Uses
Phenylamidone drugs are mainly used to treat amoebic dysentery and bacillary dysentery. Most existing synthetic methods involve nitrification, reduction, and hydrolysis of o-acetamipridanisole to produce 2,5-diaminoanisole sulfate, which is then reacted with glycerol and concentrated sulfuric acid in the presence of iodine and potassium iodide under heating to cyclize and obtain 6-methoxy-4,7-diaphenanthrene, which is then further oxidized to obtain the finished product.
Chemical Properties
Orange-red crystalline powder. Melting point 295°C. Slightly soluble in water, insoluble in ethanol and chloroform. Odorless, slightly bitter.
Originator
Phanquinone ,Yick-Vic Chemicals and
Definition
ChEBI: An orthoquinone that is the 5,6-diketo derivative of 4,7-phenanthroline.
Manufacturing Process
2 parts of 6-methoxy-4:7-phenanthroline are mixed with 10 parts by volume of concentrated sulfuric acid and while cooling with a mixture of ice and sodium chloride, with 6 parts by volume of fuming nitric acid (density = 1.51), and the whole is heated for 2 h at 120°C. The reaction solution is poured on to ice, its pH value is adjusted to 7 by means of a 10 N solution of caustic soda, after standing for 2 h the whole is filtered with suction to remove the precipitate which separates, and the latter is washed with hot water. After recrystallising the product from methyl alcohol and drying it at 100°C under 0.1 mm pressure, there are obtained 1.8 parts (i.e. 90 % of the calculated yield) of 4:7-phenanthroline-5:6-quinone in the form of pale yellow crystals melting at 295°C.
Therapeutic Function
Antiamebic
Safety Profile
Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Purification Methods
The dione crystallises from MeOH. The mono-oxime forms yellow crystals from MeOH with m 250o(dec), the di-oxime forms yellow crystals from MeOH with m 300o(dec) and the mono-semihydrazone forms yellow crystals from MeOH with m 195o(dec). [Druey & Schmidt Helv Chim Acta 33 1080 1950, Beilstein 24 III/IV 1741.]
