430 



VITAMIN K GROUP 



symmetrical "double molecules" — dicoumarol (10),hydrocoumarol(ll),and 

 tromexan (12) (Fig. 6) — they need not be, for the asymmetric phenylin- 

 danedione (13) and others (14 and 15)^* are also active. Dithiocoumarol (16) 



CHa 



(1) 



O 



OH 



O 

 (2) 







C2H5 

 OH 



O 

 (3) 



O 



(4) 



O O 







(5) 



Q^OCH. 







(6) 



(CH,)3 

 OH 



(7) 



H2 H2 

 -CH CH2 

 H, H2 



/CH3 

 CH2CH 

 OH (CH2)5CH3 



(8) 



H2 



H2 



(CHo)3-CH 9 CH2 



OH 



^C^H C 



H 

 H. H, 



(9) 



OH OH 



(10) 



Fig. 5. 



H OH 



H OH 



(11) 



is weakly hemorrhagic.^* R in compound (17) determines the activity: if R 

 is CH3, the compound is vitamin K-like; if R is an halide or a phenyl 

 derivative, it is an antivitamin K compound. ^^ 



88 P. Meunier, C. Mentzer, and A. Vinet, Helv. Chim. Acta 29, Part 1, 1291 (1946). 

 99 P. Meunier, C. Mentzer, and D. Molho, Compt. rend. acad. sci. (U.R.S.S.) 224, 

 1666 (1947). 



