Linked diaryl compounds with anticancer properties and methods of using the same

Abstract

Provided are compositions comprising linked diaryl compounds that possess anticancer properties. Methods of use are also disclosed herein. The method comprises administering an effective amount of a compound described herein to an individual in need thereof.

1 . A compound having the formula: 
       
         
           
           
               
               
           
         
       
       wherein
 W is selected from the group consisting of —R 1 , —OR 1 , —N(R 1 ) 2 , —NO 2 , -halogen, 
 
       
         
           
           
               
               
           
         
          wherein
 E is selected from the group consisting of oxygen atom, sulfur atom, —N(R 1 )—, and —N(OR 1 )—; 
 X is —N—, or —C(R 1 )—; 
 Y is selected from the group consisting of —R 1 , -ER 1 , —X(R 1 ) 2 , and -halogen; 
 n is 0-6, and 
 R 1  is selected from the group consisting of H, substituted or unsubstituted C 1 -C 14  alkyl, substituted or unsubstituted C 1 -C 14  heteroalkyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 1 -C 14  alkenyl, substituted or unsubstituted C 1 -C 14  heteroalkenyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 1 -C 14  alkynyl, substituted or unsubstituted C 1 -C 14  heteroalkynyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 5 -C 14  aryl, halo, heteroaryl having 5-14 ring atoms, wherein 1-8 of the ring atoms are independently O, N, S, P, or B, 
 
       
       
         
           
           
               
               
           
         
          wherein
 Y 1  is selected from the group consisting of —OR 1 , —NR 1 , —SR 1 , and —R 1 ; 
 
         L is selected from the group consisting of direct covalent bond, —O—, —NH—, —O—(CH 2 ) m —O—, —NH—(CH 2 ) m —NH—, 
       
       
         
           
           
               
               
           
         
          wherein
 m is 2-6; 
 
         Q is selected from the group consisting of —OH, —SH, —NR 1 , 
       
       
         
           
           
               
               
           
         
          wherein
 A is selected from the group consisting of direct covalent bond, —SO 2 —NH—, —NH—; and 
 Z is selected from the group consisting of —S—, —O—, -ER 1 -, —CH, —N—, —NH—, —N + (R 1 )—, and —N(R 1 ). 
 
       
     
     
         2 . (canceled) 
     
     
         3 . The compound of  claim 5 , wherein the compound has the following formula: 
       
         
           
           
               
               
           
         
       
       wherein
 W is selected from the group consisting of —R 1 , —OR 1 , —N(R 1 ) 2 , —NO 2 , -halogen, 
 
       
         
           
           
               
               
           
         
          wherein
 E is selected from the group consisting of oxygen atom, sulfur atom, —N(R 1 )—, and —N(OR 1 )—; 
 X is —N—, or —C(R 1 )—; 
 Y is selected from the group consisting of —R 1 , -ER 1 , —X(R 1 ) 2 , and -halogen; and 
 R 1  is selected from the group consisting of H, substituted or unsubstituted C 1 -C 14  alkyl, substituted or unsubstituted C 1 -C 14  heteroalkyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 1 -C 14  alkenyl, substituted or unsubstituted C 1 -C 14  heteroalkenyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 1 -C 14  alkynyl, substituted or unsubstituted C 1 -C 14  heteroalkynyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 5 -C 14  aryl, halo, heteroaryl having 5-14 ring atoms, wherein 1-8 of the ring atoms are independently O, N, S, P, or B, 
 
       
       
         
           
           
               
               
           
         
          wherein
 n is 0-6; and
 Y 1  is selected from the group consisting of —OR 1 , —NR 1 , —SR 1 , and —R 1 . 
 
 
       
     
     
         4 . The compound of  claim 3 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         5 . The compound of  claim 1 , wherein the compound has the following formula: 
       
         
           
           
               
               
           
         
       
       wherein
 Q is selected from the group consisting of —OH, —SH, —NR 1 , 
 
       
         
           
           
               
               
           
         
          wherein
 E is selected from the group consisting of oxygen atom, sulfur atom, —N(R 1 )—, and —N(OR 1 )—; 
 R 1  is selected from the group consisting of H, substituted or unsubstituted C 1 -C 14  alkyl, substituted or unsubstituted C 1 -C 14  heteroalkyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 1 -C 14  alkenyl, substituted or unsubstituted C 1 -C 14  heteroalkenyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 1 -C 14  alkynyl, substituted or unsubstituted C 1 -C 14  heteroalkynyl, wherein 1-7 of the chain atoms are independently O, N, S, P, or B, substituted or unsubstituted C 5 -C 14  aryl, halo, heteroaryl having 5-14 ring atoms, wherein 1-8 of the ring atoms are independently O, N, S, P, or B, 
 
       
       
         
           
           
               
               
           
         
          wherein
 Y 1  is selected from the group consisting of —OR 1 , —NR 1 , —SR 1 , and —R 1 ; 
 A is selected from the group consisting of direct covalent bond, —SO 2 —NH—, —NH—; and 
 Z is selected from the group consisting of —S—, —O—, -ER 1 -, —CH, —N—, —NH—, —N + (R 1 )—, and —N(R 1 )—; 
 
         W is selected from the group consisting of —R 1 , —OR 1 , —N(R 1 ) 2 , —NO 2 , -halogen, 
       
       
         
           
           
               
               
           
         
          wherein
 X is —N—, or —C(R 1 )—; and 
 Y is selected from the group consisting of —R 1 , -ER 1 , —X(R 1 ) 2 , and -halogen. 
 
       
     
     
         6 . The compound of  claim 5 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         7 - 19 . (canceled) 
     
     
         20 . A method for inhibiting growth of cancer cells comprising introducing into the cancer cells a compound of  claim 1 , wherein the cancer cells are selected from ovarian, prostate and breast cancer cells. 
     
     
         21 . The method of  claim 20  wherein, subsequent to the introducing, a complex of the compound and a polynucleotide is formed in the cancer cells. 
     
     
         22 . The method of  claim 20  wherein, subsequent to the introducing, telomerase activity in the cancer cells is inhibited. 
     
     
         23 . (canceled) 
     
     
         24 . The method of  claim 20 , wherein the cancer cells are in an individual diagnosed with or suspected of having a cancer comprising the cancer cells.