2-(10-hydroxy-3-phenylaminomethyl-3H-benzo[c]xanthen-7-yl)benzoic acid

• 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: 2-(10-hydroxy-3-phenylaminomethyl-3H-benzo[c]xanthen-7-yl)benzoic acid
• 英文别名: SNF；2-(10-Hydroxy-11-methyl-3-oxobenzo[c]xanthen-7-yl)benzoic acid；2-(10-hydroxy-11-methyl-3-oxobenzo[c]xanthen-7-yl)benzoic acid
• 化学式: C₂₅H₁₆O₅
• 分子量: 396.399
• InChiKey: IMPDVGDSMQZDCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(10-hydroxy-3-phenylaminomethyl-3H-benzo[c]xanthen-7-yl)benzoic acid 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (2R,2'R)-3,3'-((((11-methyl-3'-oxo-3'H-spiro[benzo[c]xanthene-7,1'-isobenzofuran]-3,10-diyl)bis(oxy))bis(3-oxopropane-3,1-diyl))bis(sulfanediyl))bis(2-aminopropanoic acid)
  参考文献：
  名称：

  A seminaphthofluorescein-based fluorescent chemodosimeter for the highly selective detection of cysteine

  摘要：

  一种荧光化学探针用于检测半胱氨酸，其基于串联的共轭加成和分子内环化反应。该方法对半胱氨酸表现出优异的选择性，相较于其他生物硫醇如同型半胱氨酸和谷胱甘肽。

  DOI：

  10.1039/c2ob25178g
• 作为产物：
  描述：

  苯酐 在 aluminum (III) chloride 、 甲烷磺酸 作用下， 生成 2-(10-hydroxy-3-phenylaminomethyl-3H-benzo[c]xanthen-7-yl)benzoic acid
  参考文献：
  名称：

  A seminaphthofluorescein-based fluorescent chemodosimeter for the highly selective detection of cysteine

  摘要：

  一种荧光化学探针用于检测半胱氨酸，其基于串联的共轭加成和分子内环化反应。该方法对半胱氨酸表现出优异的选择性，相较于其他生物硫醇如同型半胱氨酸和谷胱甘肽。

  DOI：

  10.1039/c2ob25178g

文献信息

• [EN] SELECTIVE DETECTION OF THIOLS<br/>[FR] DÉTECTION SÉLECTIVE DE THIOLS
  申请人：OREGON STATE

  公开号：WO2013126816A1

  公开（公告）日：2013-08-29

  Probes for selectively detecting compounds comprising a thiol group and an amino group ("thiols") are disclosed. Exemplary thiols include cysteine, homocysteine, and glutathione. Embodiments of the disclosed probes produce a detectable change in absorbance spectrum and/or emission spectrum when reacted with one or more thiols in solution. Methods and kits for performing the detection also are disclosed. The probes have a general formula where each bond depicted as "¯¯¯¯¯¯ " is a single or double bond; R1, R3-R6 and R8 independently are hydrogen, hydroxyl, thiol, lower alkyl, carboxyalkyl, amino, alkoxy, or halogen; R2 is an α,β-unsaturated aliphatic ester; R7 is oxygen, sulfur, hydrogen, hydroxyl, thiol, lower alkyl, carboxyalkyl, amino, alkoxy, or halogen, or R7 and R8 together form a cycloalkyl or aryl ring; X1 is CH2, S, NH, O, Se, Si(CH3)2, Ge(CH3)2, Sn(CH3)2, or C(CH3)2; and X2 is CH, CH2, N, NH, or CR9 where R9 is aryl.

  本文揭示了用于选择性检测含有巯基和氨基（“巯基”）的化合物的探针。示例巯基包括半胱氨酸，同型半胱氨酸和谷胱甘肽。所述探针的实施例在与一个或多个溶液中的巯基反应时，产生可检测的吸收光谱和/或发射光谱的变化。本文还揭示了执行检测的方法和工具包。探针具有一般公式，其中每个表示为“¯¯¯¯¯¯”的键是单键或双键；R1、R3-R6和R8独立地是氢、羟基、巯基、低碳基、羧基烷基、氨基、烷氧基或卤素；R2是α，β-不饱和脂肪酸酯；R7是氧、硫、氢、羟基、巯基、低碳基、羧基烷基、氨基、烷氧基或卤素，或R7和R8一起形成环烷基或芳基环；X1是CH2、S、NH、O、Se、Si（CH3）2、Ge（CH3）2、Sn（CH3）2或C（CH3）2；X2是CH、CH2、N、NH或CR9，其中R9是芳基。
• SELECTIVE DETECTION OF THIOLS
  申请人：OREGON STATE BOARD OF HIGHER EDUCATION ON BEHALF OF PORTLAND STATE UNIVERSITY

  公开号：US20150010938A1

  公开（公告）日：2015-01-08

  Probes for selectively detecting compounds comprising a thiol group and an amino group (“thiols”) are disclosed. Exemplary thiols include cysteine, homocysteine, and glutathione. Embodiments of the disclosed probes produce a detectable change in absorbance spectrum and/or emission spectrum when reacted with one or more thiols in solution. Methods and kits for performing the detection also are disclosed. The probes have a general formula where each bond depicted as “ ” is a single or double bond; R 1 , R 3 -R 6 and R 8 independently are hydrogen, hydroxyl, thiol, lower alkyl, carboxyalkyl, amino, alkoxy, or halogen; R 2 is an α,β-unsaturated aliphatic ester; R 7 is oxygen, sulfur, hydrogen, hydroxyl, thiol, lower alkyl, carboxyalkyl, amino, alkoxy, or halogen, or R 7 and R 8 together form a cycloalkyl or aryl ring; X 1 is CH 2 , S, NH, O, Se, Si(CH 3 ) 2 , Ge(CH 3 ) 2 , Sn(CH 3 ) 2 , or C(CH 3 ) 2 ; and X 2 is CH, CH 2 , N, NH, or CR 9 where R 9 is aryl.
• US9506929B2
  申请人：——

  公开号：US9506929B2

  公开（公告）日：2016-11-29
• A seminaphthofluorescein-based fluorescent chemodosimeter for the highly selective detection of cysteine
  作者：Xiaofeng Yang、Yixing Guo、Robert M. Strongin

  DOI：10.1039/c2ob25178g

  日期：——

  A fluorescent chemodosimeter for cysteine detection was developed based on a tandem conjugate addition and intramolecular cyclization reaction. The method exhibited an excellent selectivity for cysteine over other biothiols such as homocysteine and glutathione.

  一种荧光化学探针用于检测半胱氨酸，其基于串联的共轭加成和分子内环化反应。该方法对半胱氨酸表现出优异的选择性，相较于其他生物硫醇如同型半胱氨酸和谷胱甘肽。