Abstract
Suitably substituted para-benzoquinones can show vitamin K-like or antivitamin K activity. The type of activity depends on the nature and position of the substituents.
The benzoquinone analogue of vitamin K1, 2,5,6-trimethyl-3-phytyl-1,4-benzoquinone, shows low vitamin K-like activity and acts as a partial agonist of vitamin K1.
Replacement of the methyl group in the 2-position by a chlorine on bromine atom results in antivitamin K activity, while replacement by a hydrogen atom or methoxy group gives compounds without vitamin K-like or antivitamin K activity.
The methyl groups in the 5- and 6-position are necessary for both vitamin K-like and antivitamin K activity. Replacement of the methyl groups in these positions by a chlorine atom or methoxy group results in loss of either activity.
Replacement of the phytyl side chain in the 3-position by shorter polyisoprenoid side chains in compounds with vitamin K-like or antivitamin K activity also results in loss of either activity.
Footnotes
- Accepted October 5, 1964.
- The Williams & Wilkins Comapny
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