3-(3-fluorophenoxy)-N-(4-methyl-1,3-thiazol-2-yl)benzamide | 1147012-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-fluorophenoxy)-N-(4-methyl-1,3-thiazol-2-yl)benzamide
• CAS: 1147012-29-0
• 化学式: C₁₇H₁₃FN₂O₂S
• 分子量: 328.367
• InChiKey: IAQKCWBVBNPUAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  C₁₇H₁₄FN₃O₂S 在 硫酸 、 溶剂黄146 、 sodium nitrite 、 copper(I) oxide 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以6%的产率得到3-(3-fluorophenoxy)-N-(4-methyl-1,3-thiazol-2-yl)benzamide
  参考文献：
  名称：

  Discovery of potent and orally active 3-alkoxy-5-phenoxy-N-thiazolyl benzamides as novel allosteric glucokinase activators

  摘要：

  Identification and synthesis of novel 3-alkoxy-5-phenoxy-N-thiazolyl benzamides as glucokinase activators are described. Removal of an aniline structure of the prototype lead (2a) and incorporation of an alkoxy or phenoxy substituent led to the identification of 3-Isopropoxy-5-[4-(methylsulfonyl) phenoxy]-N(4- methyl-1,3-thiazol-2-yl) benzamide (27e) as a novel, potent, and orally bioavailable GK activator. Rat oral glucose tolerance test indicated that 27e exhibited a glucose-lowering effect after 10 mg/kg oral administration. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.038

文献信息

• Discovery of potent and orally active 3-alkoxy-5-phenoxy-N-thiazolyl benzamides as novel allosteric glucokinase activators
  作者：Tomoharu Iino、Daisuke Tsukahara、Kenji Kamata、Kaori Sasaki、Sumika Ohyama、Hideka Hosaka、Takuro Hasegawa、Masato Chiba、Yasufumi Nagata、Jun-ichi Eiki、Teruyuki Nishimura

  DOI：10.1016/j.bmc.2009.02.038

  日期：2009.4

  Identification and synthesis of novel 3-alkoxy-5-phenoxy-N-thiazolyl benzamides as glucokinase activators are described. Removal of an aniline structure of the prototype lead (2a) and incorporation of an alkoxy or phenoxy substituent led to the identification of 3-Isopropoxy-5-[4-(methylsulfonyl) phenoxy]-N(4- methyl-1,3-thiazol-2-yl) benzamide (27e) as a novel, potent, and orally bioavailable GK activator. Rat oral glucose tolerance test indicated that 27e exhibited a glucose-lowering effect after 10 mg/kg oral administration. (c) 2009 Elsevier Ltd. All rights reserved.