203866-16-4Relevant articles and documents
Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB)
Tatum, Natalie J.,Yufit, Dmitry S.,Cobb, Steven L.,Coxon, Christopher R.
, p. 77 - 83 (2015)
Herein we report the first X-ray crystal structure of the well-known (S)-l-ala-Ni-BPB complex (1) and compare this with the X-ray crystal structures obtained for two novel fluorinated (S)-l-ala-Ni-BPB complexes (8 and 12) that contain either an S- or R-fluorine atom on the proline ring of the BPB ligand. The preparation of complexes 8 and 12 has been enabled by the synthesis of two new fluorinated BPB ligands (7 and 11). In this work we looked to observe the structural effects that the introduction of a single fluorine atom had on the known complex 1. Arising from this, we highlight a novel fluorine-nickel interaction that on the basis of DFT calculations appears to provide additional stabilization to one of the complexes prepared ((S)-l-ala-Ni-BPB complex 8).
Novel Tricyclic Pyroglutamide Derivatives as Potent RORγt Inverse Agonists Identified using a Virtual Screening Approach
Liu, Qingjie,Batt, Douglas G.,Weigelt, Carolyn A.,Yip, Shiuhang,Wu, Dauh-Rurng,Ruzanov, Max,Sack, John S.,Wang, Jinhong,Yarde, Melissa,Li, Sha,Shuster, David J.,Xie, Jenny H.,Sherry, Tara,Obermeier, Mary T.,Fura, Aberra,Stefanski, Kevin,Cornelius, Georgia,Khandelwal, Purnima,Tino, Joseph A.,Macor, John E.,Salter-Cid, Luisa,Denton, Rex,Zhao, Qihong,Dhar, T. G. Murali
supporting information, p. 2510 - 2518 (2020/12/03)
Employing a virtual screening approach, we identified the pyroglutamide moiety as a nonacid replacement for the cyclohexanecarboxylic acid group which, when coupled to our previously reported conformationally locked tricyclic core, provided potent and selective RORγt inverse agonists. Structure-activity relationship optimization of the pyroglutamide moiety led to the identification of compound 18 as a potent and selective RORγt inverse agonist, albeit with poor aqueous solubility. We took advantage of the tertiary carbinol group in 18 to synthesize a phosphate prodrug, which provided good solubility, excellent exposures in mouse PK studies, and significant efficacy in a mouse model of psoriasis.
Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor
González-Esguevillas, María,Miró, Javier,Jeffrey, Jenna L.,MacMillan, David W.C.
, p. 4222 - 4227 (2019/06/13)
Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.
