2-(6-hydroxy-benzothiazol-2-yl)-thiazole-4-carboxylic acid ethyl ester | 36727-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(6-hydroxy-benzothiazol-2-yl)-thiazole-4-carboxylic acid ethyl ester
• 英文别名: dehydroluciferin ethyl ester；Dehydroluciferin-ethylester；Ethyl 2-(6-hydroxy-1,3-benzothiazol-2-yl)-1,3-thiazole-4-carboxylate
• CAS: 36727-09-0
• 化学式: C₁₃H₁₀N₂O₃S₂
• 分子量: 306.366
• InChiKey: VCRZVFWWNMFURJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(6-hydroxy-benzothiazol-2-yl)-thiazole-4-carboxylic acid ethyl ester 在 lithium hydroxide 、 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 {2-[6-(2-methoxy-ethoxymethoxy)-benzothiazol-2-yl]-thiazole-4-carbonyl}-sulfamic acid 6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  Synthesis of an N-acyl sulfamate analog of luciferyl-AMP: A stable and potent inhibitor of firefly luciferase

  摘要：

  In the first of two half-reactions resulting in the emission of visible light, firefly luciferase forms luciferyl-adenylate from its natural substrates beetle luciferin and Mg-ATP. The acyl-adenylate is subsequently oxidized producing the light emitter oxyluciferin in an electronically excited state. In vitro, under mild conditions of temperature and pH, the acyl-adenylate intermediate is readily hydrolyzed and susceptible to oxidation. We report here the multi-step synthesis and physical and enzymatic characterization of an N-acyl sulfamate analog of luciferyi-adenylate, 5'-O-[(N-dehydroluciferyl)-sulfamoyl]-adenosine (compound 5). This represents the first example of a stable and potent (K-i = 340 nM) reversible inhibitor of firefly luciferase activity based on the structure of the natural acyl-adenylate intermediate. Additionally, we present the results of limited proteolysis studies that demonstrate that the binding of the novel acyl-adenylate analog protects luciferase from proteolysis. The findings presented here are interpreted in the context of the hypothesis that luciferase and the other enzymes in a large superfamily of adenylate-forming proteins adopt two conformations to catalyze two different partial reactions. We anticipate that the novel N-acyl sulfamate analog will be a valuable reagent in future studies designed to elucidate the role of conformational changes in firefly luciferase catalyzed bioluminescence. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.115
• 作为产物：
  描述：

  ethyl 2-(6'-[tert-butyl(dimethyl)silyl]oxy-2'-benzothiazolyl)-thiazole-4-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 2-(6-hydroxy-benzothiazol-2-yl)-thiazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  由1,4-苯醌合成脱氢荧光素[2-（6'-羟基-2'-苯并噻唑基）-噻唑-4-羧酸]的新方法

  摘要：

  萤光素的氧化产物脱氢萤光素[2-（6'-羟基-2'-苯并噻唑基）-噻唑-4-羧酸]的新合成是从1,4-苯醌开始的。该化合物与1-半胱氨酸乙酯反应，然后进行氧化-环化步骤，得到2-羧乙氧基-6-羟基苯并噻唑，将其原位水解并脱羧成6-羟基苯并噻唑。对该关键中间体的叔丁基（二甲基）甲硅烷基醚进行α-锂化，然后用DMF进行甲酰化，并将所得醛与1-半胱氨酸乙酯缩合。中间体噻唑烷脱氢，然后脱保护，得到脱氢萤光素，其从1,4-苯醌的总产率为35％（从6-羟基苯并噻唑的产率为69％）。

  DOI：

  10.1016/j.tet.2013.05.019