1,3-Bis-(4-carboxy phenyl)-1H-indazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-Bis-(4-carboxy phenyl)-1H-indazole
• 英文别名: 4-[1-(4-carboxyphenyl)indazol-3-yl]benzoic acid
• 化学式: C₂₁H₁₄N₂O₄
• 分子量: 358.3
• InChiKey: BMQWKEGKRGSRMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  硝酸 、 硫酸 、 1,3-Bis-(4-carboxy phenyl)-1H-indazole 、 sodium hydroxide 在 ice 、 Brine 、 N,N-dimethylformamide methanol 作用下， 以 ice water 为溶剂， 反应 2.17h， 以yielding 153 mg (45 %) of 4k的产率得到4-[3-(4-carboxy-phenyl)-5-nitro-1H-indazol-1-yl]-benzoic Acid
  参考文献：
  名称：

  Fluorescent dyes (AIDA) for solid phase and solution phase screening

  摘要：

  该发明涉及公式(I)的新荧光染料，可用于高通量筛选，包括在固相和均相溶液中。

  公开号：

  US20050227299A1

文献信息

• FLUORESCENT DYES FOR SOLID PHASE AND SOLUTION PHASE SCREENING
  申请人：Novartis AG

  公开号：EP1140856A1

  公开（公告）日：2001-10-10
• US6207831B1
  申请人：——

  公开号：US6207831B1

  公开（公告）日：2001-03-27
• [EN] FLUORESCENT DYES FOR SOLID PHASE AND SOLUTION PHASE SCREENING<br/>[FR] COLORANTS FLUORESCENTS DESTINES AU CRIBLAGE DE PHASE SOLIDE ET DE PHASE SOLUTION
  申请人：NOVARTIS AG

  公开号：WO2000037448A1

  公开（公告）日：2000-06-29

  The invention relates to new fluorescent dyes of formula (I) which can be used in high throughput screening both, on the solid phase as well as in homogeneous solution. The new fluorescent dyes generically referred to as AIDA chemistry are suitable for various methods of solid phase and solution phase organic chemistry for synthesis of molecules to be investigated for therapeutic use in disease states. The molecules of therapeutic interest can be synthesized as fluorescent conjugates by two methods: (a) a solid support is loaded with a cleavable linker (acid-, base-, redox- or light sensitive) to which consecutively the fluorescent dye is attached. The dyes possess a second functionality, which serves as attachment point for spacer elements. The spacer bears a further functional group which us used as starting point of the synthesis of the molecules to be investigated; (b) the fluorescent dye can also be introduced as end-cap in the last synthesis step of a reaction sequence. The dyes described in the invention are chemically stable under a broad range of reaction conditions usually applied in solid phase and solution phase organic chemistry. The conjugates emit fluorescence in the visible and UV-spectral range on excitation at wavelengths of their absorption. These fluorescence properties allow for multiple applications in fluorescence based processes for the identification of inhibitors of molecular interactions and for the identification of molecules which bind to target macromolecules like peptides proteins, nucleic acids, carbohydrates etc. The fluorescence detection technologies used for monitoring binding of AIDA-conjugated compounds to macromolecules include conventional macroscopic techniques (ensemble averaging) which detect changes in fluorescence intensity, anisotropy(polarization), fluorescence resonance energy transfer, fluorescence lifetime, rotational correlation time as well as one- and two-dimensional single molecule spectroscopic techniques (SMS). Uses of the dye include solid phase and solution phase organic chemistry, low molecular weight compound labelling, peptide labelling, protein labelling, optical spectroscopy and fluorescence. Synthesis of functionalized dyes and of dye conjugates (on solid support and in solution) are disclosed.
• Fluorescent dyes (AIDA) for solid phase and solution phase screening
  申请人：——

  公开号：US20010005752A1

  公开（公告）日：2001-06-28

  The invention relates to new fluorescent dyes of formula (I) 1 which can be used in high throughput screening both, on the solid phase as well as in homogeneous solution. The new fluorescent dyes generically referred to as AIDA chemistry is suitable for various methods of solid phase and solution phase organic chemistry for synthesis of molecules to be investigated for therapeutic use in disease states. The molecules of therapeutic interest can be synthesized as fluorescent conjugates by two methods: (a) a solid support is loaded with a cleavable linker (acid-, base-, redox- or light sensitive) to which initially the fluorescent dye is attached. The dyes possess a second functionality, which serves as attachment point for spacer elements. The spacer bears a further functional group which is used as starting point of the synthesis of the molecules to be investigated; (b) the fluorescent dye can also be introduced as end-cap in the last synthesis step of a reaction sequence. The dyes described in the invention are chemically stable under a broad range of reaction conditions usually applied in solid phase and solution phase organic chemistry. The conjugates emit fluoresence in the visible and UV-spectral range on excitation at wavelengths of their absorption. These fluorescence properties allow for multiple applications in fluorescence based processes for the identification of inhibitors of molecular interactions and for the identification of molecules which bind to target macromolecules like peptides proteins, nucleic acids, carbohydrates etc. The fluorescence detection technologies used for monitoring binding of AIDA-conjugated compounds to macromolecules include conventional macroscopic techniques (ensemble averaging) which detect changes in fluorescence intensity, anisotropy(polarization), fluorescence resonance energy transfer, fluorescence lifetime, rotational correlation time as well as one- and twodimensional single molecule spectroscopic techniques (SMS). Uses of the dye include solid phase and solution phase organic chemistry, low molecular weight compound labelling, peptide labelling, protein labelling, optical spectroscopy and fluorescence. Synthesis of functionalized dyes and of dye conjugates (on solid support and in solution) are disclosed.

  本发明涉及一种新的荧光染料，其化学式为（I）1，可用于高通量筛选，包括固相和均相溶液。这种新的荧光染料通常被称为AIDA化学，适用于各种固相和溶液相有机化学方法，用于合成用于治疗疾病状态的分子。治疗感兴趣的分子可以通过两种方法合成为荧光共轭物：（a）将可剥离连接剂（酸、碱、氧化还原或光敏）附加到固定支持上，最初将荧光染料附加到连接剂上。这些染料具有第二个功能，用作间隔元素的附着点。间隔元素带有另一个功能基团，用作待研究分子合成的起点；（b）荧光染料也可以在反应序列的最后合成步骤中作为末端盖引入。本发明中描述的染料在固相和溶液相有机化学中通常应用的广泛反应条件下具有化学稳定性。共轭物在激发其吸收波长时在可见光和紫外光谱范围内发射荧光。这些荧光特性允许在多种荧光基于过程中应用，用于鉴定分子相互作用的抑制剂以及结合到目标大分子（如肽、蛋白质、核酸、碳水化合物等）的分子的鉴定。用于监测AIDA共轭化合物与大分子结合的荧光检测技术包括传统的宏观技术（集合平均），用于检测荧光强度、各向异性（极化度）、荧光共振能量转移、荧光寿命、旋转相关时间以及一维和二维单分子光谱技术（SMS）。染料的用途包括固相和溶液相有机化学、低分子量化合物标记、肽标记、蛋白质标记、光学光谱学和荧光。本发明还公开了功能化染料和染料共轭物（在固定支持和溶液中）的合成方法。