3H-Indolium, 1-ethyl-5-methoxy-2,3,3-trimethyl-, iodide | 41626-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3H-Indolium, 1-ethyl-5-methoxy-2,3,3-trimethyl-, iodide
• 英文别名: 1-ethyl-5-methoxy-2,3,3-trimethylindol-1-ium;iodide
• CAS: 41626-12-4
• 化学式: C₁₄H₂₀NO*I
• 分子量: 345.223
• InChiKey: NJGSRFQZESCHAA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(3-(anilinomethylene)-2-chloro-1-cyclohexen-1-yl)methylene]aniline 、 3H-Indolium, 1-ethyl-5-methoxy-2,3,3-trimethyl-, iodide 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以54%的产率得到2-((E)-2-((E)-2-chloro-3-((E)-2-(1-ethyl-5-methoxy-3,3-dimethylindolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-1-ethyl-5-methoxy-3,3-dimethyl-3H-indol-1-ium iodide
  参考文献：
  名称：

  [EN] CANCER CELL INHIBITORY DRUG AND CANCER STEM-CELL DETECTION PROBE
  [FR] MÉDICAMENT INHIBITEUR DE CELLULES CANCÉREUSES ET SONDE DE DÉTECTION DE CELLULES SOUCHES CANCÉREUSES

  摘要：

  本发明的目的是提供一种癌细胞抑制药物，特别是一种癌干细胞抑制药物，或一种癌干细胞检测探针。本发明提供了一种包含至少一种以通式（1）表示的化合物作为活性成分的癌细胞抑制药物。

  公开号：

  WO2014065439A1
• 作为产物：
  描述：

  4-甲氧基苯肼盐酸盐 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 生成 3H-Indolium, 1-ethyl-5-methoxy-2,3,3-trimethyl-, iodide
  参考文献：
  名称：

  含苯并[c，d]吲哚的单次甲基花菁染料：合成和光物理性质。

  摘要：

  不对称的单次甲基花菁已广泛用作其他生物系统中核酸的探针。本文中，我们报告了七种单次甲基花青染料的合成，这些染料已成功制备成各种杂环部分，如喹啉，苯并恶唑，苯并噻唑，二甲基吲哚和与苯并[e]吲哚邻接的苯并[c，d]吲哚-1-鎓。被发现直接影响他们的光学和能量分布。在这项研究中，使用核磁共振和计算方法研究了光学性质与结构变化之间的关系。在DNA结合研究中利用了单次甲基花菁独特的扭曲构象，该新设计的传感器与DNA结合形式相比，结合在DNA凹槽中时显示出荧光增强。

  DOI：

  10.3390/molecules21010023

文献信息

• Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties
  作者：Eduardo Soriano、Cory Holder、Andrew Levitz、Maged Henary

  DOI：10.3390/molecules21010023

  日期：——

  have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles

  不对称的单次甲基花菁已广泛用作其他生物系统中核酸的探针。本文中，我们报告了七种单次甲基花青染料的合成，这些染料已成功制备成各种杂环部分，如喹啉，苯并恶唑，苯并噻唑，二甲基吲哚和与苯并[e]吲哚邻接的苯并[c，d]吲哚-1-鎓。被发现直接影响他们的光学和能量分布。在这项研究中，使用核磁共振和计算方法研究了光学性质与结构变化之间的关系。在DNA结合研究中利用了单次甲基花菁独特的扭曲构象，该新设计的传感器与DNA结合形式相比，结合在DNA凹槽中时显示出荧光增强。
• Method and Reagent for Measuring Nitroreductase Enzyme Activity
  申请人：West Richard Martin

  公开号：US20080317674A1

  公开（公告）日：2008-12-25

  Disclosed are nitro-substituted squaraine reporter dyes and methods using such dyes for detecting nitroreductase enzyme activity and nitroreductase gene expression in cellular assays. The dyes are of the structure: in which Z 1 and Z 2 independently represent a phenyl or a naphthyl ring system; X and Y are selected from oxygen, sulphur, —CH═CH— and the group: R 1 and R 2 are selected from C 1 -C 4 alkyl, —(CH 2 ) n —P, —(CH 2 ) 2 —O} p —R 6 and group W; where P is selected from COOR 7 , SO 3 − and OH, W is mono- or di-substituted nitrobenzyl, R 6 is methyl or ethyl, R 7 is selected from H, C 1 -C 4 alkyl and CH 2 OC(O)R 8 , where R 8 is methyl, or t-butyl, n is an integer from 1 to 10, and p is an integer from 1 to 3; R 3 and R 4 are selected from hydrogen, NO 2 , halogen, SO 3 − , C 1 -C 4 alkoxy and —(CH 2 ) m , —COOR 7 ; where R 7 is hereinbefore defined and m is 0 or an integer from 1 to 5; R 5 is C 1 -C 6 alkyl optionally substituted with COOR 7 , SO 3 − , or OH; where R 7 is hereinbefore defined; and at least one of groups R 1 , R 2 , R 3 and R 4 comprises at least one N0 2 group. Also provided are methods for screening for a test agent whose effect upon nitroreductase enzyme activity and nitroreductase gene expression is to be determined.

  本发明涉及硝基取代的方酰亚胺报告染料，以及使用该染料在细胞分析中检测硝基还原酶酶活性和硝基还原酶基因表达的方法。该染料的结构为：其中，Z1和Z2分别表示苯环或萘环系统；X和Y选择自氧、硫、—CH═CH—和组：R1和R2选择自C1-C4烷基、—(CH2)n—P、—(CH2)2—O}p—R6和组W；其中，P选择自COOR7、SO3−和OH，W为单取代或二取代的硝基苯甲基，R6为甲基或乙基，R7选择自H、C1-C4烷基和CH2OC(O)R8，其中，R8选择为甲基或叔丁基，n为1至10的整数，p为1至3的整数；R3和R4选择自氢、NO2、卤素、SO3−、C1-C4烷氧基和—(CH2)m、—COOR7，其中，R7如前所述，m为0或1至5的整数；R5为C1-C6烷基，可选地取代为COOR7、SO3−或OH，其中，R7如前所述；且R1、R2、R3和R4中至少有一个含有至少一个NO2基团。本发明还提供了一种筛选测试剂的方法，以确定其对硝基还原酶酶活性和硝基还原酶基因表达的影响。
• METHOD AND REAGENT FOR MEASURING NITROREDUCTASE ENZYME ACTIVITY
  申请人：WEST RICHARD MARTIN

  公开号：US20090325209A1

  公开（公告）日：2009-12-31

  Disclosed are nitro-substituted squaraine reporter dyes and methods using such dyes for detecting nitroreductase enzyme activity and nitroreductase gene expression in cellular assays. The dyes are of the structure: in which Z 1 and Z 2 independently represent a phenyl or a naphthyl ring system; X and Y are selected from oxygen, sulphur, —CH═CH— and the group: R 1 and R 2 are selected from C 1 -C 4 alkyl, —(CH 2 ) n —P, —(CH 2 ) 2 —O} p —R 6 and group W; where P is selected from COOR 7 , SO 3 − and OH, W is mono- or di-substituted nitrobenzyl, R 6 is methyl or ethyl, R 7 is selected from H, C 1 -C 4 alkyl and CH 2 OC(O)R 8 , where R 8 is methyl, or t-butyl, n is an integer from 1 to 10, and p is an integer from 1 to 3; R 3 and R 4 are selected from hydrogen, NO 2 , halogen, SO 3 − , C 1 -C 4 alkoxy and —(CH 2 ) m —COOR 7 ; where R 7 is hereinbefore defined and m is 0 or an integer from 1 to 5; R 5 is C 1 -C 6 alkyl optionally substituted with COOR 7 , SO 3 − , or OH; where R 7 is hereinbefore defined; and at least one of groups R 1 , R 2 , R 3 and R 4 comprises at least one NO 2 group. Also provided are methods for screening for a test agent whose effect upon nitroreductase enzyme activity and nitroreductase gene expression is to be determined.

  本发明涉及硝基取代的方酰菁报告染料以及使用这些染料在细胞分析中检测硝基还原酶酶活性和硝基还原酶基因表达的方法。该染料具有以下结构：其中Z1和Z2独立地表示苯环或萘环系统；X和Y选自氧、硫、-CH═CH-和以下基团：R1和R2选自C1-C4烷基、-(CH2)n-P、-(CH2)2-O}p-R6和基团W；其中P选自COOR7、SO3-和OH，W是单取代或双取代的硝基苯甲基，R6是甲基或乙基，R7选自H、C1-C4烷基和CH2OC(O)R8，其中R8是甲基或叔丁基，n为1至10的整数，p为1至3的整数；R3和R4选自氢、NO2、卤素、SO3-、C1-C4烷氧基和-(CH2)m-COOR7；其中R7如上定义，m为0或1至5的整数；R5是C1-C6烷基，可选地被COOR7、SO3-或OH取代；其中R7如上定义；且R1、R2、R3和R4中至少有一个包含至少一个NO2基团。此外，还提供了用于筛选测试剂的方法，该测试剂的作用是确定其对硝基还原酶酶活性和硝基还原酶基因表达的影响。
• Method and reagent for measuring nitroreductase enzyme activity
  申请人：GE Healthcare UK Limited

  公开号：US07579140B2

  公开（公告）日：2009-08-25

  Disclosed are nitro-substituted squaraine reporter dyes and methods using such dyes for detecting nitroreductase enzyme activity and nitroreductase gene expression in cellular assays. The dyes are of the structure: in which Z1 and Z2 independently represent a phenyl or a naphthyl ring system; X and Y are selected from oxygen, sulphur, —CH═CH— and the group: R1 and R2 are selected from C1-C4 alkyl, —(CH2)n—P, —(CH2)2—O}p—R6 and group W; where P is selected from COOR7, SO3− and OH, W is mono- or di-substituted nitrobenzyl, R6 is methyl or ethyl, R7 is selected from H, C1-C4 alkyl and CH2OC(O)R8, where R8 is methyl, or t-butyl, n is an integer from 1 to 10, and p is an integer from 1 to 3; R3 and R4 are selected from hydrogen, NO2, halogen, SO3−, C1-C4 alkoxy and —(CH2)m—COOR7; where R7 is hereinbefore defined and m is 0 or an integer from 1 to 5; R5 is C1-C6 alkyl optionally substituted with COOR7, SO3−, or OH; where R7 is hereinbefore defined; and at least one of groups R1, R2, R3 and R4 comprises at least one NO2 group. Also provided are methods for screening for a test agent whose effect upon nitroreductase enzyme activity and nitroreductase gene expression is to be determined.

  本发明涉及一种硝基取代的方酰亚胺报告染料以及使用该染料在细胞测定中检测硝基还原酶酶活性和硝基还原酶基因表达的方法。该染料的结构为：其中Z1和Z2分别表示苯环或萘环系统；X和Y选自氧、硫、—CH═CH—和该组：R1和R2选自C1-C4烷基，—(CH2)n—P，—(CH2)2—O}p—R6和组W；其中P选自COOR7、SO3−和OH，W为单取代或双取代的硝基苯甲基，R6为甲基或乙基，R7选自H、C1-C4烷基和CH2OC(O)R8，其中R8为甲基或叔丁基，n为1到10的整数，p为1到3的整数；R3和R4选自氢、NO2、卤素、SO3−、C1-C4烷氧基和—(CH2)m—COOR7，其中R7如前所述，m为0或1到5的整数；R5为C1-C6烷基，可选地取代为COOR7、SO3−或OH，其中R7如前所述；且R1、R2、R3和R4中至少有一个组含有至少一个NO2基团。还提供了用于筛选测试剂的方法，该测试剂的作用是确定其对硝基还原酶酶活性和硝基还原酶基因表达的影响。
• A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels
  作者：Narasimhachari Narayanan、Gabor Patonay

  DOI：10.1021/jo00113a018

  日期：1995.4

  A new uncatalyzed synthesis of heptamethine cyanine dyes is described. The reaction involves heating a mixture of N-alkyl-substituted quaternary salts derived from 2,3,3-trimethylindole or 2,3,3-trimethylbenzindole and 2-chloro-1-formyl-3-(hydroxymethylene)cyclohex-1-ene to reflux in a mixture of 1-butanol and benzene (7:3) as solvent. No catalyst is used, and water is removed as an azeotrope. The resulting chloro compounds possess strong absorption and fluorescence properties in the near-infrared region and are converted to dyes bearing reactive functionalities such as hydroxy and isothiocyanate groups useful as fluorescent tags for nucleic acids and proteins. Several symmetric and nonsymmetric dyes have been synthesized in high yields.