1246525-60-9

Basic information

• Product Name: SR 1078
• Synonyms: SR 1078;SR1078,N-[4-(2,2,2-Trifluoro-1-hydroxy-1-trifluoroMethyl-ethyl)-phenyl]-4-trifluoroMethyl-benzaMide;N-[4-[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-4-(trifluoromethyl)benzamide;N-[4-[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-4-(trifluoromethyl)benzamide SR1078;N-[4-(1,1,1,3,3,3-Hexafluoro-2-hydroxy-2-propanyl)phenyl]-4-(trifluoromethyl)benzamide
• CAS NO: 1246525-60-9
• Molecular Formula: C₁₇H₁₀F₉NO₂
• Molecular Weight: 431.2524288
• Mol File: 1246525-60-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 169℃
• Boiling Point: 362.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.527±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO, Methanol (Slightly)
• PKA: 9.21±0.15(Predicted)
• CAS DataBase Reference: SR 1078(CAS DataBase Reference)
• NIST Chemistry Reference: SR 1078(1246525-60-9)
• EPA Substance Registry System: SR 1078(1246525-60-9)

Safety Data

• Hazardous Substances Data: 1246525-60-9(Hazardous Substances Data)

Usage

Description

SR 1078 is a selective agonist of RORα and RORγ, which are orphan nuclear receptors that play a role in various cellular processes, including cell differentiation, metabolism, and immune responses. As a small molecule, SR 1078 has the ability to stimulate ROR transcriptional activity, making it a valuable tool for studying the functions and mechanisms of ROR receptors.

Uses

Used in Pharmaceutical Research:
SR 1078 is used as a research tool for investigating the role of RORα and RORγ receptors in various biological processes. By selectively activating these receptors, researchers can gain insights into their functions and potential therapeutic applications.
Used in Drug Discovery:
SR 1078 is used as a lead compound in the development of new drugs targeting RORα and RORγ receptors. Its ability to stimulate ROR transcriptional activity makes it a promising candidate for the treatment of diseases associated with these receptors, such as autoimmune disorders, metabolic diseases, and cancer.
Used in Cell Differentiation Studies:
SR 1078 is used as an inducer of cell differentiation in various cell types, including stem cells and immune cells. By activating RORα and RORγ receptors, SR 1078 can promote the differentiation of these cells into specific lineages, providing valuable information on the molecular mechanisms underlying cell fate decisions.
Used in Metabolic Research:
SR 1078 is used as a modulator of metabolic pathways in cells, particularly those involving RORα and RORγ receptors. Its ability to stimulate ROR transcriptional activity can help researchers understand the role of these receptors in regulating glucose and lipid metabolism, as well as their potential as targets for the treatment of metabolic disorders.
Used in Immunology Research:
SR 1078 is used as an immunomodulatory agent in the study of immune cell function and the regulation of immune responses. By activating RORα and RORγ receptors, SR 1078 can influence the differentiation and function of various immune cells, providing insights into the role of these receptors in immune system regulation and the development of novel immunotherapies.

Biological Activity

sr1078 is an agonist of retinoic acid receptor-related orphan receptor (ror) rorα and rorγ with ic50 values of both 1-3 μm [1].rorα and rorγ are two members of nuclear receptor superfamily, which possesses a highly conserved dna-binding and a ligand-binding domain. these two receptors are considered to play important roles in the regulation of metabolism and the function of immune system [1].sr1078 is a selective rorα and rorγ agonist, which activate rorα and rorγ directed transcription via inducing conformational changes [1].sr1078 selectively targets on rorα and rorγ as an agonist but not on lxr and fxr [1]. it was shown that sr1078 was able to stimulate ror activity and subsequent ror-directed mrna expression. when hepg2 cells were treated with sr1078 for 24h, the ror directed reporter gene fg21 mrna level was increased by 3-fold, while another reporter gene g6pase was increased by 2-fold [1].in mouse model, i.p. injection of 10 mg/kg sr1078 for 1 hr resulted in 3.6 μm plasma concentration., and after 8 hr the concentration still sustained at 800 nm. i.p. injection of 10 mg/kg sr1078 for 2 hr resulted in significantly increased level of mrna of reporter gene g6pase and fg21 [1].

references

[1] wang y et al. , identification of a synthetic agonist for the orphan nuclear receptors rorα and rorγ, sr1078. acs chem biol., 2010, 5(11): 1029-1034.

Synthetic route

2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (722-92-9) + 4-trifluoromethyl-phenyl acetyl chloride (329-15-7) → SR1078 (1246525-60-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 8h; Inert atmosphere;	71%
With triethylamine In 1,4-dioxane at 23℃;

Upstream product

• 722-92-9 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 

Relevant articles and documents

Structure-based design of substituted hexafluoroisopropanol- arylsulfonamides as modulators of RORc

The structure-activity relationships of T0901317 analogs were explored as RORc inverse agonists using the principles of property- and structure-based drug design. An X-ray co-crystal structure of T0901317 and RORc was obtained and provided molecular insight into why T0901317 functioned as an inverse agonist of RORc; whereas, the same ligand functioned as an agonist of FXR, LXR, and PXR. The structural data was also used to design inhibitors with improved RORc biochemical and cellular activities. The improved inhibitors possessed enhanced selectivity profiles (rationalized using the X-ray crystallographic data) against other nuclear receptors.