- Chemoselective and Kilogram-Scale Synthesis of Acetanilide β3-Adrenergic Receptor Agonist
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We describe an alternative route for the synthesis of β3-adrenergic receptor agonist (S)-2-(2-phenylamino-1,3- thiazol-4-yl)-4′-{2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl}acetanilide (1). The key intermediate (S)-1-{[2-(4-aminophenyl)ethyl]amin
- Kawazoe, Souichirou,Suzuki, Takayuki,Nakamura, Hirofumi,Sugimori, Toshiyuki,Onda, Kenichi,Maruyama, Tatsuya,Okada, Minoru
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p. 139 - 145
(2015/01/30)
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- Synthesis and evaluation of novel phenoxypropanolamine derivatives containing acetanilides as potent and selective β3-adrenergic receptor agonists
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In the search for potent and selective human β3-adrenergic receptor (AR) agonists as potential drugs for the treatment of obesity and noninsulin-dependent (type II) diabetes, a novel series of phenoxypropanolamine derivatives containing acetanilides were prepared and their biological activities were evaluated at the human β3-, β2-, and β1-ARs. Several of the analogues (21a, 21b, and 27a) exhibited potent agonistic activity at the β3-AR. Among the compounds described herein, the N-methyl-1-benzylimidazol-2-ylacetanilide derivative (21b) was found to be the most potent and selective β3-AR agonist, with an EC50 value of 0.28 μM and no agonistic activity for either the β1- or β2-AR. In addition, 21b showed significant hypoglycemic activity in a rodent diabetic model.
- Maruyama, Tatsuya,Onda, Kenichi,Hayakawa, Masahiko,Seki, Norio,Takahashi, Takumi,Moritomo, Hiroyuki,Suzuki, Takayuki,Matsui, Tetsuo,Takasu, Toshiyuki,Nagase, Itsuro,Ohta, Mitsuaki
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experimental part
p. 3283 - 3294
(2009/09/08)
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- Discovery of a novel, potent and selective human β3- adrenergic receptor agonist
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Design and structure-activity relationships of a novel β3- adrenergic receptor agonist are described. The discovery of a novel, potent and selective β3-adrenergic receptor (AR) agonist is described. SAR studies demonstrated the struc
- Nakajima, Yutaka,Hamashima, Hitoshi,Washizuka, Ken-Ichi,Tomishima, Yasuyo,Ohtake, Hiroaki,Imamura, Emiko,Miura, Toshiko,Kayakiri, Hiroshi,Kato, Masayuki
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p. 251 - 254
(2007/10/03)
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- Amide derivatives and medicinal compositions thereof
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PCT No. PCT/JP98/00237 Sec. 371 Date May 7, 1999 Sec. 102(e) Date May 7, 1999 PCT Filed Jan. 22, 1998 PCT Pub. No. WO98/32742 PCT Pub. Date Jul. 30, 1998An amide derivative represented by the following general formula (I) or a salt thereof and a pharmaceutical composition containing the amide derivative and a pharmaceutically acceptable vehicle. (The symbols in the formula have the following meanings. (wherein A: heteroarylene; X: bond, O, S, -NR5-, -NR5CO-, -NR5CONH-, -NR5SO2- or -NR5C(=NH)NH-; R1: -H, -optionally substituted lower alkyl, -optionally substituted aryl, -optionally substituted heteroaryl or -optionally substituted cycloalkyl; R2a, R2b: -H or -lower alkyl, which may be the same or different; R3: -H or -lower alkyl; R4a, R4b: -H or -OH, which may be the same different, or R4a and R4b are taken together to form =O or =N DIFFERENCE O-lower alkyl; and R5: -H or -lower alkyl.
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