51479-73-3Relevant articles and documents
A simple access to trichloroacetimidates
Patil, Vijay J.
, p. 1481 - 1484 (1996)
O - Trichloroacetimidates can be prepared, under mild conditions in high yield and high purity, by reacting the substrate with trichloroacetonitrile in dichloromethane and 50% aqueous potassium hydroxide mixture containing a catalytic amount of tetra-n-butylammonium hydrogen sulfate.
Cp?Rh(III)-Catalyzed Low Temperature C-H Allylation of N-Aryl-trichloro Acetimidamide
Debbarma, Suvankar,Bera, Sourav Sekhar,Maji, Modhu Sudan
, p. 11716 - 11725 (2016/12/09)
The readily synthesized trichloro acetimidamide was found to be an excellent directing group for the directed C-H-allylation reactions. Depending on the allylating agent used, selectively either mono- or diallylated products were readily synthesized. More
Synthesis, in vitro pharmacology, structure - Activity relationships, and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6- dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists
Nakazato, Atsuro,Sakagami, Kazunari,Yasuhara, Akito,Ohta, Hiroshi,Yoshikawa, Ryoko,Itoh, Manabu,Nakamura, Masato,Chaki, Shigeyuki
, p. 4570 - 4587 (2007/10/03)
Novel group II metabotropic glutamate receptor (mGluR) antagonists, 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives 11 and 12, were discovered by the incorporation of a hydroxy or alkoxyl group onto the C-3 portion of selective and potent group II mGluR agonist 5, (1R,2S,5R,6R)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid. Among these compounds, (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6- fluorobicyclo-[3.1.0]hexane-2,6-dicarboxylic acid (-)-11be (MGS0039) was a highly selective and potent group II mGluR antagonist with the best pharmacokinetic profile. Compound (-)-11be exhibited high affinities for mGlu 2 (Ki = 2.38 ± 0.40 nM) and mGlu 3 (4.46 ± 0.31 nM) but low affinity for mGluR 7 (Ki = 664 ± 106 nM), and potent antagonist activities for mGlu 2 (IC50 = 20.0 ± 3.67nM) and mGluR 3 (IC50 = 24.0 ± 3.54 nM) but much less potent antagonist activities for mGlu 4 (IC50 = 1740 ± 1080 nM), mGlu 6 (IC50 = 2060 ± 1270 nM), mGlu 1 (IC50 = 93300 ± 14600 nM), and mGluR 5 (IC50 = 117000 ± 38600 nM). No significant agonist activities of (-)-11be were found for mGluRs 2, 3, 4, 6, 1, and 5 (EC50 > 100000 nM). Furthermore, (-)-11be exhibited dose-dependent oral absorption (plasma Cmax: 214 ± 56.7, 932 ± 235, and 2960 ± 1150 ng/mL for 3 mg/kg, 10 mg/kg, and 30 mg/kg, po, respectively) and acceptable blood-brain barrier penetration (brain C max: 13.2 ng/mL for 10 mg/kg, po 6 h). In this paper, we report the synthesis, in vitro pharmacological profile, and structure-activity relationships (SARs) of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6- dicarboxylic acid derivatives 11 and 12, and pharmacokinetic profiles of several typical compounds.
