(S)-4,5-二氢-2-(6-羟基-2-喹啉基)-4-噻唑羧酸 | 122364-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: (S)-4,5-二氢-2-(6-羟基-2-喹啉基)-4-噻唑羧酸
• 英文名称: (S)-2-(6-hydroxyquinolin-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
• 英文别名: quinolylluciferin；QLUC；2-(6-Hydroxyquinolyl)-2-thiazole-4-carboxylic acid；(4S)-2-(6-hydroxyquinolin-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• CAS: 122364-83-4
• 化学式: C₁₃H₁₀N₂O₃S
• 分子量: 274.3
• InChiKey: YLOLPLXXFZFHFD-LLVKDONJSA-N

物化性质

• 沸点：
  594.6±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-甲氧基-喹啉-2-甲腈 在 吡啶盐酸盐 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 3.5h， 生成 (S)-4,5-二氢-2-(6-羟基-2-喹啉基)-4-噻唑羧酸
  参考文献：
  名称：

  Luciferin and derivatives as a DYRK selective scaffold for the design of protein kinase inhibitors

  摘要：

  D-Luciferin is widely used as a substrate in luciferase catalysed bioluminescence assays for in vitro studies. However, little is known about cross reactivity and potential interference of D-luciferin with other enzymes. We serendipitously found that firefly luciferin inhibited the CDK2/Cyclin A protein kinase. Inhibition profiling of D-luciferin over a 103-protein kinase panel showed significant inhibition of a small set of protein kinases, in particular the DYRK-family, but also other members of the CMGC-group, including ERK8 and CK2. Inhibition profiling on a 16-member focused library derived from D-luciferin confirms that D-luciferin represents a DYRK-selective chemotype of fragment-like molecular weight. Thus, observation of its inhibitory activity and the initial SAR information reported here promise to be useful for further design of protein kinase inhibitors with related scaffolds. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.035

文献信息

• Luminogenic and fluorogenic compounds and methods to detect molecules or conditions
  申请人：Cali J. James

  公开号：US20070015790A1

  公开（公告）日：2007-01-18

  A method to detect the presence or amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided.

  提供了一种检测样品中至少一种分子存在或数量的方法，该方法采用了荧光素衍生物或荧光染料衍生物的衍生物。
• LUMINOGENIC AND FLUOROGENIC COMPOUNDS AND METHODS TO DETECT MOLECULES OR CONDITIONS
  申请人：Promega Corporation

  公开号：US20140154716A1

  公开（公告）日：2014-06-05

  A method to detect the presence or amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided. Compounds and compositions for carrying out the methods of the invention are also provided.

  本发明提供了一种检测样本中至少一种分子存在或数量的方法，该方法采用了luciferin的衍生物或荧光团的衍生物。还提供了用于执行本发明方法的化合物和组合物。
• Sensitive luciferin derived probes for selective carboxypeptidase activity
  作者：Yu-Cheng Chang、Pei-Wen Chao、Ching-Hsuan Tung

  DOI：10.1016/j.bmcl.2011.05.023

  日期：2011.7

  Highly selective luminescent probes, QLUC-TYR and LUC-GLU, for detection of carboxypeptidase activity were synthesized. Caged substrates were first cleaved by corresponding carboxypeptidases, and then they were activated by luciferase to emit light. Enzymatic activities of biologically important carboxypeptidases can be determined using this technology. (C) 2011 Elsevier Ltd. All rights reserved.
• BRANCHINI, BRUCE R.;HAYWARD, MATTHEW M.;BAMFORD, SARAH;BRENNAN, PATRICIA +, PHOTOCHEM. AND PHOTOBIOL., 49,(1989) N, C. 689-695
  作者：BRANCHINI, BRUCE R.、HAYWARD, MATTHEW M.、BAMFORD, SARAH、BRENNAN, PATRICIA +

  DOI：——

  日期：——
• US7951550B2
  申请人：——

  公开号：US7951550B2

  公开（公告）日：2011-05-31