1,2-naphthoquinone based derivative and method of preparing the same

A compound represented by Formula (1) below or a pharmaceutically acceptable salt, hydrate, solvate, prodrug, tautomer, enantiomer, or pharmaceutically acceptable diastereomer thereof:

• wherein R1 and R2 are each independently hydrogen, a halogen, hydroxyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C4-C10 aryl, substituted or unsubstituted C4-C10 aryloxy, substituted or unsubstituted C2-C10 heteroaryl, —NO2, —NR′1R′2, —NR′1(CO(O)R′2), —NR′1 (C(O)NR′1R′2), —CO(O)R′1, —C(O)NR′1R′2, —CN, —SO(O)R′1, —SO(O)NR′1R′2, —NR′1 (SO(O)R′2), —CSNR′1R′2, or R1 and R2 form a ring structure of substituted or unsubstituted C4-C10 aryl through coupling or a ring structure of substituted or unsubstituted C2-C10 heteroaryl,
• where R′1 and R′2 are each independently hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C4-C10 aryl, substituted or unsubstituted C4-C10 aryloxy, substituted or unsubstituted C1-C8 heteroaryl, substituted or unsubstituted —(CR″1R″2)m′-C4-C10 aryl, substituted or unsubstituted —(CR″1R″2)m′-C4-C10 heteroaryl or substituted or unsubstituted NR″1R″2;
• where R″1 and R″2 are each independently hydrogen, or C1-C3 alkyl, or R″1 and R″2 form a ring structure of substituted or unsubstituted C4-C10 aryl through coupling;
• R3 is hydrogen, oxygen, a halogen, unsubstituted branched C3-C10 alkyl, substituted or unsubstituted C2-C20 alkene, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C8 heterocycloalkyl, substituted or unsubstituted C4-C10 aryl, substituted or unsubstituted C4-C10 aryloxy, substituted or unsubstituted C1-C10 heteroaryl, substituted or unsubstituted —(CR′5R′6)m—C4-C10 aryl, substituted or unsubstituted —(CR′5R′6)m—C4-C10 aryloxy, substituted or unsubstituted —(CR′5R′6)m—C1-C10 heteroaryl, substituted or unsubstituted —(CR′5R′6)m—NR′3R′4, substituted or unsubstituted —(CR′5R′6)m—C2-C10 heterocycloalkyl, substituted or unsubstituted —(CR′5R′6)m—OR′3, substituted or unsubstituted —(CR′5R′6)m(O)COR′3, —CO(O)R′3, —CONR′3R′4, —NR′3R′4, —NR′3(C(O)R′4);
• where R′3 and R′4 are each independently hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C4-C10 aryl, substituted or unsubstituted —(CR′5R′6)m—C4-C10 aryl, substituted or unsubstituted —(CR′5R′6)m—C4-C10 aryloxy, substituted or unsubstituted —(CR′5R′6)m—C1-C10 heteroaryl, —CO(O)R′″3, or R′3 and R′4 form a ring structure of substituted or unsubstituted C2-C10 heterocycloalkyl or substituted or unsubstituted C1-C10 heteroaryl through coupling;
• R′5 and R′6 are each independently hydrogen or C1-C3 alkyl;
• and R′″3 is C1-C6 alkyl;
• wherein a substituted group is at least one selected from the group consisting of hydroxy, a nitro group, a halogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C1-C10 alkoxy, C1-C10 alkoxycarbonyl, C3-C8 cycloalkyl, C2-C8 heterocycloalkyl, C4-C10 aryl, and C2-C10 heteroaryl;
• X1, X2, X3 and X4 are each independently C(H), CO, or N (R″3);
• X6 is O when X5 is N (R″4) and X6 is N (R″4) when X5 is O;
• where R″3 and R″4 are each independently hydrogen, substituted or unsubstituted C1-C6 alkyl, C1-C6 alkoxy, or substituted or unsubstituted —(CH2)n—C4-C6 aryl, and the substituted group is at least one selected from the group consisting of hydroxy, a halogen, and C1-C5 alkyl;
• m, m′, and n are each independently a natural number of 1 to 4;
• a heteroatom is at least one selected from N, O, and S;
• and
• “” means a single bond or a double bond.