74733-26-9Relevant articles and documents
Diverse ortho-C(sp2)-H functionalization of benzaldehydes using transient directing groups
Liu, Xi-Hai,Park, Hojoon,Hu, Jun-Hao,Hu, Yan,Zhang, Qun-Liang,Wang, Bao-Long,Sun, Bing,Yeung, Kap-Sun,Zhang, Fang-Lin,Yu, Jin-Quan
supporting information, p. 888 - 896 (2017/05/16)
Pd-catalyzed C-H functionalizations promoted by transient directing groups remain largely limited to C-H arylation only. Herein, we report a diverse set of ortho-C(sp2)-H functionalizations of benzaldehyde substrates using the transient directing group strategy. Without installing any auxiliary directing group, Pd(II)-catalyzed C-H arylation, chlorination, bromination, and Ir(III)-catalyzed amidation, could be achieved on benzaldehyde substrates. The transient directing groups formed in situ via imine linkage can override other coordinating functional groups capable of directing C-H activation or catalyst poisoning, significantly expanding the scope for metal-catalyzed C-H functionalization of benzaldehydes. The utility of this approach is demonstrated through multiple applications, including late-stage diversification of a drug analogue.
Design, synthesis, and structure-activity relationship of a novel series of GluN2C-selective potentiators
Zimmerman, Sommer S.,Khatri, Alpa,Garnier-Amblard, Ethel C.,Mullasseril, Praseeda,Kurtkaya, Natalie L.,Gyoneva, Stefka,Hansen, Kasper B.,Traynelis, Stephen F.,Liotta, Dennis C.
, p. 2334 - 2356 (2014/04/17)
NMDA receptors are tetrameric complexes composed of GluN1 and GluN2A-D subunits that mediate a slow Ca2+-permeable component of excitatory synaptic transmission. NMDA receptors have been implicated in a wide range of neurological diseases and thus represent an important therapeutic target. We herein describe a novel series of pyrrolidinones that selectively potentiate only NMDA receptors that contain the GluN2C subunit. The most active analogues tested were over 100-fold selective for recombinant GluN2C-containing receptors over GluN2A/B/D-containing NMDA receptors as well as AMPA and kainate receptors. This series represents the first class of allosteric potentiators that are selective for diheteromeric GluN2C-containing NMDA receptors.
Heterobiaryl human immunodeficiency virus entry inhibitors
Lu, Rong-Jian,Tucker, John A.,Pickens, Jason,Ma, You-An,Zinevitch, Tatiana,Kirichenko, Olga,Konoplev, Vitalii,Kuznetsova, Svetlana,Sviridov, Sergey,Brahmachary, Enugurthi,Khasanov, Alisher,Mikel, Charles,Yang, Yang,Liu, Changhui,Wang, Jian,Freel, Stephanie,Fisher, Shelly,Sullivan, Alana,Zhou, Jiying,Stanfield-Oakley, Sherry,Baker, Brian,Sailstad, Jeff,Greenberg, Michael,Bolognesi, Dani,Bray, Brian,Koszalka, Barney,Jeffs, Peter,Jeffries, Cynthia,Chucholowski, Alexander,Sexton, Connie
supporting information; experimental part, p. 4481 - 4487 (2010/03/01)
Previously disclosed HIV (human immunodeficiency virus) attachment inhibitors, exemplified by BMS 806 (formally BMS378806, 1), are characterized by a substituted indole or azaindole ring linked to a benzoylpiperazine via a ketoamide or sulfonamide group. In the present report, we describe the discovery of a novel series of potent HIV entry inhibitors in which the indole or azaindole ring of previous inhibitors is replaced by a heterobiaryl group. Several of these analogues exhibited IC50 values of less than 5 nM in a pseudotyped antiviral assay, and compound 13k was demonstrated to exhibit potency and selectivity similar to those of 1 against a panel of clinical viral isolates. Moreover, current structure-activity relationship studies of these novel biaryl gp120 inhibitors revealed that around the biaryl, a fine crevice might exist in the gp120 binding site. Taken in sum, these data reveal a hitherto unsuspected flexibility in the structure-activity relationships for these inhibitors and suggest new avenues for exploration and gp120 inhibitor design. 2009 American Chemical Society.
