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393-09-9

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Development of nonsteroidal antiandrogens: 4-Nitro-3-trifluoro-methyldiphenylamines
For the development of new nonsteroidal antiandrogens a series of 4-nitro-3-trifluoromethyldiphenylamines was synthesized and compounds were tested for their affinities to steroid hormone receptors and for antiandrogenic activities. These compounds were synthesized by reacting 4-nitro-3-trifluoromethylphenylsulfocyanamide-sodium (4) with the corresponding aromatic amines to give the N-(4-nitro-3-trifluoromethylphenylsulfonyl)-N'-phenylguanidines. The crude products were then converted to the desired diphenylamines by Smiles rearrangement and hydrolysis. 2-Hydroxy-4'-nitro-3'-trifluoromethyldiphenylamine (13), which shows a relative binding affinity (RBA) to the androgen receptor (AR) of 6.5% of that of testosterone, exerts a higher affinity than hydroxyflutamide (RBA = 4.5). Shift of the hydroxy-function to position 3 or 4 as well as N-methylation caused a decrease in AR-affinity. Compounds exerting AR-affinity were tested for antiandrogenic activity. Compound 13 showed the best antiandrogenic effect, though less than the well-known antiandrogen flutamide.
Humm,Schneider
p. 83 - 87
(2007/10/02)

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Chemical Properties

Appearance/Colour :clear yellow liquid after melting
Melting Point: 23 ºC
Boiling Point: 198-199 ºC
Flash Point:88 ºC
Density: 1.497
Solubility:Soluble in chloroform and methanol.
Storage Temp.:Refrigerator
Vapor Pressure: 0.506mmHg at 25°C
Refractive Index: n20/D 1.46(lit.)
BRN: 3304470
PSA: 45.82000
LogP: 3.27590

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