2-(p-tolyl)-5,6-dihydrobenzo[d]thiazol-7(4H)-one | 1251924-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(p-tolyl)-5,6-dihydrobenzo[d]thiazol-7(4H)-one
• 英文别名: 2-(4-Methylphenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one；2-(4-methylphenyl)-5,6-dihydro-4H-1,3-benzothiazol-7-one
• CAS: 1251924-63-6
• 化学式: C₁₄H₁₃NOS
• mdl: MFCD16817558
• 分子量: 243.329
• InChiKey: DOIKXGZAVXQATN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(p-tolyl)-5,6-dihydrobenzo[d]thiazol-7(4H)-one 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到2-(4-Methylphenyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-7-ol
  参考文献：
  名称：

  3-Substituted 3-(4-aryloxyaryl)-propanoic acids as GPR40 agonists

  摘要：

  The design, synthesis, and structure-activity relationship (SAR) for a series of beta-substituted 3-(4-aryloxyaryl) propanoic acid GPR40 agonists is described. Systematic replacement of the pendant aryloxy group led to identification of potent GPR40 agonists. In order to identify candidates suitable for in vivo validation of the target, serum shifted potency and pharmacokinetic properties were determined for several compounds. Finally, further profiling of compound 7 is presented, including demonstration of enhanced glucose tolerance in an in vivo mouse model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.114
• 作为产物：
  描述：

  2-氨基-5,6-二氢-4H-苯并噻唑-7-酮 在 四(三苯基膦)钯 、 磷酸 、 硝酸 、 sodium carbonate 、 copper(I) bromide 、 sodium nitrite 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 生成 2-(p-tolyl)-5,6-dihydrobenzo[d]thiazol-7(4H)-one
  参考文献：
  名称：

  3-Substituted 3-(4-aryloxyaryl)-propanoic acids as GPR40 agonists

  摘要：

  The design, synthesis, and structure-activity relationship (SAR) for a series of beta-substituted 3-(4-aryloxyaryl) propanoic acid GPR40 agonists is described. Systematic replacement of the pendant aryloxy group led to identification of potent GPR40 agonists. In order to identify candidates suitable for in vivo validation of the target, serum shifted potency and pharmacokinetic properties were determined for several compounds. Finally, further profiling of compound 7 is presented, including demonstration of enhanced glucose tolerance in an in vivo mouse model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.114

文献信息

• Versatile approaches to a library of building blocks based on 5-acylthiazole skeleton
  作者：Olesia G. Kulyk、Dmytro A. Biloborodov、Maksim A. Cherevatenko、Yevhen Y. Shyriakin、Alexander Yu. Lyapunov、Alexander V. Mazepa、Valerii V. Vashchenko、Valeriy D. Orlov、Maksim A. Kolosov

  DOI：10.1080/00397911.2020.1808224

  日期：2020.12.1

  Abstract Thiazole derivatives represent an important class of azole heterocycles with a broad spectrum of biological activity and, therefore, the synthesis of these compounds is of remarkable concern. We present here practical and reliable protocol for synthesis of some 5-acylthiazoles and demonstrate their utility in the preparation of several new series of thiazole-containing building blocks through

  摘要 噻唑衍生物是一类重要的唑类杂环，具有广泛的生物活性，因此，这些化合物的合成备受关注。我们在此介绍了一些实用且可靠的合成一些 5-酰基噻唑的方案，并展示了它们在通过 5-酰基功能的转化制备几个新系列的含噻唑结构单元中的效用。具体而言，噻唑基醇、肟、伯胺和仲胺以良好到极好的收率连续合成。所得化合物的化学结构经 1H 和 13C NMR 光谱、元素分析和质谱证实。图形概要
• 3-Substituted 3-(4-aryloxyaryl)-propanoic acids as GPR40 agonists
  作者：Shawn P. Walsh、Alexandra Severino、Changyou Zhou、Jiafang He、Gui-Bai Liang、Carina P. Tan、Jin Cao、George J. Eiermann、Ling Xu、Gino Salituro、Andrew D. Howard、Sander G. Mills、Lihu Yang

  DOI：10.1016/j.bmcl.2011.03.114

  日期：2011.6

  The design, synthesis, and structure-activity relationship (SAR) for a series of beta-substituted 3-(4-aryloxyaryl) propanoic acid GPR40 agonists is described. Systematic replacement of the pendant aryloxy group led to identification of potent GPR40 agonists. In order to identify candidates suitable for in vivo validation of the target, serum shifted potency and pharmacokinetic properties were determined for several compounds. Finally, further profiling of compound 7 is presented, including demonstration of enhanced glucose tolerance in an in vivo mouse model. (C) 2011 Elsevier Ltd. All rights reserved.