328956-38-3 Usage
Description
6-Nitro-4-(trifluoromethyl)quinolin-2(1H)-one is a chemical compound that serves as an intermediate in the synthesis of various pharmaceuticals. It is characterized by its quinolinone structure with a nitro group at the 6th position and a trifluoromethyl group at the 4th position.
Uses
Used in Pharmaceutical Industry:
6-Nitro-4-(trifluoromethyl)quinolin-2(1H)-one is used as an intermediate in the synthesis of LGD-2226 (L397615), an orally active potent and selective androgen receptor modulator. 6-nitro-4-(trifluoromethyl)quinolin-2(1H)-one is utilized in the treatment of muscle wasting and osteoporosis, as it has been shown to have an anabolic effect on muscle and bone tissue.
Synthesis
6-Nitro-4-trifluoromethylquinolin-2(1H)-one is obtained by nitration with 4-Trifluoromethylquinolin-2(1H)-one.Experimental Procedure：A milky suspension of 33.0 g 4-Trifluoromethylquinolin-2(1H)-one in 200 mL H2SO4 was cooled in an ice-salt bath to -5°C. 14.3 g
70% HNO3 was added dropwise, keeping the internal temperature below 7°C. After addition
was complete, the mixture was stirred at 0-10°C for 1 h and then after removal of the ice bath
the temperature raised to room temperature within the next hours. The yellow solution was then
poured onto 600 g crushed ice and kept standing/stirring for the next 12 h. The resulting two
phases were separated and the organic phase equals a yellow slurry, which was filtered by
suction. The resulting solid was washed with water and dried under vacuum. After
crystallization of 20 g crude product in 1 L ethanol a nearly colorless solid (6-Nitro-4-trifluoromethylquinolin-2(1H)-one) (43%) was
obtained.
Check Digit Verification of cas no
The CAS Registry Mumber 328956-38-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,2,8,9,5 and 6 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 328956-38:
(8*3)+(7*2)+(6*8)+(5*9)+(4*5)+(3*6)+(2*3)+(1*8)=183
183 % 10 = 3
So 328956-38-3 is a valid CAS Registry Number.
328956-38-3Relevant articles and documents
Novel selective androgen receptor modulators: SAR studies on 6-bisalkylamino-2-quinolinones
van Oeveren, Arjan,Motamedi, Mehrnoush,Martinborough, Esther,Zhao, Shuo,Shen, Yixing,West, Sarah,Chang, William,Kallel, Adam,Marschke, Keith B.,Lopez, Francisco J.,Negro-Vilar, Andres,Zhi, Lin
, p. 1527 - 1531 (2007/10/03)
A series of selective androgen receptor modulators (SARMs) with a wide spectrum of receptor modulating activities was developed based on optimization of the 4-substituted 6-bisalkylamino-2-quinolinones (3). Significance of the trifluoromethyl group on the side chains and its interactions with amino acid residues within the androgen receptor (AR) ligand binding domain are discussed. A representative analog (9) was tested orally in a rodent model of hypogonadism and demonstrated desirable tissue selectivity.
