1939-27-1 Usage
Description
3'-Trifluoromethylisobutyranilide, also known as 2-Methyl-N-[3-(trifluoromethyl)phenyl]propanamide, is a chemical compound that serves as a crucial intermediate in the synthesis of various pharmaceuticals. It is characterized by its unique molecular structure, which includes a trifluoromethyl group attached to a phenyl ring, and an isobutyranilide side chain. 3'-Trifluoromethylisobutyranilide is known for its potential applications in the development of medications, particularly in the field of oncology.
Uses
Used in Pharmaceutical Synthesis:
3'-Trifluoromethylisobutyranilide is used as a key reagent for the synthesis of Flutamide (F598850), an oral nonsteroidal antiandrogen. Flutamide is primarily utilized in the treatment of patients with prostate cancer. The compound's unique structure allows for the development of medications that can effectively target androgen receptors, thereby inhibiting the growth of cancer cells.
Used in Oncology:
In the field of oncology, 3'-Trifluoromethylisobutyranilide plays a significant role in the development of antiandrogen drugs like Flutamide. These drugs are specifically designed to treat prostate cancer by blocking the action of androgens, which are hormones that promote the growth of prostate cancer cells. By inhibiting the androgen receptors, Flutamide can help slow down or stop the progression of the disease, providing a valuable treatment option for patients.
Used in Drug Development:
3'-Trifluoromethylisobutyranilide is also used in the research and development of new drugs with potential applications in various therapeutic areas. Its unique chemical properties make it an attractive candidate for the design and synthesis of novel compounds with improved pharmacological profiles. This can lead to the discovery of more effective and safer medications for a wide range of diseases, including cancer and other conditions.
Check Digit Verification of cas no
The CAS Registry Mumber 1939-27-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,3 and 9 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1939-27:
(6*1)+(5*9)+(4*3)+(3*9)+(2*2)+(1*7)=101
101 % 10 = 1
So 1939-27-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H12F3NO/c1-7(2)10(16)15-9-5-3-4-8(6-9)11(12,13)14/h3-7H,1-2H3,(H,15,16)
1939-27-1Relevant articles and documents
Comparison of photoreactions of flutamide in acetonitrile and 2-propanol solvents in the absence of cage-forming compounds
Watanabe, Yurie,Fukuyoshi, Shuichi,Oda, Akifumi
, p. 55 - 61 (2015)
Flutamide(2-methyl-N-[4-nitro-3-(trifluoromethylphenyl)]propanamide) is a widely used anti-cancer drug. It has been reported that photodermatosis is occasionally induced when an individual taking flutamide is exposed to sunlight. In this study, we found that flutamide undergoes different photoreactions in two different solvents: acetonitrile and 2-propanol. The photo-induced nitro-nitrite rearrangement was the predominant reaction when a flutamide solution in acetonitrile was irradiated with UV light, and phenoxy radicals and nitrogen monoxide were generated. The nitrogen monoxide recombined with the phenoxy radical at the ortho position and was oxidized by the oxygen dissolved in the acetonitrile. The final product was o-nitrophenol derivative. However, the photoreduction of the nitro group followed by solvolysis of the trifluoromethyl group was observed when a flutamide solution in 2-propanol was irradiated with UV light. The three fluorine atoms in the trifluoromethyl group were eliminated by being nucleophilically attacked by a solvent molecule, resulting in an ester bond with 2-propanol being formed.
Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water
Tan, Bryan Yong-Hao,Teo, Yong-Chua
supporting information, p. 1697 - 1701 (2015/07/20)
A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C2O4)·2H2O/N,N′-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.
A novel method for synthesis of flutamide on the bench-scale
Ghaffarzadeh, Mohammad,Rahbar, Sahar
, p. 200 - 201 (2014/05/06)
Flutamide has been synthesised conveniently in high yields and by an economically beneficial method. Benzotrifluoride was first nitrated and the product was reduced and acylated in one pot in the presence of iron powder and isobutyric acid to produce 3-trifluoroisobutyranilide. Finally, flutamide was produced by further nitration.
