4-(naphth-2-yl)-1,3-dihydroxybenzene | 1271736-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(naphth-2-yl)-1,3-dihydroxybenzene
• 英文别名: 1-(2-naphthyl)-2,4-benzenediol；4-Naphthalen-2-ylbenzene-1,3-diol
• CAS: 1271736-97-0
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: FXIGCQJPZAFCPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(naphth-2-yl)-1,3-dihydroxybenzene 在 sodium phosphate dibasic dodecahydrate 、 potassium nitrososulfonate 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 以53%的产率得到5-(2-naphthyl)-2-hydroxy-2,5-cyclohexadiene-1,4-dione
  参考文献：
  名称：

  Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

  摘要：

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.028
• 作为产物：
  描述：

  2-萘硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.42h， 生成 4-(naphth-2-yl)-1,3-dihydroxybenzene
  参考文献：
  名称：

  Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

  摘要：

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.028

文献信息

• Energy transfer dye containing an aromatic-substituted xanthene dye as donor dye and/or acceptor dye
  申请人：Applera Corporation

  公开号：EP1441011A1

  公开（公告）日：2004-07-28

  A class of aromatic-substituted xanthene compounds useful as fluorescent dyes is disclosed, the compounds having general structure (I), where Y1 and Y2 taken separately are selected from the group consisting of hydroxyl, oxygen, imminium, linking group and amine, or Y1 taken together with R2 is cyclic imine, or Y2 taken together with R3 is cyclic amine; R2, R3, R5, and R7 taken separately are selected from the group consisting of hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, imminium, amido, nitrile, lower alkoxy, phenyl, and linking group; R1 taken separately is selected from the group consisting of phenyl, substituted phenyl, polycyclic aromatic, substituted polycyclic aromatic, linking-group and electron-rich heterocycle, or when taken together with R7 is selected from the group consisting of electron-rich heterocycle and indene; R4 taken separately is selected from the group consisting of amino, amido, phenyl, substituted phenyl, polycyclic aromatic, substituted polycyclic aromatic, indene, linking group and electron-rich heterocycle, or when taken together with R5 is selected from the group consisting of phenyl, substituted phenyl, polycyclic aromatic, substituted polycyclic aromatic, indene, and electron rich heterocycle; and R6 is selected from the group consisting of acetylene, lower alkyl, lower alkene, cyano, phenyl, substituted phenyl, and heterocyclic aromatic. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labelled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, and polynucleotides. In an additional aspect, the invention includes methods utilising such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.

  本发明公开了一类可用作荧光染料的芳香族取代的氧杂蒽化合物，该化合物具有一般结构(I)，其中Y1和Y2分别选自羟基、氧、锇、连接基团和胺组成的组，或Y1与R2一起为环状亚胺，或Y2与R3一起为环状胺；R2、R3、R5 和 R7 分别选自氢、氟、氯、低级烷基、低级烯基、低级炔基、磺酸盐、砜、氨基、铵、酰胺、腈、低级烷氧基、苯基和连接基团组成的组；R1 单独选自苯基、取代苯基、多环芳香族、取代多环芳香族、连接基团和富电子杂环组成的组，或与 R7 结合选自富电子杂环和茚组成的组；R4 单独取自氨基、酰胺、苯基、取代苯基、多环芳香族、取代多环芳香族、茚、连接基团和富电子杂环组成的组，或与 R5 一起取自苯基、取代苯基、多环芳香族、取代多环芳香族、茚和富电子杂环组成的组；以及 R6 取自乙炔、低级烷基、低级烯烃、氰基、苯基、取代苯基和杂环芳香族组成的组。在另一方面，本发明包括合成上述染料化合物和中间体的方法。又一方面，本发明包括用不对称苯并氧杂蒽染料化合物标记的试剂，包括脱氧核苷酸、双脱氧核苷酸、磷酰胺和多核苷酸。在另一方面，本发明还包括利用此类染料化合物和试剂的方法，包括双脱氧多核苷酸测序和片段分析方法。
• [EN] AROMATIC-SUBSTITUTED XANTHENE DYES<br/>[FR] COLORANTS A BASE DE XANTHENE A SUBSTITUTION AROMATIQUE
  申请人：THE PERKIN-ELMER CORPORATION

  公开号：WO1999016832A1

  公开（公告）日：1999-04-08

  (EN) A class of aromatic-substituted xanthene compounds useful as fluorescent dyes is disclosed, the compounds having general structure (I), where Y1 and Y2 taken separately are selected from the group consisting of hydroxyl, oxygen, imminium, linking group and amine, or Y1 taken together with R2 is cyclic imine, or Y2 taken together with R3 is cyclic amine; R2, R3, R5, and R7 taken separately are selected from the group consisting of hydrogen, fluorine, chlorine, lower alkyl, lower alkene, lower alkyne, sulfonate, sulfone, amino, imminium, amido, nitrile, lower alkoxy, phenyl, and linking group; R1 taken separately is selected from the group consisting of phenyl, substituted phenyl, polycyclic aromatic, substituted polycyclic aromatic, linking group and electron-rich heterocycle, or when taken together with R7 is selected from the group consisting of electron-rich heterocycle and indene; R4 taken separately is selected from the group consisting of amino, amido, phenyl, substituted phenyl, polycyclic aromatic, substituted polycyclic aromatic, indene, linking group and electron-rich heterocycle, or when taken together with R5 is selected from the group consisting of phenyl, substituted phenyl, polycyclic aromatic, substituted polycyclic aromatic, indene, and electron-rich heterocycle; and R6 is selected from the group consisting of acetylene, lower alkyl, lower alkene, cyano, phenyl, substituted phenyl, and heterocyclic aromatic. In another aspect, the invention includes methods for synthesizing the above dye compounds and intermediates. In yet another aspect, the present invention includes reagents labeled with the asymmetric benzoxanthene dye compounds, including deoxynucleotides, dideoxynucleotides, phosphoramidites, and polynucleotides. In an additional aspect, the invention includes methods utilizing such dye compounds and reagents including dideoxy polynucleotide sequencing and fragment analysis methods.(FR) A invention concerne une classe de composés à base de xanthène à substitution aromatique utiles en tant que colorants fluorescents, lesquels composés présentent une structure générale (I), dans laquelle Y1 et Y2, pris séparément, sont sélectionnés dans le groupe constitué par hydroxyle, oxygène, imminium, groupe de liaison et amine, ou Y1, pris avec R2, représente imine cyclique, ou Y2, pris avec R3, représente amine cyclique; R2, R3, R5 et R7, pris séparément, sont sélectionnés dans le groupe constitué par hydrogène, fluor, chlore, alkyle inférieur, alcène inférieur, alcyne inférieur, sulfonate, sulfone, amino, imminium, amido, nitrile, alcoxy inférieur, phényle et groupe de liaison; R1, pris séparément, est sélectionné dans le groupe constitué par phényle, phényle substitué, aromatique polycyclique, aromatique polycyclique substitué, groupe de liaison, et hétérocycle riche en électrons, ou, lorsqu'il est pris avec R7, est sélectionné dans le groupe constitué par hétérocycle riche en électrons et indène; R4, pris séparément, est sélectionné dans le groupe constitué par amino, amido, phényle, phényle substitué, aromatique polycyclique, aromatique polycyclique substitué, indène, groupe de liaison et hétérocycle riche en électrons, ou, lorsqu'il est pris avec R5, est sélectionné dans le groupe constitué par phényle, phényle substitué, aromatique polycyclique, aromatique polycyclique substitué, indène et hétérocycle riche en électrons; et R6 est sélectionné dans le groupe constitué par acétylène, alkyle inférieur, alcène inférieur, cyano, phényle, phényle substitué et aromatique hétérocyclique. Dans un deuxième aspect, l'invention concerne des procédés de synthèse de ces composés de colorant et de leurs intermédiaires. Dans un troisième aspect, la présente invention concerne des réactifs marqués avec ces composés de colorant à base de benzoxanthène asymétrique, y compris des désoxynucléotides, des didésoxynucléotides, des phosphoramidites et des polynucléotides. Dans un quatrième aspect, l'invention concerne des procédés utilisant ces composés de colorant et ces réactifs, notamment des procédés de séquençage de polynucléotides didésoxy et d'analyse de fragments.

  披露了一类被用作荧光染料的芳香取代的xanthene化学物质，其一般结构为(I)，其中Y1和Y2单独选取自含有的小分子基团（包括羟基、氧、邻近离子、 conjugated基团和胺），或Y1与R2一起构成离环氮；Y2与R3一起构成离环氨； R2、R3、R5和R7单独选取自含有的小分子基团（包括氢、氟、氯、较低的碳链烷基、较低的碳链烯基、较低的碳链三键基团、硫酸酯、 sulfone、氨基、邻近离子、酰胺、腈、较低的氧基、苯基和连接基团）； R1单独选取自含有的小分子基团（包括苯基、取代苯基、多环芳香基、取代多环芳香基、连接基团、和富电子的杂环）；当R1与R7一起选取时， R7选取自富电子的杂环和烷话题烯基（即类ilinearene的类比）； R4单独选取自含有的小分子基团（包括氨基、酰胺、苯基、取代苯基、多环芳香基、取代多环芳香基、烷话题烯基、连接基团和富电子的杂环）；当R4与R5一起选取时， R5选取自苯基、取代苯基、多环芳香基、取代多环芳香基、烷话题烯基和富电子的杂环； R6选取自含有的小分子基团（包括碳碳三键、较低的碳链烷基、较低的碳链烯基、羰基、苯基、取代苯基和杂环芳香基）中的成员。 从另一个方面，本发明还涉及合成上述染料化合物及其中间体的方法。 从另一个方面，本发明还涉及标注有不对称苯基xanthene染料的试剂，包括脱氧核苷酸、脱氧核苷酸二磷酸、磷酸二酯 amidites和多核苷酸。 从另一个方面，本发明还涉及利用这些染料和试剂的方法，其中包含多核苷酸二磷酸酸脱氧序列分析方法。
• AROMATIC-SUBSTITUTED XANTHENE DYES
  申请人：Applera Corporation

  公开号：EP1019453B1

  公开（公告）日：2004-03-31
• US6008379A
  申请人：——

  公开号：US6008379A

  公开（公告）日：1999-12-28
• Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues
  作者：Carmen Petronzi、Rosanna Filosa、Antonella Peduto、Maria Chiara Monti、Luigi Margarucci、Antonio Massa、Simona Francesca Ercolino、Valentina Bizzarro、Luca Parente、Raffaele Riccio、Paolo de Caprariis

  DOI：10.1016/j.ejmech.2010.11.028

  日期：2011.2

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.