6-benzyl-3-(4-hydroxyphenyl)thiazolo[3,2-b]-1,2,4-triazin-7-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-benzyl-3-(4-hydroxyphenyl)thiazolo[3,2-b]-1,2,4-triazin-7-one
• 英文别名: 6-benzyl-3-(4-hydroxyphenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one；6-Benzyl-3-(4-hydroxyphenyl)-[1,3]thiazolo[3,2-b][1,2,4]triazin-7-one；6-benzyl-3-(4-hydroxyphenyl)-[1,3]thiazolo[3,2-b][1,2,4]triazin-7-one
• 化学式: C₁₈H₁₃N₃O₂S
• 分子量: 335.386
• InChiKey: LNXRJLZZJPDEMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.49
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-benzyl-3-(4-hydroxyphenyl)thiazolo[3,2-b]-1,2,4-triazin-7-one 、 N,N-二乙基氯乙胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以75.6%的产率得到6-benzyl-3-(4-[(2-diethylamino)ethoxy]phenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 7H-Thiazolo[3,2-b]-1,2,4-triazin-7-one Derivatives as Dual Binding Site Acetylcholinesterase Inhibitors

  摘要：

  A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were designed, synthesized and evaluated as dual binding site acetylcholinesterase inhibitors. The target compounds exhibited promising inhibitory activity for AChE. The structure-activity relationships were discussed and their binding conformation and simultaneous interactions mode were further clarified by the molecular docking studies.

  DOI：

  10.3987/com-18-12820
• 作为产物：
  描述：

  苯丙酮酸 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 6-benzyl-3-(4-hydroxyphenyl)thiazolo[3,2-b]-1,2,4-triazin-7-one
  参考文献：
  名称：

  7H-噻唑并[3,2-b] -1,2,4-三嗪-7-one衍生物的合成，β-catenin转运能力和ALP活化活性。

  摘要：

  背景技术骨质疏松症（OP）是一种常见的骨病，最常在绝经后的女性中诊断出来。大多数OP治疗都集中在对患者激素水平的控制上，因此，它们与严重的不良反应有关。目的研究，合成和评估7H-噻唑并[3,2-b] -1,2,4-三嗪-7-one衍生物的β-连环蛋白转运能力和碱性磷酸酶（ALP）活化活性。方法以苯乙烯衍生物为原料，经氧化和缩合反应，得到6-芳基-3-硫代-3,4-二氢-1,2,4-三嗪-5（2H）-一衍生物（1 ）。通过化合物1与取代的苯甲酰氯在乙酸中的缩合反应获得3,6-二芳基-7H-噻唑并[3,2-b] -1,2,4-三嗪-7-（2）。通过化合物2与取代的烷基氯经威廉姆森反应制备目标化合物3,6-二芳基-7H-噻唑并[3,2-b] -1,2,4-三嗪-7-（3a-3c）。以6-苄基-3-芳基-7H-噻唑并[3,2-b] -1,2,4-三嗪-7-一衍生物为目标化合物，以苯甲醛和乙酰基甘氨

  DOI：

  10.2174/1573406413666171002121443

文献信息

• 噻唑并[3,2-b]-1,2,4-三嗪衍生物及其应用
  申请人：沈阳药科大学

  公开号：CN105949220B

  公开（公告）日：2018-05-25

  本发明属于医药技术领域，涉及噻唑并[3,2‑b]‑1,2,4‑三嗪类衍生物及其应用。噻唑并[3,2‑b]‑1,2,4‑三嗪类衍生物包括噻唑并[3,2‑b]‑1,2,4‑三嗪类衍生物、该类化合物的立体异构体和药学上适用的盐，其结构通式如下所示：噻唑并[3,2‑b]‑1,2,4‑三嗪类衍生物以及该类化合物药学上适用的酸加成的盐，可以与现有药物合并或单独使用作为葡萄糖浓度依赖型胰岛素分泌促进剂，用于II型糖尿病的治疗。与现有技术相比，该类化合物是葡萄糖浓度依赖型胰岛素分泌促进剂，可在高葡萄糖浓度下促进胰岛素分泌，而在低葡萄糖浓度下，不影响胰岛素的分泌，从而避免了低血糖副作用的发生。
• Synthesis and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as dual binding site acetylcholinesterase inhibitors
  作者：Sijie Liu、Ruofeng Shang、Lanxiang Shi、David Chi-Cheong Wan、Huangquan Lin

  DOI：10.1016/j.ejmech.2014.05.020

  日期：2014.6

  A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives 7a-i were synthesized and evaluated as novel acetylcholinesterase (AChE) inhibitors. All target compounds were evaluated in vitro for the inhibitory activities against AChE via Ellman colorimetric assay. Compound 7c showed an excellent (89.82%) inhibitory activity. The molecular docking studies revealed that 7c, 7d and 7g, with the lateral chain in the para position of the phenyl ring, possessed an optimal docking pose and can perfectly fit into the catalytic active site (CAS) and peripheral anionic site (PAS), simultaneously, and, consequently, exhibited higher inhibitory potency than 7b that bears the same lateral chain as 7g, but in the ortho position of the phenyl ring. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis, β -catenin Translocation Capability and ALP Activation Activity of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one Derivatives
  作者：Shicheng Hou、Henan Xu、Jianshu Hu、Jian Hou、Yan Wang、Zhe Jin、David C.C. Wan、Chun Hu

  DOI：10.2174/1573406413666171002121443

  日期：2018.1.11

  derivatives were synthesized as raw materials, followed by oxidation and condensation reactions, in which 6-aryl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one derivatives (1) were obtained. The 3,6-diaryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-ones (2) were obtained by a condensation reaction of compound 1 with substituted phenacyl chlorides in acetic acid. The target compounds 3,6-diaryl-7H-thiazolo[3,2-b]-1

  背景技术骨质疏松症（OP）是一种常见的骨病，最常在绝经后的女性中诊断出来。大多数OP治疗都集中在对患者激素水平的控制上，因此，它们与严重的不良反应有关。目的研究，合成和评估7H-噻唑并[3,2-b] -1,2,4-三嗪-7-one衍生物的β-连环蛋白转运能力和碱性磷酸酶（ALP）活化活性。方法以苯乙烯衍生物为原料，经氧化和缩合反应，得到6-芳基-3-硫代-3,4-二氢-1,2,4-三嗪-5（2H）-一衍生物（1 ）。通过化合物1与取代的苯甲酰氯在乙酸中的缩合反应获得3,6-二芳基-7H-噻唑并[3,2-b] -1,2,4-三嗪-7-（2）。通过化合物2与取代的烷基氯经威廉姆森反应制备目标化合物3,6-二芳基-7H-噻唑并[3,2-b] -1,2,4-三嗪-7-（3a-3c）。以6-苄基-3-芳基-7H-噻唑并[3,2-b] -1,2,4-三嗪-7-一衍生物为目标化合物，以苯甲醛和乙酰基甘氨
• Design, Synthesis, and Biological Evaluation of 7H-Thiazolo[3,2-b]-1,2,4-triazin-7-one Derivatives as Dual Binding Site Acetylcholinesterase Inhibitors
  作者：Chun Hu、Si-Jie Liu、Li-Bo Cui、Hiu-Lan Xu、Tie-Ying Wang、Shuo Li、Huang-Quan Lin、Daivd Chicheong Wan

  DOI：10.3987/com-18-12820

  日期：——

  A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were designed, synthesized and evaluated as dual binding site acetylcholinesterase inhibitors. The target compounds exhibited promising inhibitory activity for AChE. The structure-activity relationships were discussed and their binding conformation and simultaneous interactions mode were further clarified by the molecular docking studies.