, 25 showed high efficacy and safety in preclinical in vivo models; this allowed its nomination as a novel, nonacetylenic mGluR5 NAM clinical candidate. Compound 25 was advanced to first-in-man trials for the treatment of psychiatric conditions.
Synthesis and structure-activity relationships of β- and α-piperidine sulfone hydroxamic acid matrix metalloproteinase inhibitors with oral antitumor efficacy
Becker, Daniel P.,Villamil, Clara I.,Barta, Thomas E.,Bedell, Louis J.,Boehm, Terri L.,DeCrescenzo, Gary A.,Freskos, John N.,Getman, Daniel P.,Hockerman, Susan,Heintz, Robert,Howard, Susan Carol,Li, Madeleine H.,McDonald, Joseph J.,Carron, Chris P.,Funckes-Shippy, Chris L.,Mehta, Pramod P.,Munie, Grace E.,Swearingen, Craig A.
, p. 6713 - 6730 (2007/10/03)
α-Piperidine-β-sulfone hydroxamate derivatives were explored that are potent for matrix metalloproteinases (MMP)-2, -9, and -13 and are sparing of MMP-1. The investigation of the β-sulfones subsequently led to the discovery of hitherto unknown α-sulfone h
