Dat1

Abstract

A synthetic diaminoketothiazole, its process of preparation and its use as a microtubule inhibitor, a probe for tubulin-microtubule system and a cytotoxic agent. Diaminoketothiazole of the formula (I) wherein Ar is 4-OMe-C 6 H 5 , Ar′ is C 6 H 5 .

1 - 10 . (canceled) 
     
     
         11 . Diaminoketothiazole of the formula: 
       
         
           
           
               
               
           
         
       
       wherein Ar is 4-OMe-C 6 H 5  and 
       Ar′ is C 6 H 5 . 
     
     
         12 . A process for preparing diaminoketothiazole (DAT1), comprising:
 reacting aminomethylpolystyrene beads and 1-[N-(arylthiocarbamoyl) amidino]-3,5-dimethylpyrazole to produce N—(N-arylthiocarbamoyl)-N-guanidinomethyl polystyrene (2);   reacting said N—(N-arylthiocarbamoyl)-N-guanidinomethyl polystyrene with alphahaloketones in the presence of a base which produces an acyclic S-alkyl intermediate derivative (3);   subjecting the acyclic S-alkyl intermediate to the step of cyclisation to obtain the intermediate cyclic thiazoline (4);   subjecting the cyclic thiazoline intermediate to the step of eliminative aromatization to produce diaminoketothiazole in a solution;   filtering said solution to remove impurities and then isolating 5-aroyl-4-amino-2-arylaminothiazoles from the solution by precipitation.   
     
     
         13 . The process as claimed in  claim 12 , wherein said α-haloketones is α-bromoketone. 
     
     
         14 . The process as claimed in  claim 13 , wherein said step of precipitation is done by using ice-cold water. 
     
     
         15 . The diaminoketothiazole (DAT1) as claimed in  claim 11 , wherein said DAT1 is a microtubule inhibitor and a cytotoxic agent. 
     
     
         16 . The DAT1 as claimed in  claim 11 , wherein said DAT1 distorts microtubules in HeLa cells as well as inhibits the in vitro assembly of microtubular proteins. 
     
     
         17 . The DAT1 as claimed in  claim 11 , wherein said DAT1 arrests mitosis in diseases where unwanted cell division is involved. 
     
     
         18 . The DAT1 as claimed in  claim 11 , wherein said DAT1 is capable of shifting the tubulin-microtubule equilibrium in the cell by inhibiting microtubule polymerization. 
     
     
         19 . The DAT1 as claimed in  claim 11 , wherein said DAT1 binds to tubulin with high affinity. 
     
     
         20 . The DAT1 as claimed in  claim 19 , wherein said DAT1 binds to tubulin with exhibition of fluorescence.