Derivate of benzilidine cyclohexanone, benzilidine cyclopentanone, and benzilidine acetone and their synthesis

Abstract

The invention deals with the derivate of benzelidine having basic formula as follows (I): wherein X can be cyclohexanone, cyclopentanone, or acetone, while Y and Z can be either electron withdrawing, electron donating or steric group. Y may or may not be the same with Z. Methyl, ethyl, methoxy group or halogen were prefered in the experiment. The benzilidine cyclohexanone, benzilidine cyclopentanone, and benzilidine acetone derivates were found to be novel compounds showing anti-bacterial, anti-oxidant, and anti-inflammatory activities that enable them to be used for drug.

1 . Chemical Formula:  
       
         
           
           
               
               
           
         
       
       wherein n between 0-3, R 1 , R 2  and R 3  are methyl, ethyl, methoxy groups, and chloride:  
     
     
         2 . Compound according to  claim 1 , 
 wherein n=3, R 1 =R 3 =methyl and R 2 =OH is 2,6-bis(4-hydroxy-3,5-dimethylbenzilidine)cyclohexanone=HEXAGAMAVUNONE-1=HGV-1.    
     
     
         3 . Compound according to  claim 1 , 
 wherein n=3, R 1 =R 3 =ethyl and R 2 =OH is 2,6-bis(t4-hydroxy-3,5-diethylbenzilidine)cyclohexanone=HEXAGAMAVUNONE-2=HGV-2.    
     
     
         4 . compound according to  claim 1 , 
 wherein n=3, R 1 =R 3 =methoxy and R 2 =OH is 2,6-bis (4-hydroxy-3,5-dimethoxybenzilidine)cyclohexanone=HEXAGAMAVUNONE-5=HGV-5.    
     
     
         5 . Compound according to  claim 1 , 
 wherein n=3, R 1 =R 3 =chloro and R 2 =OH is 2,6-bis(4-hydroxy-3,5-dichlorobenzilidine)cyclohexanone=HEXAGAMAVUNONE-6 HGV-6.    
     
     
         6 . Compound according to  claim 1 , 
 wherein n=2, R 1 =R 3 =methyl and R 2 =OH is 2,5-bis(4-hydroxy-3,5-diethylbenzilidine)cyclopentanone=PENTAGAMAVUNONE-1=PGV-1.    
     
     
         7 . Compound according to  claim 1 , 
 wherein n=2, R 1 =R 3 =ethyl and R 2 =OH is 2,5-bis(4-hydroxy-3,5-dimethylbenzilidine)cyclopentanone=PENTAGAMAVUNONE-2=PGV-2.    
     
     
         8 . Compound according to  claim 1 , 
 wherein n=2, R 1 =R 3 =methoxy and R 2 =OH is 2,5-bis(4-hydroxy-3,5-dimethoxybenzilidine)cyclopentanone=PENTAGAMAVUNONE-5=PGV-5.    
     
     
         9 . Compound according to  claim 1 , 
 wherein n=2, R 1 =R 3 =chloro and R 2 =OH is 2,5-bis(4-hydroxy-3,5-dichlorobenzilidine)cyclopentanone=PENTAGAMAVUNONE-6=PGV-6.    
     
     
         10 . Compound according to  claim 1 , 
 wherein n=2, R 1 =R 3 =methoxy and R 2 =OH is 2,5-bis(4-hydroxy-3,5-methoxybenzilidine)cyclopentanone=PENTAGAMAVUNONE-0=PGV-0.    
     
     
         11 . Compound according to  claim 1 , 
 wherein n=0. R 1 =R 3  chloro and R 2 =OH is 1,5-bis(4-hydroxy-3,5-dichlorophenyl)-1,4-pentadien-3-one=GAMAVUTONE-6=GVT-6.    
     
     
         12 . SAMTISAR Procedure: 1.0 ml of hydroxy benzaldehyde derivatives and 1.0-20.0 mole alkanone were reacted at 0-50° C. with stiring for several hours after which a catalyst was added, stiring continued for 1-3 hours, the mixture was treated with acetic acid and water at several days later, and was filtered, then the solid yield was rinsed with water until free from catalyst, in which recrystallization was performed in ethanol-water, acetone-water mixtures.  
     
     
         13 . Preparation of HGV-1: 4.94 g (0.033 mole) of 3,5-dimethyl-4-hydroxy benzaldehyde and 3,4 ml (0.033 mole) cyclohexanone were stired and heated on a water bath (25-50° C.) for 2 hours and 0.6 ml HCl was added with stiring and said stiring was continued for 2 hours, the mixture was treated with acetic acid-water after 4 days and then was filtered to give solid yield, said solid yield was washed with water until free from acid, then recrystallized in ethanol-water mixture.  
     
     
         14 . Preparation of HGV-2, 5, 6, PGV-1, 2, 5, 6, 0 and GVT-6 as claimed on claim  2 - 11  which were performed similar to that of hexagamavunone with variations in molar quantity, catalyst, reaction time and temperature.  
     
     
         15 . Compounds with anti-inflammatory action are: HGV-1, HGV-2, HGV-6, PGV-1, PGV-2, PGV-5, PGV-6, and PGV-0.  
     
     
         16 . Compounds with anti-oxidative action are HGV-1, HGV-2, HGV-5, PGV-1, PGV-2, PGV-5, PGV-6, and PGV-0.  
     
     
         17 . Compounds with anti-bacterial action are HGV-6, PGV-6, and GVT-6.