5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid methyl ester | 153120-93-5

• 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: 5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid methyl ester
• 英文别名: Methyl 5-amino-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoate
• CAS: 153120-93-5
• 化学式: C₂₁H₁₅NO₅
• 分子量: 361.354
• InChiKey: HKZXUYSTCXAMAC-UHFFFAOYSA-N

物化性质

• 沸点：
  688.9±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid methyl ester 在 氧气 、 氧化亚氮 作用下， 以78%的产率得到荧光素甲酯
  参考文献：
  名称：

  基于芳族伯单胺脱氨的一氧化氮开启荧光探针

  摘要：

  稳定，水溶性且不发荧光的FA-OMe可以感知一氧化氮（NO），并通过芳香族伯胺的还原性脱氨基反应形成强荧光产物dA-FA-OMe。该反应伴随着荧光量子产率从1.5至88.8％的显着增加。本研究提出了FA-OMe的NO脱氨机理。通过抑制光致电子传递（PeT）来执行打开的荧光信号，这由形成FA-OMe和dA-FA-OMe的组分的密度泛函理论（DFT）计算得到证明。此外，FA-OMe在生理pH下显示出水溶性和良好的稳定性。此外，选择性研究表明，FA-OMe对NO的特异性高于其他活性氧/氮物种。在一项内生的NO检测研究中，用脂多糖（LPS）预处理Raw 264.7鼠巨噬细胞增加FA-OMe的孵育时间可能会导致荧光强度图像增强。此外，扩散/定位细胞成像研究表明，FA-OMe可能被捕获在Raw 264.7细胞中。这些细胞成像结果表明，FA-OMe可用作开启荧光传感器，用于检测内源性生成的NO。

  DOI：

  10.1021/ic300379u
• 作为产物：
  描述：

  4-硝基荧光素 在 sodium sulfide 、 sodium hydrogensulfide 、 硫酸 作用下， 以 水 为溶剂， 反应 64.0h， 生成 5-amino-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid methyl ester
  参考文献：
  名称：

  核苷酸。第LXXI部分†

  摘要：

  开发了一种新的标记技术，该技术通过氨基甲酰基接头将荧光素直接连接到核碱基的氨基上。氨基首先转化为苯氧基羰基衍生物（10，15，19，58），它在温和条件下反应，用5-氨基荧光素，得到相应的Ñ - [（荧光素-5-基氨基）羰基]衍生物（11 - 14 ，16，17，20，59，60）。将5-氨基荧光素残基引入适当保护的腺苷-腺苷二聚体（39，40）和三聚体（50）工作良好，并且这些均一地封闭的前体的最终脱保护导致用DBU（1,8-二氮杂双环[5.4.0] undec-7-ene）处理，一步到二聚体41和三聚体51。适当保护的单体亚磷酰胺结构单元（75）的合成更加困难，因为将2-（4-硝基苯基）乙基残基引入59中的荧光素部分主要导致三取代，从而得到包括尿素官能团的61。腺苷二聚体66和三聚体67的形成通过亚磷酰胺化学反应以通常的方式进行；参见表1。然而，脱保护67与DBU是不完整的，因为Ø发现

  DOI：

  10.1002/hlca.200390186

文献信息

• Rational Design Principle for Modulating Fluorescence Properties of Fluorescein-Based Probes by Photoinduced Electron Transfer
  作者：Tetsuo Miura、Yasuteru Urano、Kumi Tanaka、Tetsuo Nagano、Kei Ohkubo、Shunichi Fukuzumi

  DOI：10.1021/ja035282s

  日期：2003.7.1

  to be finely controlled by the rate of photoinduced electron transfer from the benzoic acid moiety (electron donor) to the singlet excited state of the xanthene moiety (electron acceptor fluorophore). The occurrence of photoinduced electron transfer is clearly evidenced by transient absorption spectra showing bands due to the radical cation of the electron donor moiety and the radical anion of the xanthene

  基于荧光素的探针的荧光特性显示出通过光诱导电子从苯甲酸部分（电子供体）到呫吨部分（电子受体荧光团）的单线激发态的速率进行精细控制。在激光闪光光解实验中观察到，由于电子供体部分的自由基阳离子和呫吨部分的自由基阴离子，瞬态吸收光谱显示谱带清楚地证明了光致电子转移的发生。光致电子转移率和反向电子转移率遵循电子转移率对驱动力的马库斯抛物线依赖性。
• DINITROSYL IRON COMPLEX, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, COMPOSITE MATERIAL COMPRISING THE SAME, AND USES THEREOF
  申请人：Chung Yuan Christian University

  公开号：US20180208616A1

  公开（公告）日：2018-07-26

  Disclosed herein are novel compounds of formula (I) and (II), each of which may serve as a reagent to deliver nitric oxide (NO) and a therapeutic agent to treat NO-associated diseases. Also disclosed are a pharmaceutical composition comprising the compound of formula (I) or (II), a composite material comprising the compound of formula (I) or (II), and the uses thereof.

  本文披露了化学式(I)和(II)的新化合物，每个化合物可作为试剂传递一氧化氮(NO)和治疗剂以治疗与NO相关的疾病。还披露了含有化学式(I)或(II)的化合物的制药组合物，含有化学式(I)或(II)的复合材料及其用途。
• Dinitrosyl iron complex, pharmaceutical composition comprising the same, composite material comprising the same, and uses thereof
  申请人：Chung Yuan Christian University

  公开号：US10538545B2

  公开（公告）日：2020-01-21

  Disclosed herein are novel compounds of formula (I) and (II), each of which may serve as a reagent to deliver nitric oxide (NO) and a therapeutic agent to treat NO-associated diseases. Also disclosed are a pharmaceutical composition comprising the compound of formula (I) or (II), a composite material comprising the compound of formula (I) or (II), and the uses thereof.

  本文公开了新型的式(I)和(II)化合物，每种化合物都可作为一种试剂来递送一氧化氮（NO）和一种治疗剂来治疗与 NO 相关的疾病。还公开了包含式（I）或（II）化合物的药物组合物、包含式（I）或（II）化合物的复合材料及其用途。
• A New Type of Fluorescence Labeling of Nucleosides, Nucleotides and Oligonucleotides
  作者：Harald Sigmund、Thomas Maier、Wolfgang Pfleiderer

  DOI：10.1080/07328319708002935

  日期：1997.5

  Fluorescein has been coupled to the amino groups of the common nucleosides via a carbamoyl spacer to form a new type of conjugates. The corresponding phosphoramidites have been prepared with Npe and Npeoc protecting groups for application in oligonucleotide synthesis. Hybridizations have been studied in dependence of the fluorescing label as well as fluorescence quantum yields and fluorescence anisotropy effects.
• PERFLUORINATED COMPOUNDS FOR THE NON-VIRAL TRANSFER OF NUCLEIC ACIDS
  申请人：Schäfer Konstanze

  公开号：US20140065223A1

  公开（公告）日：2014-03-06

  The invention relates to a compound of general formula (I): A-B-C(F, G′)-D-E-F-G-A′ or a structure of general formula (II): A-B-C-(F′, G′)-D-B-E-F-G-A′ (II), wherein -A is at least one molecule selected from the group of the perfluorocarbons (PFCs), perfluorinated silicon compounds, and/or further perfluorinated compounds, -B is at least one predetermined breaking point in the form of a physically, chemically, or enzymatically severable bond, -C is absent or at least one linker molecule, -D is absent or at least one spacer molecule, -E is at least one molecule selected from the group containing nucleobases, nucleosides, nucleotides, oligonucleotides, nucleic, acids, modified nucleobases, modified nucleosides, modified nucleotides, modified oligonucleotides, modified nucleic acids, monomers of peptide nucleic acids, oligomers or peptide nucleic acids and peptide nucleic acids or other nucleic acid analogs, -F, F′ is absent or at least one ligand, -G, G′ is absent or at least one marker molecule, -A′ is absent or has the meaning of A, and wherein the compounds i), ii), iii), iv), v), vi) are excluded. The invention farther relates to the use of said compound for the non-viral transfer of molecule E into a cell, to a pharmaceutical composition containing said compound, and to the use of said pharmaceutical composition.