6-(tert-butyl)-2-chloro-10H-9-oxa-1-azaanthracen-10-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-(tert-butyl)-2-chloro-10H-9-oxa-1-azaanthracen-10-one
• 英文别名: 7-tert-butyl-2-chloro-1-azaxanthone；2-chloro-7-(1,1-dimethylethyl)-5H-[1]benzopyrano[2,3-b]pyridin-5-one；7-Tert-butyl-2-chlorochromeno[2,3-b]pyridin-5-one
• 化学式: C₁₆H₁₄ClNO₂
• 分子量: 287.746
• InChiKey: JQFFANOIGRTQMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(tert-butyl)-2-chloro-10H-9-oxa-1-azaanthracen-10-one 、 3-甲基吡唑 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以90%的产率得到6-(tert-butyl)-2-(3-methyl-1H-pyrazol-1-yl)-10H-9-oxa-1-azaanthracen-10-one
  参考文献：
  名称：

  Effective and efficient sensitisation of terbium luminescence at 355 nm with cell permeable pyrazoyl-1-azaxanthone macrocyclic complexes

  摘要：

  发射性铽配合物，适用于蛋白质共价结合，其包含吡唑啉基-1-氮杂咕吨染料发色团，已成功制备；它们展现细胞摄取能力，并具有较低的激发态淬灭敏感性。

  DOI：

  10.1039/b709805g
• 作为产物：
  描述：

  6-tert-butyl-1-methyl-1H-9-oxa-1-aza-anthracene-2,10-dione 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 反应 18.0h， 以49%的产率得到6-(tert-butyl)-2-chloro-10H-9-oxa-1-azaanthracen-10-one
  参考文献：
  名称：

  发射性和细胞渗透性的3-吡啶基和3-吡唑基-4-氮杂蒽酮镧系元素络合物及其在纤维素中的行为

  摘要：

  制备了一系列七个发射性euro（III）和b（III）配合物，在多齿大环配体中结合了3-吡啶基-4-氮杂蒽酮或3-吡唑基-4-氮杂蒽酮敏化部分。由于N，N'螯合的敏化剂的置换，在蛋白质或某些氧阴离子存在下，水性介质中较高的总发射量子产率会降低。然而，这些复合物被带入细胞并倾向于在线粒体的最初几个小时内定位，然后被运至内体区室。在存在竞争性抑制剂或定义明确的摄取途径的启动子的情况下，细胞摄取研究揭示了涉及巨胞饮作用的常见摄取机制。

  DOI：

  10.1002/hlca.200900122

文献信息

• Effective and efficient sensitisation of terbium luminescence at 355 nm with cell permeable pyrazoyl-1-azaxanthone macrocyclic complexes
  作者：Craig P. Montgomery、David Parker、Laurent Lamarque

  DOI：10.1039/b709805g

  日期：——

  Emissive terbium complexes, suitable for protein conjugation, incorporating a pyrazoyl-1-aza-xanthone chromophore have been prepared; they exhibit cellular uptake and possess a much lower sensitivity to excited state quenching.

  发射性铽配合物，适用于蛋白质共价结合，其包含吡唑啉基-1-氮杂咕吨染料发色团，已成功制备；它们展现细胞摄取能力，并具有较低的激发态淬灭敏感性。
• [EN] PYRIDYL-AZA(THIO)XANTHONE SENSITIZER COMPRISING LANTHANIDE(III) ION COMPLEXING COMPOUNDS, THEIR LUMINESCENT LANTHANIDE (III) ION COMPLEXES AND USE THEREOF AS FLUORESCENT LABELS.<br/>[FR] SENSIBILISATEUR PYRIDYL-AZA(THIO)XANTHONE COMPRENANT DES COMPOSÉS COMPLEXANT LES IONS LANTHANIDE(III), LEURS COMPLEXES DES IONS LANTHANIDE(III) LUMINESCENTS ET LEUR UTILISATION COMME MARQUEURS FLUORESCENTS
  申请人：CIS BIO INT

  公开号：WO2010084090A1

  公开（公告）日：2010-07-29

  Lanthanide (III) Ion completing compound comprising: (1) a sensitizer moiety of Formula (I) in which: a is an integer from 1 to 4; b is an integer equal to 1 or 2; c is an integer equal to 1 or 2; (R1)a, (R2)b, (R3)C are the same or different and are chosen from the group consisting of H; alkyl; -COOR4 where R4 is H or an alkyl; aryl; heteroaryl; saturated or unsaturated cyclic hydrocarbon; CF3; CN; a halogen atom; L-Rg; L-Sc; or two consecutive R3, two consecutive R2 or two consecutive R1 groups together form an aryl or a heteroaryl group or a saturated or unsaturated cyclic hydrocarbon group; where L is a linker, Rg is a reactive group and Sc is a conjugated substance; X1 and X2 are the same or different and are O or S; A is either a direct bond or a divalent group chosen from -CH2- or -(CH2)2-, said moiety being covalentiy attached to (2) a lanthanide (in) ion chelating moiety through A. The above compounds are used in the preparation of luminescent lanthanide (III) ion complexes which are used as fluorescent labels.

  镧系（III）离子配合物包括：（1）式（I）中的感光团，其中：a是1到4之间的整数；b是等于1或2的整数；c是等于1或2的整数；（R1）^a，（R2）^b，（R3）^c相同或不同，并选自H；烷基；-COOR4，其中R4为H或烷基；芳基；杂芳基；饱和或不饱和环烃；CF3；CN；卤原子；L-Rg；L-Sc；或两个连续的R3，两个连续的R2或两个连续的R1组成芳基或杂芳基或饱和或不饱和环烃基；其中L是连接物，Rg是反应性基团，Sc是共轭物质；X1和X2相同或不同，为O或S；A是直接键或从-CH2-或-(CH2)2-中选择的二价基团，所述团通过A与（2）中的镧系（III）离子螯合团结合。上述化合物用于制备发光的镧系（III）离子配合物，用作荧光标记剂。
• [EN] LANTHANIDE (III) ION COMPLEXING COMPOUNDS, LUMINESCENT LANTHANIDE (III) ION COMPLEXES AND USE THEREOF AS FLUORESCENT LABELS<br/>[FR] COMPOSÉS COMPLEXANT LES IONS LANTHANIDE (III), COMPLEXES LUMINESCENTS D'IONS LANTHANIDE (III) ET LEUR UTILISATION COMME MARQUEURS FLUORESCENTS
  申请人：CIS BIO INT

  公开号：WO2009010580A1

  公开（公告）日：2009-01-22

  Lanthanide (III) ion complexing compound comprising: (1) a sensitizer moiety of formula (I) in which: a is an integer from 1 to 4; b is an integer equal 1 or 2; c is an integer equal to 1 or 2; (R1)a, (R2)b, (R3)C are the same or different and are chosen from the group consisting of: H; alkyl; -COOR4 where R4 is H or an alkyl; aryl; heteroaryl; saturated or unsaturated cyclic hydrocarbon; CF3; CN; a halogen atom; L-Rg; L-Sc; or two consecutive R3, two consecutive R2 or two consecutive R1 groups together form an aryl or a heteroaryl group or a saturated or unsaturated cyclic hydrocarbon group; where L is a linker, Rg is a reactive group and Sc is a conjugated substance; X1 and X2 are the same or different and are O or S; A is either a direct bond or a divalent group chosen from -CH2- or -(CH2)2-, said moiety being covalently attached to (2) a lanthanide (III) ion chelating moiety through A. Application: Preparation of luminescent lanthanide (III) ion complexes and use thereof as fluorescent labels.

  镧系（III）离子络合物，包括：（1）具有以下式（I）的感光基团，其中：a是1到4之间的整数；b是等于1或2的整数；c是等于1或2的整数；（R1）^a，（R2）^b，（R3）^c相同或不同，并选自以下群体：H；烷基；-COOR4，其中R4为H或烷基；芳基；杂环芳基；饱和或不饱和环烃；CF3；CN；卤原子；L-Rg；L-Sc；或两个连续的R3，两个连续的R2或两个连续的R1基团共同形成芳基或杂环芳基或饱和或不饱和环烃基团；其中L是连接物，Rg是反应性基团，Sc是共轭物质；X1和X2相同或不同，为O或S；A是直接键或从-CH2-或-(CH2)2-中选择的二价基团，所述基团通过A与（2）具有配位基团的镧系（III）离子共价连接。应用：制备发光的镧系（III）离子络合物并将其用作荧光标记剂。
• LANTHANIDE (III) ION COMPLEXING COMPOUNDS, LUMINESCENT LANTHANIDE (III) ION COMPLEXES AND USE THEREOF AS FLUORESCENT LABELS
  申请人：Lamarque Laurent

  公开号：US20100204467A1

  公开（公告）日：2010-08-12

  Lanthanide (III) ion complexing compound comprising: (1) a sensitizer moiety of formula (I) in which: a is an integer from 1 to 4; b is an integer equal 1 or 2; c is an integer equal to 1 or 2; (R 1 )a, (R 2 )b, (R 3 )c are the same or different and are chosen from the group consisting of: H; alkyl; —COOR 4 where R 4 is H or an alkyl; aryl; heteroaryl; saturated or unsaturated cyclic hydrocarbon; CF 3 ; CN; a halogen atom; L-Rg; L-Sc; or two consecutive R 3 , two consecutive R 2 or two consecutive R 1 groups together form an aryl or a heteroaryl group or a saturated or unsaturated cyclic hydrocarbon group; where L is a linker, Rg is a reactive group and Sc is a conjugated substance; X 1 and X 2 are the same or different and are O or S; A is either a direct bond or a divalent group chosen from —CH 2 — or —(CH 2 ) 2 —, said moiety being covalently attached to (2) a lanthanide (III) ion chelating moiety through A. Application: Preparation of luminescent lanthanide (III) ion complexes and use thereof as fluorescent labels.

  镧系元素（III）离子络合物包括：（1）式（I）的敏化剂基团，其中：a是1至4的整数；b是1或2的整数；c是1或2的整数；（R1）a，（R2）b，（R3）c相同或不同，选择自H；烷基；-COOR4，其中R4为H或烷基；芳基；杂芳基；饱和或不饱和的环烃；CF3；CN；卤素原子；L-Rg；L-Sc；或两个连续的R3，两个连续的R2或两个连续的R1组成芳基或杂芳基或饱和或不饱和的环烃基团；其中L是一个连接剂，Rg是一个反应性基团，Sc是一个共轭物质；X1和X2相同或不同，为O或S；A是直接键或选择自-CH2-或-（CH2）2-的二价基团，该基团与（2）镧系元素（III）离子螯合基团通过A共价连接。应用：制备发光的镧系元素（III）离子络合物，并将其用作荧光标记。
• Emissive and Cell-Permeable 3-Pyridyl- and 3-Pyrazolyl-4-azaxanthone Lanthanide Complexes and Their Behaviour<i>in cellulo</i>
  作者：Craig P. Montgomery、Elizabeth J. New、Lars O. Palsson、David Parker、Andrei S. Batsanov、Laurent Lamarque

  DOI：10.1002/hlca.200900122

  日期：2009.11

  seven emissive europium(III) and terbium(III) complexes was prepared, incorporating a 3‐pyridyl‐4‐azaxanthone or 3‐pyrazolyl‐4‐azaxanthone sensitising moiety within a polydentate macrocyclic ligand. High overall emission quantum yields in aqueous media are attenuated in the presence of protein or certain oxy anions due to displacement of the N,N′‐chelated sensitiser. Nevertheless, these complexes are

  制备了一系列七个发射性euro（III）和b（III）配合物，在多齿大环配体中结合了3-吡啶基-4-氮杂蒽酮或3-吡唑基-4-氮杂蒽酮敏化部分。由于N，N'螯合的敏化剂的置换，在蛋白质或某些氧阴离子存在下，水性介质中较高的总发射量子产率会降低。然而，这些复合物被带入细胞并倾向于在线粒体的最初几个小时内定位，然后被运至内体区室。在存在竞争性抑制剂或定义明确的摄取途径的启动子的情况下，细胞摄取研究揭示了涉及巨胞饮作用的常见摄取机制。