5-羟基苯并[d]噻唑-2-甲腈 | 7267-38-1

• 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: 5-羟基苯并[d]噻唑-2-甲腈
• 中文别名: 5-羟基-2-氰基苯并噻唑
• 英文名称: 5-hydroxybenzo[d]thiazole-2-carbonitrile
• 英文别名: 5-hydroxy-benzothiazole-2-carbonitrile；5-Hydroxy-benzothiazol-2-carbonitril；5-hydroxy-1,3-benzothiazole-2-carbonitrile
• CAS: 7267-38-1
• 化学式: C₈H₄N₂OS
• 分子量: 176.199
• InChiKey: DTXINWSDUBHXMK-UHFFFAOYSA-N

物化性质

• 熔点：
  193.5-194.0 °C
• 沸点：
  374.7±34.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934200090
• 储存条件：
  存储于惰性气体保护下，并在室温条件下保存。

反应信息

• 作为反应物：
  描述：

  DL-半胱氨酸 、 5-羟基苯并[d]噻唑-2-甲腈 以 甲醇 、 水 为溶剂， 生成 2-(5-hydroxy-benzothiazol-2-yl)-4,5-dihydro-thiazole-4-carboxylic acid
  参考文献：
  名称：

  萤火虫萤光素的类似物。3。

  摘要：

  DOI：

  10.1021/jo01343a039
• 作为产物：
  描述：

  5-甲氧基-苯并噻唑-2-羧酸酰胺 在 吡啶盐酸盐 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 生成 5-羟基苯并[d]噻唑-2-甲腈
  参考文献：
  名称：

  萤火虫萤光素的类似物。3。

  摘要：

  DOI：

  10.1021/jo01343a039

文献信息

• Novel Heterocyclic Analogues of Firefly Luciferin
  作者：Carolyn C. Woodroofe、Poncho L. Meisenheimer、Dieter H. Klaubert、Yumi Kovic、Justin C. Rosenberg、Curran E. Behney、Tara L. Southworth、Bruce R. Branchini

  DOI：10.1021/bi301411d

  日期：2012.12.11

  Five novel firefly luciferin analogues in which the benzothiazole ring system of the natural substrate was replaced with benzimidazole, benzofuran, benzothiophene, benzoxazole, and indole were synthesized. The fluorescence, bioluminescence, and kinetic properties of the compounds were evaluated with recombinant Photinus pyralis wild type luciferase. With the exception of indole, all of the substrates

  合成了五个新颖的萤火虫荧光素类似物，其中天然底物的苯​​并噻唑环系统被苯并咪唑，苯并呋喃，苯并噻吩，苯并恶唑和吲哚代替。用重组Photinus pyralis评估化合物的荧光，生物发光和动力学性质野生型荧光素酶。除吲哚外，所有含有杂环取代基的底物均使用荧光素酶产生易于测量的闪光。与萤光素相比，在具有最佳pH和达到最大强度的时间不同的反应中，强度范围为0.3％至4.4％。杂原子的变化影响了荧光和生物发光发射光谱，分别显示了479-528和518-574 nm的最大值。虽然这组结构相似的底物类似物在光谱和生物发光特性方面存在一些有趣的趋势，但最重要的发现与含苯并噻吩的化合物有关。这种合成的底物产生缓慢的衰变辉光动力学，使荧光素酶的总基于光的比活性相对于荧光素值增加了4倍以上。此外，在6.2-9.4的pH范围内，最大发射为523 nm，与天然底物相比，蓝移异常37纳米。苯并噻吩荧光素的非凡的生物
• [EN] PCL COMPOUNDS, COMPOSITIONS, AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS PCL, COMPOSITIONS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV ILLINOIS

  公开号：WO2014127360A1

  公开（公告）日：2014-08-21

  Disclosed herein are compounds useful for detecting oxidants in a living cell, in a multicellular organism, or in a cell-free sample. In particular, disclosed herein are bioluminescent reporter compounds, and more particularly, fluorinated peroxy-caged- luciferin (PCL) compounds, compositions comprising such compounds, methods of using such compounds and compositions, and processes for preparing such compounds. Also disclosed herein are kits and methods for detecting and measuring peroxynitrite, and optionally, additional oxidants in a living cell, in a multicellular organism, or in a cell-free sample.

  本文披露了一些化合物，用于在活细胞、多细胞生物或无细胞样品中检测氧化剂。具体而言，本文披露了生物发光报告化合物，尤其是氟代过氧化物-包埋-路西非因（PCL）化合物，包括这种化合物的组合物，使用这种化合物和组合物的方法以及制备这种化合物的过程。本文还披露了用于检测和测量过硝酸盐和可选的其他氧化剂在活细胞、多细胞生物或无细胞样品中的试剂盒和方法。
• Synthesis of Fused 1,2,4-Dithiazines and 1,2,3,5-Trithiazepines
  作者：Maria Koyioni、Maria Manoli、Panayiotis A. Koutentis

  DOI：10.1021/jo501881y

  日期：2014.10.17

  Reacting (Z)-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1H-pyrazol-5-amines 5 with Et2NH and then with concd H2SO4 gives 5H-pyrazolo[3,4-e][1,2,4]dithiazine-3-carbonitriles 7 in good yields (74-85%) and 6H-pyrazolo[3,4-f][1,2,3,5]trithiazepine-4-carbonitriles 9 as minor products (0-6%). Furthermore, the 1,3-dimethylpyrazole analogue 5a was transformed into the dithiazine 7a in two discrete steps, allowing the isolation of a disulfide intermediate (Z)-2-[(diethylamino)disulfan-yl]-2-[(1H-pyrazol-5-yl)imino]acetonitrile (8a). The one-pot, two-step reaction also worked with electron-rich hydroxy- and methoxy-substituted anilines. Thermolysis of the pyrazolo[3,4-e][1,2,4]dithiazines 7 gave the ring-contracted 1H-pyrazolo[3,4-d]thiazole-5-carbonitriles 6 (94-100%). With active sulfur, 1,3-dimethyl-5H-pyrazolo[3,4-e][1,2,4]dithiazine-3-carbonitrile (7a) gave 1,3-dimethyl-6H-pyrazolo[3,4-f][1,2,3,5]trithiazepine-4-carbonitrile (9a), but on prolonged reaction times, it gave 5,7-dimethyl-5H-[1,2,3]dithiazolo[4,5-b]pyrazolo[3,4-e][1,4]thiazine (13). Finally, in the absence of acid, heating a solution of (Z)-2-[(diethylamino)disulfanyl]-2-[(1,3-dimethyl-1H-pyrazol-5-yl)imino]acetonitrile (8a) gave 4,6,10,12-tetramethyl-6H-pyrazolo[3,4-f]pyrazolo[3',4':4,5]pyrimido[6,1-d][1,2,3,5]trithiazepine-8,12b(10H)-dicarbonitrile (19) (67%).
• ACTIVATORS FOR TWO PART CYANOACRYLATE ADHESIVES
  申请人：Henkel IP & Holding GmbH

  公开号：EP2346956B1

  公开（公告）日：2017-12-06
• PCL Compounds, Compositions, And Methods Of Use Thereof
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US20150376680A1

  公开（公告）日：2015-12-31

  Disclosed herein are compounds useful for detecting oxidants in a living cell, in a multicellular organism, or in a cell-free sample. In particular, disclosed herein are bioluminescent reporter compounds, and more particularly, fluorinated peroxy-caged-luciferin (PCL) compounds, compositions comprising such compounds, methods of using such compounds and compositions, and processes for preparing such compounds. Also disclosed herein are kits and methods for detecting and measuring peroxynitrite, and optionally, additional oxidants in a living cell, in a multicellular organism, or in a cell-free sample.