2-氯-5,6-二甲氧基-苯并噻唑 | 864169-35-7

• 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: 2-氯-5,6-二甲氧基-苯并噻唑
• 英文名称: 2-chloro-5,6-dimethoxybenzo[d]thiazole
• 英文别名: 2-Chloro-5,6-dimethoxy-benzothiazole；2-chloro-5,6-dimethoxy-1,3-benzothiazole
• CAS: 864169-35-7
• 化学式: C₉H₈ClNO₂S
• 分子量: 229.687
• InChiKey: VQLUSLHALUKRLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯-5,6-二甲氧基-苯并噻唑 、 1-(3-氨基丙基)咪唑 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 24.0h， 以36.9%的产率得到N-(3-(1H-imidazol-1-yl)propyl)-5,6-dimethoxybenzo[d]thiazol-2-amine
  参考文献：
  名称：

  The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship

  摘要：

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.

  DOI：

  10.1021/jm050756e
• 作为产物：
  描述：

  5,6-二甲氧基-1,3-苯并噻唑-2-胺 在 copper dichloride 、 亚硝酸异戊酯 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 2-氯-5,6-二甲氧基-苯并噻唑
  参考文献：
  名称：

  In vitroandin silicodetermination of glutaminyl cyclase inhibitors

  摘要：

  合理设计新的hQC抑制剂。

  DOI：

  10.1039/c9ra05763c

文献信息

• Synthesis of APTRA Derivatives as Building Blocks for Low-Affinity Fluorescent Ca²⁺Indicators
  作者：Wim Dehaen、Bert Metten、Mario Smet、Noël Boens

  DOI：10.1055/s-2005-869900

  日期：——

  A new method for the synthesis of trialkyl aminophenoltriacetates (APTRA triesters) and the functionalization of these into suitable building blocks for potential fully conjugated low-affinity fluorescent Ca2+ indicators are described.

  本文介绍了一种合成三烷基氨基苯酚三乙酸酯（APTRA 三酯）的新方法，以及将这些三烷基氨基苯酚三乙酸酯官能化为潜在的全共轭低亲和性荧光 Ca2+ 指示剂的合适构件。
• <i>In vitro</i>and<i>in silico</i>determination of glutaminyl cyclase inhibitors
  作者：Phuong-Thao Tran、Van-Hai Hoang、Jeewoo Lee、Tran Thi Thu Hien、Nguyen Thanh Tung、Son Tung Ngo

  DOI：10.1039/c9ra05763c

  日期：——

  Rational design of new hQC inhibitors.

  合理设计新的hQC抑制剂。
• The First Potent Inhibitors for Human Glutaminyl Cyclase:  Synthesis and Structure−Activity Relationship
  作者：Mirko Buchholz、Ulrich Heiser、Stephan Schilling、André J. Niestroj、Katrin Zunkel、Hans-Ulrich Demuth

  DOI：10.1021/jm050756e

  日期：2006.1.1

  The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the molecules, which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC.