373-28-4Relevant articles and documents
C-F bond substitution via aziridinium ion intermediates
Tr?ff,Janjetovic,Hilmersson
supporting information, p. 13260 - 13263 (2015/08/24)
Aliphatic 1,2-aminofluorides undergo extremely fast substitution reactions under the influence of lanthanum tris(hexamethyldisilazide). The substitution proceeds via an in situ generated aziridinium ion intermediate, which subsequently undergoes ring opening by addition of a nucleophile, yielding various β-substituted amines.
Benzoxazinones as PPARγ Agonists. 2. SAR of the Amide Substituent and In Vivo Results in a Type 2 Diabetes Model
Rybczynski, Philip J.,Zeck, Roxanne E.,Dudash Jr., Joseph,Combs, Donald W.,Burris, Thomas P.,Yang, Maria,Osborne, Melville C.,Chen, Xiaoli,Demarest, Keith T.
, p. 196 - 209 (2007/10/03)
A series of benzoxazinones has been synthesized and tested for PPARγ agonist activity. Synthetic approaches were developed to provide either racemic or chiral compounds. In vitro functional potency could be measured through induction of the aP2 gene, a target of PPARγ. These studies revealed that compounds with large aliphatic chains at the nitrogen of the benzoxazinone were the most potent. Substitution of the chain was tolerated and in many cases enhanced the in vitro potency of the compound. Select compounds were further tested for metabolic stability, oral bioavailability in rats, and efficacy in db/db mice after 11 days of dosing. In vivo analysis with 13 and 57 demonstrated that the series has potential for the treatment of type 2 diabetes.
Biologically active 4H-benzo [1,4]oxazin-3-ones
-
, (2008/06/13)
The invention is directed to 4h-benzo[1,4]oxazin-3-ones useful as peroxisome proliferator activated receptor gamma (PPARγ) agonists or antagonists. Pharmaceutical compositions comprising compounds of the present invention and methods of treating conditions such as NIDDM and obesity are also disclosed.