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    • 1. 发明申请
    • PYRAZOLE-BASED CYANINE DYE CONTAINING QUATERNARY AMMONIUM CATION
    • US20120046474A1
    • 2012-02-23
    • US13318089
    • 2010-04-27
    • Naoyuki YamamotoTatsuo KurosawaSatoshi HasabaMatsuhiro Date
    • Naoyuki YamamotoTatsuo KurosawaSatoshi HasabaMatsuhiro Date
    • C07D403/06
    • C07D403/06C09B23/083
    • ProblemProvided is a novel cyanine dye derivative having high fluorescence intensity in a short wavelength region, a structure where a pyrazole skeleton and an indole skeleton are bound to a polymethine chain, and also a controllable migration velocity by further introducing a quaternary ammonium cation into a molecule having said structure.SolutionThe present invention is the invention of a compound represented by the general formula [1] or a salt thereof: [wherein R1 to R6 each independently represent an alkyl group having, as a substituent, a group represented by the general formula [101]: (wherein R101 to R104 each independently represent a hydrogen atom or an alkyl group of C1 to C3 and m represents an integer from 2 to 6, and two or three of R102 to R104 together with a nitrogen atom to which they are bound may form a heterocyclic ammonium cation); or a group derived from a carboxylic acid represented by the general formula [2] which may have an amide bond: —COOR12  [2] (wherein R12 represents a hydrogen atom, an alkyl group of C1 to C10, an alkali metal atom, an organic ammonium ion, an ammonium ion or anion); or an alkyl group which may have, as a substituent, a group derived from a sulfonic acid represented by the general formula [3] which may have an amide bond: —SO3R13  [3] (wherein R13 represents a hydrogen atom, an alkali metal atom, an organic ammonium ion, an ammonium ion or anion); R7 to R10 each independently represent an alkyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, an alkylsulfonyl group, an arylsulfonyl group, an amino group, a group derived from a carboxylic acid represented by the general formula [2], a group derived from a sulfonic acid represented by the general formula [3], a halogen atom, a hydrogen atom, a hydroxyl group, a cyano group or a nitro group; R11 represents a hydrogen atom, an alkyl group, an alkynyl group or an aryl group, and n represents an integer from 0 to 3, and at least one of R1 to R6 is an alkyl group having, as a substituent, a group represented by the general formula [101]].
    • 2. 发明授权
    • Pyrazole-based cyanine dye
    • US08921124B2
    • 2014-12-30
    • US12295189
    • 2007-03-30
    • Matsuhiro DateSatoshi HasabaNaoyuki Yamamoto
    • Matsuhiro DateSatoshi HasabaNaoyuki Yamamoto
    • G01N33/533C09B23/06C07D487/02G01N33/58C07D403/06C07D403/14C07D487/04C07D487/14C09B23/08
    • C09B23/06C07D403/06C07D403/14C07D487/04C07D487/14C09B23/083G01N33/533G01N33/582
    • PROBLEMProvided is a novel cyanine dye derivative with a pyrazole skeleton and an indole skeleton, having high sensitivity performance in a shorter wavelength region as compared with a conventional optical system, and showing high water solubility.SOLUTIONThe invention provides (1) a compound represented by the following general formula [50] and a salt thereof: [wherein R1 to R6 each independently represent a substituted or unsubstituted alkyl group which may have an amide bond; R7 to R10 each independently represent alkyl group, alkenyl group, alkynyl group, aryl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, alkylsulfonyl group, arylsulfonyl group, carbamoyl group, sulfamoyl group, ureido group or amino group, those groups being able to have substituents; a group represented by the general formula [2]: —COOR12  [2] (wherein R12 represents hydrogen atom, C1 to C10 alkyl group, alkali metal atom, organic ammonium ion, ammonium ion or anion); a group represented by the general formula [3]: —SO3R13  [3] (wherein R13 represents hydrogen atom, alkali metal atom, organic ammonium ion, ammonium ion or anion), halogen atom, aromatic heterocyclic thio group, hydrogen atom, hydroxyl group, cyano group, formyl group, thiol group or nitro group; R11 represents hydrogen atom, or alkyl group, alkenyl group, alkynyl group or aryl group, those groups being able to have substituents; and n represents an integer of from 0 to 3, provided that any of R1 and R2, R4 and R5, R1 and R6, and R2 and R4 may form a bivalent group with a group selected from —O— group, —S— group, —COO— group and groups represented by the general formulae [52] to [54]: (wherein R50 represents hydrogen atom, alkyl group, alkenyl group or aryl group, those groups being able to have substituents), and substituted or unsubstituted alkylene group; and in the case where said bivalent group is formed, at least one of R1 to R11, along with the bivalent group formed by any of R1 and R2, R4 and R5, R1 and R6, and R2 and R4, has the group represented by the general formula [2], the group represented by the general formula [3], amino group, hydroxyl group, thiol group or formyl group; and in the case where said bivalent group is not formed, at least one of R1 to R11 has the group represented by the general formula [2], the group represented by the general formula [3], amino group, hydroxyl group, thiol group or formyl group]; (2) a labeled compound obtained by subjecting the above compound to direct or indirect binding to a substance to be labeled, and (3) a method for labeling a substance to be labeled, comprising subjecting the above compound to direct or indirect binding to the substance to be labeled.