Substituted berbines and their synthesis

1. A compound of Formula (V-1):

wherein:

R 1 R 2 , R 3 , and R 4 independently are hydrogen, halogen, OR 15 , NR 15 N 16 , nitro, cyano, thiol, hydrocarbyl, substituted hydrocarbyl, or together R 2 and R 3 along with the ring carbons to which they are attached form a ring comprising {—}O(CH 2 ) n O{—};

R 5 , R 6 , R 7 , and R 8 independently are hydrogen, halogen, OR 15 , NR 15 N 16 , nitro, cyano, thiol, hydrocarbyl, substituted hydrocarbyl, or together R 6 and R 7 along with the ring carbons to which they are attached form a ring comprising {—}O(CH 2 ) n O{—}; provided that at least two of R 6 , R 7 , and R 8 are other than methoxy;

R 9 , R 10 , R 11 , and R 12 independently are hydrogen, hydrocarbyl, or substituted hydrocarbyl;

R 21 , R 22 , R 23 , R 24 , and R 25 independently are hydrogen, halogen, OR 15 , NR 15 N 16 , nitro, cyano, thiol, hydrocarbyl, or substituted hydrocarbyl;

R 15 and R 16 independently are hydrogen, hydrocarbyl, or substituted hydrocarbyl;

m is an integer of 0;

n is an integer from 1 to 3; and

the dashed lines represent optional double bonds.

2. The compound of claim 1 , wherein each of R 1 , R 4 , R 9 , R 10 , R 11 , and R 12 is hydrogen; R 2 and R 3 independently are hydrogen, halogen, hydroxy, alkyoxy, alkyl or together R 2 and R 3 form {—}O—CH 2 —O{—}; R 5 and R 8 independently are hydrogen, halogen, hydroxy, alkoxy, or alkyl; R 6 and R 7 independently are hydrogen, halogen, hydroxy, alkoxy, alkyl, aryloxy, substituted aryloxy, nitro, amino, amine, or amide; and R 21 , R 22 , R 23 , R 24 , and R 25 independently are hydrogen, halogen, hydroxy, alkoxy, alkyl, nitro, amino, or amine.

3. The compound of claim 1 , wherein the compound has Formula (V-1a):

wherein:

R 2 is hydroxy or alkyoxy and R 3 is hydrogen, or together R 2 and R 3 form {—}O—CH 2 —O{—};

R 5 and R 8 independently are hydrogen, halogen, hydroxy, alkoxy, or alkyl;

R 6 and R 7 independently hydrogen, halogen, hydroxy, alkyoxy, alkyl aryloxy, substituted aryloxy, nitro, amino, amine, or amide;

R 20 is hydrogen, halogen, hydroxy, alkoxy, alkyl, nitro, amino, or amine; and

m is 0.

4. The compound of claim 1 , wherein the compound has Formula (V-1b):

wherein:

R 2 is hydroxy or alkyoxy and R 3 is hydrogen, or together R 2 and R 3 form {—}O—CH 2 —O{—};

R 5 and R 8 independently are hydrogen, halogen, hydroxy, alkoxy, or alkyl;

R 6 and R 7 independently hydrogen, halogen, hydroxy, alkyoxy, alkyl aryloxy, substituted aryloxy, nitro, amino, amine, or amide;

R 20 is hydrogen, halogen, hydroxy, alkoxy, alkyl, nitro, amino, or amine; and

m is 0.

5. The compound of claim 1 , wherein the compound is chosen from the following compounds:

wherein:

R 2 is hydroxy or alkyoxy and R 3 is hydrogen, or together R 2 and R 3 form {—}O—CH 2 —O{—}

R 14 is alkyl or substituted alkyl.

R 15 is hydrogen or C 1 -C 6 alkyl;

X is halogen; and

Y and Z independently are hydrogen, halogen, hydroxy, alkoxy, alkyl, nitro, amino, or amine.