328956-38-3 Usage
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 academic research and scientific papers
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.
Discovery of 6-N,N-Bis(2,2,2-trifluoroethyl)amino-4- trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator
Van Oeveren, Arjan,Motamedi, Mehrnouch,Mani, Neelakandha S.,Marschke, Keith B.,López, Francisco J.,Schrader, William T.,Negro-Vilar, Andrés,Zhi, Lin
, p. 6143 - 6146 (2007/10/03)
The androgen receptor is a member of the extended family of nuclear receptors and is widely distributed throughout the body. Androgen therapy is used to compensate for low levels of the natural hormones testosterone (T) and dihydrotestosterone and consist
