SR9009

  • CasNo:1379686-30-2
  • Molecular Formula:C20H24ClN3O4S
  • Purity:
  • Molecular Weight:437.947
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Product Details

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  • Molecular Formula:C20H24ClN3O4S
  • Molecular Weight:437.947
  • 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 

SR9009 (Cas 1379686-30-2) Usage

Description

SR9009, a putative ligand, has been reported to elicit a range of beneficial effects in healthy as well as diseased animal models and cell systems. 

Uses

SR9009 reduces the adverse NLRP3 inflammasome and genetic loss of REV-ERB repressor activity. SR9009 which acts as a REV-ERBs-specific agonist exhibits potent in vivo activity on metabolism and tumor cell viability.

IUPAC Name: ethyl 3-[[(4-chlorophenyl)methyl-[(5-nitrothiophen-2-yl)methyl]amino]methyl]pyrrolidine-1-carboxylate  
Isomeric SMILES: CCOC(=O)N1CCC(C1)CN(CC2=CC=C(C=C2)Cl)CC3=CC=C(S3)[N+](=O)[O-]  
InChIKey: MMJJNHOIVCGAAP-UHFFFAOYSA-N  
InChI: InChI=1S/C20H24ClN3O4S/c1-2-28-20(25)23-10-9-16(13-23)12-22(11-15-3-5-17(21)6-4-15)14-18-7-8-19(29-18)24(26)27/h3-8,16H,2,9-14H2,1H3  

1379686-30-2 Relevant articles

SR9009 inhibits lethal prostate cancer subtype 1 by regulating the LXRα/FOXM1 pathway independently of REV-ERBs

Hang Xu, Jiapeng Zhang, Xiaonan Zheng, Ping Tan, Xingyu Xiong, Xianyanling Yi, Yang Yang, Yan Wang, Dazhou Liao, Hong Li, Qiang Wei, Jianzhong Ai & Lu Yang

, Cell Death & Disease volume 13, Article number: 949 (2022)

Although most SR9009-related studies have demonstrated that the therapeutic effect of SR9009 occurs via REV-ERBs, several reports have also revealed that SR9009 might also work in a REV-ERB-independent manner.

SR9009 administered for one day after myocardial ischemia-reperfusion prevents heart failure in mice by targeting the cardiac inflammasome

Cristine J. Reitz, Faisal J. Alibhai, Tarak N. Khatua, Mina Rasouli, Byram W. Bridle, Thomas P. Burris & Tami A. Martino

, Communications Biology volume 2, Article number: 353 (2019)

To investigate the early mechanisms responsible, we first showed that SR9009 treatment downregulates Rev-Erb in the heart. We found that SR9009 treatment of normal mice decreased (p < 0.05) Rev-Erbα and Rev-Erbβ mRNA  and protein  expression in the heart, as compared with vehicle-treated controls.

1379686-30-2 Process route

5-nitro-2-thiophenecarboxaldehyde
4521-33-9

5-nitro-2-thiophenecarboxaldehyde

SR<sub>9009</sub>
1379686-30-2

SR9009

Conditions
Conditions Yield
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;
 
N-(4-chlorobenzyl)-1-(5-nitrothiophen-2-yl)methanamine
1384516-10-2

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

SR<sub>9009</sub>
1379686-30-2

SR9009

Conditions
Conditions Yield
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;
 

1379686-30-2 Upstream products

  • 4521-33-9
    4521-33-9

    5-nitro-2-thiophenecarboxaldehyde

  • 1384516-10-2
    1384516-10-2

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

  • 1384516-20-4
    1384516-20-4

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

  • 541-41-3
    541-41-3

    chloroformic acid ethyl ester