Indole phthalocyanine compound, preparation method therefor, and use thereof in tumor diagnosis imaging

A compound represented by general formula (IA) or a pharmaceutically acceptable salt thereof,

• wherein:
• X is C, O, S or N+;
• M− is an acid ion;
• n is 1 or 2, when X is one N+, n is 2, and when X is C, O or S, n is 1;
• R1 and R2 are each independently L1-L2-L3-Q;
• L1 is selected from the group consisting of bond, —(CH2)p—, —(CH2O)q—, —(CH2CH2O)v—, —(CH2O)q—(CH2)p—, —(CH2)p—(CH2O)q—, —(CH2)p—(CH2O)q—(CH2)p—, —(CH2CH2O)v—(CH2)p— and —(CH2CH2O)v—(CH2O)q—;
• L2 is selected from the group consisting of bond, aryl, heteroaryl, cycloalkyl and heterocyclyl;
• L3 is selected from the group consisting of bond, —(CH2)p—, —(CH2O)q—, —(CH2CH2O)v—, —(CH2O)q—(CH2)p—, —(CH2)p—(CH2O)q—, —(CH2)p—(CH2O)q—(CH2)p—, —(CH2CH2O)v—(CH2)p— and —(CH2CH2O)v—(CH2O)q—;
• Q is selected from the group consisting of R12, —OR13, —C(O)R12, —C(O)OR13, —C(O)NHR13, —SO3H and
• R12 is selected from the group consisting of hydrogen, halogen, amino, hydroxy, thiol, alkyl, alkylamino, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more groups selected from the group consisting of halogen, amino, cyano, hydroxy, thiol, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R13 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more groups selected from the group consisting of halogen, amino, cyano, hydroxy, thiol, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R3 and R4 are each independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, hydroxy, thiol, oxo, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R5 and R6 are each independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, hydroxy, thiol, oxo, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R7 is selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, thiol, oxo, alkyl, ORa, SRa, NRbRc, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R8 and R9 are each independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, thiol, oxo, alkyl, ORa, NRbRc, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, carboxy, ester, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R8a and R9a are each independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, hydroxy, thiol, oxo, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R8b and R9b are each independently selected from the group consisting of hydrogen, halogen, amino, nitro, cyano, hydroxy, thiol, oxo, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R10a, R10b, R10c and R10d are each independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, thiol, oxo, alkyl, ORa, NRbRc, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, carboxy, ester, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• or any two adjacent ones of R10a, R10b, R10c and R10d, together with the atoms to which they are attached, form an aryl or heteroaryl, and the aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, carboxy, ester, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R11a, R11b, R11c and R11d are each independently selected from the group consisting of hydrogen, halogen, nitro, cyano, hydroxy, thiol, oxo, alkyl, ORa, NRbRc, —SO3H, —S(O)2Ra, —C(O)ORa, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, carboxy, ester, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• or any two adjacent ones of R11a, R11b, R11c and R11d, together with the atoms to which they are attached, form an aryl or heteroaryl, and the aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, carboxy, ester, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• Ra is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, carboxy, ester, sulfonic group, —NHC(O)-L4-NRbRc, —OC(O)-L4-NRbRc, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• wherein -L4- is alkenylene;
• Rb and Rc are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl, wherein the alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally further substituted by one or more substituents selected from the group consisting of halogen, amino, oxo, thioxo, nitro, cyano, hydroxy, thiol, carboxy, ester, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• m is 0 or 1;
• p is an integer from 1 to 10;
• q is an integer from 1 to 10;
• v is an integer from 1 to 10.