39184-82-2Relevant academic research and scientific papers
Study of the structural and conformational properties of fluoro-substituted thioacetanilide derivatives
Domínguez, Rodrigo E.,Iriarte, Ana G.,Lezama, José Osvaldo Guy,Robles, Norma Lis
, (2020/07/30)
The assessment of the influence of a halogen atom in the structural, vibrational and conformational properties of o-, m- and p-fluorothioacetanilide derivatives was achieved through different methodologies. For all compounds infrared (FTIR) and nuclear ma
Atropisomeric 4-phenyl-4 H -1,2,4-triazoles as selective glycine transporter 1 inhibitors
Sugane, Takashi,Tobe, Takahiko,Hamaguchi, Wataru,Shimada, Itsuro,Maeno, Kyoichi,Miyata, Junji,Suzuki, Takeshi,Kimizuka, Tetsuya,Sakamoto, Shuichi,Tsukamoto, Shin-Ichi
, p. 5744 - 5756 (2013/08/23)
We report on the optimization of 4H-1,2,4-triazole derivatives to increase their activity and selectivity as glycine transporter 1 (GlyT1) inhibitors. Structure-activity relationship exploration resulted in the identification of a 3-[3-ethyl-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methylbenzonitrile (14u) compound with markedly higher selectivity for GlyT1. Physiochemical studies revealed that 14u exists as a stable pair of atropisomers under physiological conditions. We successfully separated the atropisomers to obtain active enantiomer (R)-14u, which displayed favorable pharmacokinetic properties, as well as positive results in the mice Y-maze test.
Synthesis and biological evaluation of 3-biphenyl-4-yl-4-phenyl-4 h -1,2,4-triazoles as novel glycine transporter 1 inhibitors
Sugane, Takashi,Tobe, Takahiko,Hamaguchi, Wataru,Shimada, Itsuro,Maeno, Kyoichi,Miyata, Junji,Suzuki, Takeshi,Kimizuka, Tetsuya,Kohara, Atsuyuki,Morita, Takuma,Doihara, Hitoshi,Saita, Kyouko,Aota, Masaki,Furutani, Masako,Shimada, Yoshiaki,Hamada, Noritaka,Sakamoto, Shuichi,Tsukamoto, Shin-Ichi
supporting information; experimental part, p. 387 - 391 (2011/03/18)
We describe the preparation and evaluation of a novel series of glycine transporter 1 (GlyT1) inhibitors derived from a high-throughput screening hit. The SAR studies resulted in the discovery of 3-biphenyl-4-yl-4-(2-fluorophenyl)- 5-isopropyl-4H-1,2,4-tr
One-pot preparation of 2 (alkly)arylbenzothiazoles from the corresponding o-halobenzanilides
Bernardi, Dan,Ba, Lalla A?cha,Kirsch, Gilbert
, p. 2121 - 2123 (2008/02/09)
Thionation of o-halobenzanilides was carried out in the presence of Lawesson's reagent. Subsequently, the formed thioamides reacted with cesium carbonate to give the corresponding benzothiazole derivatives in the same pot. Georg Thieme Verlag Stuttgart.
Synthesis of 2-substituted benzothiazoles from 2-fluorophenylisothiocyanate
Ares
, p. 625 - 633 (2007/10/02)
Treatment of 2-fluorophenylisothiocyanate with a Grignard reagent, followed by base-induced cyclization of the resulting thioamide, provides a convenient method of synthesizing 2-substituted benzothiazoles. Best results are obtained upon isolation and purification of the intermediate thioamide, but a direct one-pot isothiocyanate-to-benzothiazole transformation has also been achieved.
