6-(benzyloxy)benzo[d]thiazole-2-carbonitrile | 676460-23-4

• 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: 6-(benzyloxy)benzo[d]thiazole-2-carbonitrile
• 英文别名: 6-benzyloxybenzothiazol-2-carbonitrile；6-(benzyloxy)-2-cyanobenzothiazole；6-Phenylmethoxy-1,3-benzothiazole-2-carbonitrile
• CAS: 676460-23-4
• 化学式: C₁₅H₁₀N₂OS
• 分子量: 266.323
• InChiKey: QDYYUEBEIUPGJB-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±37.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(benzyloxy)benzo[d]thiazole-2-carbonitrile 在 硫化氢 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到6-(benzyloxy)benzo[d]thiazole-2-carbothioamide
  参考文献：
  名称：

  From Liquid to Solid-State Fluorescence: Tricyclic Lactones Based on 4-Hydroxy-1,3-thiazoles

  摘要：

  This work describes the synthesis of a series of tricyclic lactones based on 4-hydroxy-1,3-thiazoles prepared by the classic Hantzsch synthesis. The tricyclic lactones are more rigid than the parent 4-hydroxythiazoles and are featured not only by fluorescence in solution, but also in the solid state. An extension of the chromophoric system was successfully realized by integration of the benzothiazole substructure, thus resulting in bathochromic shifts of absorption and also fluorescence. The new synthesized lactones additionally show interesting properties in solution, whereby the initial blue fluorescence changes dramatically with a variation of the pH value.

  DOI：

  10.1055/s-0033-1340048
• 作为产物：
  描述：

  2-(4-benzyloxyphenylamino)-2-thioxoacetamide 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 、 三氯氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-(benzyloxy)benzo[d]thiazole-2-carbonitrile
  参考文献：
  名称：

  A new application of the “mild thiolation” concept for an efficient three-step synthesis of 2-cyanobenzothiazoles: a new approach to Firefly-luciferin precursors

  摘要：

  An easy, low cost and upscalable three-step synthesis of Firefly luciferin precursors is presented. The 6-alkoxy-2-cyano-benzothiazoles (1) were synthesized starting from easily available O-alkylated 4-aminophenoles (2) via a mild thiolation, Jacobsen cyclization and dehydratization sequence.[GRAPHICS].

  DOI：

  10.1080/17415993.2011.641558

文献信息

• On the use of peroxy-caged luciferin (PCL-1) probe for bioluminescent detection of inflammatory oxidants in vitro and in vivo – Identification of reaction intermediates and oxidant-specific minor products
  作者：Jacek Zielonka、Radosław Podsiadły、Monika Zielonka、Micael Hardy、Balaraman Kalyanaraman

  DOI：10.1016/j.freeradbiomed.2016.07.023

  日期：2016.10

  first used to image hydrogen peroxide in living systems (Van de Bittner et al., 2010 [9]). Recently this probe was shown to react with peroxynitrite more potently than with hydrogen peroxide (Sieracki et al., 2013 [11]) and was suggested to be a more suitable probe for detecting peroxynitrite under in vivo conditions. In this work, we investigated in detail the products formed from the reaction between

  过氧笼式荧光素（PCL-1）探针首先用于在生物系统中对过氧化氢成像（Van de Bittner等人，2010 [9]）。最近，该探针与过氧亚硝酸盐的反应比与过氧化氢的反应更有效（Sieracki等，2013 [11]），被认为是在体内条件下检测过氧亚硝酸盐的更合适的探针。在这项工作中，我们详细研究了PCL-1与过氧化氢，次氯酸盐和过氧亚硝酸盐之间的反应形成的产物。HPLC分析表明，过氧化氢与PCL-1反应缓慢，形成萤光素是唯一的产物。次氯酸盐与PCL-1的次氯酸盐反应产生的萤光素明显减少，因为次氯酸盐将萤光素氧化成氯化的萤光素。PCL-1与过氧亚硝酸盐之间的反应由主要途径和次要途径组成。主要途径产生萤光素，次要途径产生自由基介导的硝化萤光素。自由基中间体的特征是自旋俘获。我们得出的结论是，除了在体内进行生物发光外，对氯化和硝化产物的监测还将有助于确定负责源自PCL-1的生物发光的氧化剂的性质。
• Luciferin Amides
  申请人：UNIVERSITY OF MASSACHUSETTS

  公开号：US20140193340A1

  公开（公告）日：2014-07-10

  This disclosure relates to luciferin amides of formula (I) shown below: Each variable in formula (I) is defined in the specification. These compounds can be used to detect fatty acid amide hydrolase activities in vitro, in live cells, or in vivo.

  这项披露涉及下面所示的式(I)的荧光素酰胺：式(I)中的每个变量在说明书中有定义。这些化合物可用于检测体外、活细胞或体内的脂肪酸酰胺水解酶活性。
• Luminescence-based methods and probes for measuring cytochrome P450 activity
  申请人：Promega Corporation

  公开号：US07692022B2

  公开（公告）日：2010-04-06

  The present invention provides methods, compositions, substrates, and kits useful for analyzing the metabolic activity in cells, tissue, and animals and for screening test compounds for their effect on cytochrome P450 activity. In particular, a one-step and two-step methods using luminogenic molecules, e.g. luciferin or coelenterazines, that are cytochrome P450 substrates and that are also bioluminescent enzyme, e.g., luciferase, pro-substrates are provided. Upon addition of the luciferin derivative or other luminogenic molecule into a P450 reaction, the P450 enzyme metabolizes the molecule into a bioluminescent enzyme substrate, e.g., luciferin and/or luciferin derivative metabolite, in a P450 reaction. The resulting metabolite(s) serves as a substrate of the bioluminescent enzyme, e.g., luciferase, in a second light-generating reaction. Luminescent cytochrome P450 assays with low background signals and high sensitivity are disclosed and isoform selectivity is demonstrated. The present invention also provides an improved method for performing luciferase reactions which employs added pyrophosphatase to remove inorganic pyrophosphate, a luciferase inhibitor which may be present in the reaction mixture as a contaminant or may be generated during the reaction. The present method further provides a method for stabilizing and prolonging the luminescent signal in a luciferase-based assay using luciferase stabilizing agents such as reversible luciferase inhibitors.

  本发明提供了用于分析细胞、组织和动物中代谢活性的方法、组合物、基质和试剂盒，以及用于筛选测试化合物对细胞色素P450活性影响的方法。具体来说，提供了使用发光分子（例如luciferin或coelenterazines）的一步和两步方法，这些分子是细胞色素P450的底物，同时也是生物发光酶（例如luciferase）的前体底物。将luciferin衍生物或其他发光分子加入到P450反应中后，P450酶将将该分子代谢成生物发光酶底物，例如luciferin和/或luciferin衍生物代谢物，在P450反应中。生成的代谢物作为生物发光酶（例如luciferase）的底物，在第二个生成光的反应中发挥作用。公开了低背景信号和高灵敏度的发光细胞色素P450测定方法，并展示了异构体选择性。本发明还提供了一种改进的进行luciferase反应的方法，该方法使用添加的焦磷酸酶来去除无机焦磷酸盐，这是一种可能存在于反应混合物中的luciferase抑制剂，或者在反应过程中生成的污染物。本方法还提供了一种使用可逆luciferase抑制剂等luciferase稳定剂来稳定和延长luciferase基础测定中的发光信号的方法。
• BIOLUMINESCENT ASSAYS USING CYANOBENZOTHIAZOLE COMPOUNDS
  申请人：Kelts Jessica

  公开号：US20110223625A1

  公开（公告）日：2011-09-15

  The invention provides methods that employ derivatives of 2-cyano-6-hydroxy- or 2-cyano-6-amino-benzothiazole, for example, in a bioluminogenic reaction. The invention further provides methods for detecting or determining the presence of molecules and/or enzymes, the modulator activity of such molecules, and/or the activity of such enzymes. The methods are adaptable to high-throughput format.

  该发明提供了使用2-氰基-6-羟基或2-氰基-6-氨基苯并噻唑的衍生物的方法，例如在生物发光反应中使用。该发明还提供了用于检测或确定分子和/或酶的存在，这些分子的调节活性和/或这些酶的活性的方法。这些方法可适应于高通量格式。
• LUMINESCENCE-BASED METHODS AND PROBES FOR MEASURING CYTOCHROME P450 ACTIVITY
  申请人：PROMEGA CORPORATION

  公开号：US20140380514A1

  公开（公告）日：2014-12-25

  The invention provides compounds, compositions, methods, substrates, and kits useful for analyzing the metabolic activity in cells, tissue, and animals and for screening test compounds for their effect on cytochrome P450 activity. In particular, a one-step and two-step methods using luminogenic molecules, e.g. luciferins or coelenterazines, that are cytochrome P450 substrates and that are also bioluminescent enzyme, e.g., luciferase, pro-substrates are provided. The present method further provides a method for stabilizing and prolonging the luminescent signal in a luciferase-based assay using luciferase stabilizing agents such as reversible luciferase inhibitors.

  本发明提供了化合物、组合物、方法、基质和工具，用于分析细胞、组织和动物中的代谢活性，并用于筛选测试化合物对细胞色素P450活性的影响。具体而言，提供了一步和两步方法，使用发光分子，例如荧光素或荧光素，它们是细胞色素P450底物，也是生物发光酶，例如荧光素酶，以及前体底物。本方法还提供了一种方法，使用可逆荧光素酶抑制剂等荧光素酶稳定剂稳定和延长荧光素酶基于荧光素的测定中的发光信号。