Synthesis of Sodium Narcistatin and Related Compounds

Abstract

The present invention involves use of the compounds narciclasine (2a) and 7-deoxy-narciclasine (2c), which are obtained via isolation from the medicinal plant species Narcissus (Amaryllidaceae), as precursors in a novel synthesis method in which each of these compounds are selectively hydrogenated to produce trans-dihydronarciclasine (1a) and 7-deoxy-trans-dihydronarciclasine (1c). Also described herein is a novel synthesis method for producing sodium narcistatin (11) from narciclasine (2a). Further described herein are certain novel 3,4-cyclic phosphate prodrugs, including sodium-7-deoxynarcistatin (8), sodium-7-deoxy-transdihydronarcistatin (9), and sodium transdihydronarcistatin (10).

1 - 10 . (canceled) 
   
   
       11 . A method of inhibiting the growth of a cancer cell comprising contacting said cancer cell with a compound having the following structure: 
     
       
         
         
             
             
         
       
     
   
   
       12 . The method of  claim 11 , wherein said cell is selected from the group consisting of a leukemia cell, a pancreatic cancer cell, a breast cancer cell, a central nervous system cancer cell, a lung cancer cell, a colon cancer cell and a prostate cancer cell. 
   
   
       13 . A method of inhibiting the growth of a cancer cell comprising contacting said cancer cell with a compound having the following structure: 
     
       
         
         
             
             
         
       
     
   
   
       14 . The method of  claim 13 , wherein said cell is selected from the group consisting of a leukemia cell, a pancreatic cancer cell, a breast cancer cell, a central nervous system cancer cell, a lung cancer cell, a colon cancer cell and a prostate cancer cell. 
   
   
       15 . A method of inhibiting the growth of a cancer cell comprising contacting said cancer cell with a compound having the following structure: 
     
       
         
         
             
             
         
       
     
   
   
       16 . The method of  claim 15 , wherein said cell is selected from the group consisting of a leukemia cell, a pancreatic cancer cell, a breast cancer cell, a central nervous system cancer cell, a lung cancer cell, a colon cancer cell and a prostate cancer cell.