1-(6-甲氧基-1,3-苯并噻唑-2-基)乙酮 | 65840-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 1-(6-甲氧基-1,3-苯并噻唑-2-基)乙酮
• 英文名称: 1-(6-methoxy-benzothiazol-2-yl)-ethanone
• 英文别名: 1-(6-methoxybenzo[d]thiazol-2-yl)ethanone；2-Acetyl-6-methoxybenzothiazol；1-(6-methoxy-1,3-benzothiazol-2-yl)ethanone
• CAS: 65840-58-6
• 化学式: C₁₀H₉NO₂S
• 分子量: 207.253
• InChiKey: LYFRQMFSTCKOIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  1-(6-甲氧基-1,3-苯并噻唑-2-基)乙酮 在 盐酸 、 盐酸羟胺 、 氢溴酸 、 铁粉 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 3-methyl-1-[(1R,5S)-3-oxabicyclo[3.1.0]hexan-1-yl]-6-(quinolin-2-ylmethoxy)imidazo[5,1-b][1,3]benzothiazole
  参考文献：
  名称：

  Discovery of benzo[d]imidazo[5,1-b]thiazole as a new class of phosphodiesterase 10A inhibitors

  摘要：

  The design, synthesis and structure activity relationship studies of a series of compounds from benzo[d]imidazo[5,1-b]thiazole scaffold as phosphodiesterase 10A (PDE10A) inhibitors are discussed. Several potent analogs with heteroaromatic substitutions (9a-d) were identified. The anticipated binding mode of these analogs was confirmed by performing the in silico docking experiments. Later, the heteroaromatics were substituted with saturated heteroalkyl groups which provided a tool compound 9e with excellent PDE10A activity, PDE selectivity, CNS penetrability and with favorable pharmacokinetic profile in rats. Furthermore, the compound 9e was shown to be efficacious in the MK-801 induced psychosis model and in the CAR model of psychosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.027
• 作为产物：
  描述：

  2-氨基-6-甲氧基苯并噻唑 在 对甲苯磺酸 、 potassium iodide 、 lithium diisopropyl amide 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 14.17h， 生成 1-(6-甲氧基-1,3-苯并噻唑-2-基)乙酮
  参考文献：
  名称：

  Discovery of benzo[d]imidazo[5,1-b]thiazole as a new class of phosphodiesterase 10A inhibitors

  摘要：

  The design, synthesis and structure activity relationship studies of a series of compounds from benzo[d]imidazo[5,1-b]thiazole scaffold as phosphodiesterase 10A (PDE10A) inhibitors are discussed. Several potent analogs with heteroaromatic substitutions (9a-d) were identified. The anticipated binding mode of these analogs was confirmed by performing the in silico docking experiments. Later, the heteroaromatics were substituted with saturated heteroalkyl groups which provided a tool compound 9e with excellent PDE10A activity, PDE selectivity, CNS penetrability and with favorable pharmacokinetic profile in rats. Furthermore, the compound 9e was shown to be efficacious in the MK-801 induced psychosis model and in the CAR model of psychosis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.027

文献信息

• Peroxides as “Switches” of Dialkyl <i>H</i>-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates
  作者：Xiao-Lan Chen、Xu Li、Ling-Bo Qu、Yu-Chun Tang、Wen-Peng Mai、Dong-Hui Wei、Wen-Zhu Bi、Li-Kun Duan、Kai Sun、Jian-Yu Chen、Dian-Dian Ke、Yu-Fen Zhao

  DOI：10.1021/jo501791n

  日期：2014.9.5

  Two mild and metal-free methods for the preparation of two kinds of important benzothiazole derivatives, 2-acylbenzothiazoles and dialkyl benzothiazol-2-ylphosphonates, respectively, were developed. The diallcyl H-phosphonate (RO)(2)P(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)(2)POH. TBHP triggered alpha-carbon-centered phosphite radical formation, whereas DTBP triggered phosphorus-centered phosphonate radical formation. The two types of radicals led respectively to two different reaction processes, the direct C-2-acylation of benzothiazoles and C-2-phosphonation of benzothiazoles.