SR9009

Base Information

• Chemical Name: SR9009
• CAS No.: 1379686-30-2
• Molecular Formula: C20H24ClN3O4S
• Molecular Weight: 437.947
• Mol file: 1379686-30-2.mol

Synonyms:SR9009;3-[[[(4-Chlorophenyl)methyl][(5-nitro-2-thienyl)methyl]amino]methyl]-1-pyrrolidinecarboxylic acid ethyl ester

Chemical Property of SR9009

Chemical Property:

• Boiling Point: 547.2±45.0 °C(Predicted)
• PKA: 6.12±0.50(Predicted)
• PSA: 106.84000
• Density: 1.327±0.06 g/cm3(Predicted)
• LogP: 5.25140
• Storage Temp.: -20°
• Solubility.: Soluble in DMSO (greater than 25 mg/ml) or in Ethanol (up to 20 mg/ml).

Purity/Quality:

99% ^*data from raw suppliers

SR9009 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: SR-9009 is an agonist at nuclear receptor Rev-ErbA. Greatly diminishes VILI-induced lung edema, inflammatory cell infiltration and TNFα production in a rat lung injury model. SR-9009 suppresses atherosclerosis in a mouse model. Specifically lethal to cancer cells and oncogene-induced senescent cells with no effect on the viability of normal cells or tissues. Disrupts pain associated with osteoarthritis by reducing BMAL1 expression in bmal1f/fNav1.8CreERT mice.
• Uses: SR 9009 is a synthetic REV-ERB agonist that regulates circadian behavior and metabolism; has potential use in the treatment of sleep disorders and metabolic diseases. It is a lead compound for a new class of cancer drugs associated with the body’s circadian clock.

Technology Process of SR9009

There total 5 articles about SR9009 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) → SR9009 (1379686-30-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane

2: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane

3: trifluoroacetic acid / dichloromethane

4: triethylamine / dichloromethane

With sodium tris(acetoxy)borohydride; acetic acid; triethylamine; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2012.04.126

Reference yield:

N-(4-chlorobenzyl)-1-(5-nitrothiophen-2-yl)methanamine (1384516-10-2) → SR9009 (1379686-30-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane

2: trifluoroacetic acid / dichloromethane

3: triethylamine / dichloromethane

With sodium tris(acetoxy)borohydride; acetic acid; triethylamine; trifluoroacetic acid; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.bmcl.2012.04.126

Reference yield:

tert-butyl 3-(((4-chlorobenzyl)((5-nitrothiophen-2-yl)methyl)amino)methyl)pyrrolidine-1-carboxylate (1384516-20-4) → SR9009 (1379686-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane

2: triethylamine / dichloromethane

With triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2012.04.126

upstream raw materials:

5-nitro-2-thiophenecarboxaldehyde

N-(4-chlorobenzyl)-1-(5-nitrothiophen-2-yl)methanamine

tert-butyl 3-(((4-chlorobenzyl)((5-nitrothiophen-2-yl)methyl)amino)methyl)pyrrolidine-1-carboxylate

chloroformic acid ethyl ester

Refernces