6-nitro-N-methyl-2-quinaldinium iodide | 59105-87-2

• 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
• 英文名称: 6-nitro-N-methyl-2-quinaldinium iodide
• 英文别名: 1,2-dimethyl-6-nitro-quinolinium; iodide；1,2-Dimethyl-6-nitro-chinolinium; Jodid；Quinolinium, 1,2-dimethyl-6-nitro-, iodide；1,2-dimethyl-6-nitroquinolin-1-ium;iodide
• CAS: 59105-87-2
• 化学式: C₁₁H₁₁N₂O₂*I
• 分子量: 330.125
• InChiKey: LSWBGEANPGMYSI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-nitro-N-methyl-2-quinaldinium iodide 、 2-(2-acetanilidovinyl)-1,3,3-trimethyl-3H-indolium iodide 在 吡啶 作用下， 生成 1-(1-methyl-6-nitro-[2]quinolyl)-3-(1,3,3-trimethyl-3H-indol-2-yl)-trimethinium ; iodide
  参考文献：
  名称：

  Piljugin; Krainer, Zhurnal Obshchei Khimii, 1953, vol. 23, p. 634,638; engl. Ausg. S. 661, 666

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-6-硝基喹啉 、 碘甲烷 在 乙酸乙酯 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以The product was obtained as a yellow/green solid (147 mg, 16.8%)的产率得到6-nitro-N-methyl-2-quinaldinium iodide
  参考文献：
  名称：

  METHOD AND REAGENT FOR MEASURING NITROREDUCTASE ENZYME ACTIVITY

  摘要：

  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。

  公开号：

  US20090325209A1

文献信息

• 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、—( )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 OC(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—( )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 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：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，—( )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 OC(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—( )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 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。
• Synthesis of Novel Quinaldine-Based Squaraine Dyes:  Effect of Substituents and Role of Electronic Factors
  作者：Kuthanapillil Jyothish、Kalliat T. Arun、Danaboyina Ramaiah

  DOI：10.1021/ol048411y

  日期：2004.10.1

  [GRAPHICS]Condensation of squaric acid with quinaldinium salts containing electron-donating substituents gave only the semisquaraines. However, with salts possessing electronegative and electron-withdrawing groups, the squaraine dyes were isolated in quantitative yields. The semisquaraines formed undergo condensation with highly nucleophilic salts yielding the unsymmetrical squaraine dyes. These results demonstrate the role of electronic factors and provide valuable information for the design of efficient squaraine-based sensitizers that can have potential applications in photodynamic therapy.
• Lepikhova,S.V.; Pilygin,G.T., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2323 - 2327
  作者：Lepikhova,S.V.、Pilygin,G.T.

  DOI：——

  日期：——
• Synthesis and antimicrobial properties of some quinoline derivatives
  作者：P. V. Prisyazhnyuk、V. K. Patratii、N. G. Prodanchuk、K. G. Tashchuk、S. D. Fedoryak

  DOI：10.1007/bf00760705

  日期：1984.4