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96187-53-0,MFCD00866437
Catalog No.:AA006SCA

96187-53-0 | 6-Fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid

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1mg
≥98%
in stock  
$46.00   $32.00
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25mg
in stock  
$122.00   $85.00
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50mg
96%
in stock  
$181.00   $127.00
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100mg
96%
in stock  
$218.00   $153.00
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250mg
96%
in stock  
$435.00   $305.00
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1g
96%
in stock  
$1,074.00   $752.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA006SCA
Chemical Name:
6-Fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid
CAS Number:
96187-53-0
Molecular Formula:
C23H15F2NO2
Molecular Weight:
375.3675
MDL Number:
MFCD00866437
SMILES:
Fc1ccc2c(c1)c(C(=O)O)c(c(n2)c1ccc(cc1)c1ccccc1F)C
Properties
Properties
 
BP:
550.9°C at 760 mmHg  
Form:
Solid  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
551  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
5.6  

Downstream Synthesis Route
443-69-6    60-29-7    37989-92-7   
brequinar 

[1]Patent:US4680299,1987,A

[2]Patent:US4861783,1989,A

443-69-6    37989-92-7   
brequinar 

[1]Chemistry-AEuropeanJournal,2017,vol.23,p.13875-13878

[2]Cell,2016,vol.167,p.171-15,186

[3]Patent:WO2017/37022,2017,A1.Locationinpatent:Page/Pagecolumn54;55

96187-53-0   
CASUnavailable 

[1]CurrentPatentAssignee:BROADINSTITUTE;MASSGENERALBRIGHAMINC;BAYERAG;HARVARDUNIVERSITY-WO2017/37022,2017,A1Locationinpatent:Page/Pagecolumn54;55

[2]Sykes,DavidB.;Kfoury,YoumnaS.;Mercier,FrançoisE.;Wawer,MathiasJ.;Law,JasonM.;Haynes,MarkK.;Lewis,TimothyA.;Schajnovitz,Amir;Jain,Esha;Lee,Dongjun;Meyer,Hanna;Pierce,KerryA.;Tolliday,NicolaJ.;Waller,Anna;Ferrara,StevenJ.;Eheim,AshleyL.;Stoeckigt,Detlef;Maxcy,KatrinaL.;Cobert,JulienM.;Bachand,Jacqueline;Szekely,BrianA.;Mukherjee,Siddhartha;Sklar,LarryA.;Kotz,JoanneD.;Clish,ClaryB.;Sadreyev,RuslanI.;Clemons,PaulA.;Janzer,Andreas;Schreiber,StuartL.;Scadden,DavidT.[Cell,2016,vol.167,#1,p.171-15,186]

[3]CurrentPatentAssignee:CLEARCREEKBIOINC-US2021/292280,2021,A1Locationinpatent:Paragraph0141-0144

[1]Madak,JosephT.;Cuthbertson,ChristineR.;Chen,Wenmin;Showalter,HollisD.;Neamati,Nouri[Chemistry-AEuropeanJournal,2017,vol.23,#56,p.13875-13878]

Literature

Title: On dihydroorotate dehydrogenases and their inhibitors and uses.

Journal: Journal of medicinal chemistry 20130425

Title: New inhibitors of dihydroorotate dehydrogenase (DHODH) based on the 4-hydroxy-1,2,5-oxadiazol-3-yl (hydroxyfurazanyl) scaffold.

Journal: European journal of medicinal chemistry 20120301

Title: Potent antiviral activity of brequinar against the emerging Cantagalo virus in cell culture.

Journal: International journal of antimicrobial agents 20111101

Title: Discovery of novel inhibitors for DHODH via virtual screening and X-ray crystallographic structures.

Journal: Bioorganic & medicinal chemistry letters 20100315

Title: The structures of human dihydroorotate dehydrogenase with and without inhibitor reveal conformational flexibility in the inhibitor and substrate binding sites.

Journal: Biochemistry 20080826

Title: Biochemical characterization of recombinant dihydroorotate dehydrogenase from the opportunistic pathogenic yeast Candida albicans.

Journal: The FEBS journal 20060701

Title: Brequinar derivatives and species-specific drug design for dihydroorotate dehydrogenase.

Journal: Bioorganic & medicinal chemistry letters 20060315

Title: Dual binding mode of a novel series of DHODH inhibitors.

Journal: Journal of medicinal chemistry 20060223

Title: Biphenyl-4-ylcarbamoyl thiophene carboxylic acids as potent DHODH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20060115

Title: Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase.

Journal: Bioorganic & medicinal chemistry 20050315

Title: Inhibitor binding in a class 2 dihydroorotate dehydrogenase causes variations in the membrane-associated N-terminal domain.

Journal: Protein science : a publication of the Protein Society 20040401

Title: Malarial dihydroorotate dehydrogenase. Substrate and inhibitor specificity.

Journal: The Journal of biological chemistry 20021101

Title: In vitro and in Vivo inhibition of immunoglobulin secretion by the immunosuppressive compound HR325 is reversed by exogenous uridine.

Journal: Scandinavian journal of immunology 20020701

Title: Inhibition of cyclosporin-resistant B-cell antigen responses by pyrazoles: a tool for the identification of novel molecular mechanisms of B-cell activation.

Journal: Transplantation proceedings 20010501

Title: Multiple inhibitor analysis of the brequinar and leflunomide binding sites on human dihydroorotate dehydrogenase.

Journal: Biochemistry 20010220

Title: Anti-arthritic effects of KF20444, a new immunosuppressive compound inhibiting dihydroorotate dehydrogenase, on rat collagen-induced arthritis.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20010101

Title: Immunosuppressive drugs: the first 50 years and a glance forward.

Journal: Immunopharmacology 20000501

Title: Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid.

Journal: Chemico-biological interactions 20000103

Title: Species-related inhibition of human and rat dihydroorotate dehydrogenase by immunosuppressive isoxazol and cinchoninic acid derivatives.

Journal: Biochemical pharmacology 19981101

Title: Structural and functional comparison of agents interfering with dihydroorotate, succinate and NADH oxidation of rat liver mitochondria.

Journal: Biochemical pharmacology 19981015

Title: 2',3'-Didehydro-3'-deoxythymidine: regulation of its metabolic activation by modulators of thymidine-5'-triphosphate biosynthesis.

Journal: Molecular pharmacology 19960701

Title: Phase I clinical and pharmacokinetic trial of Brequinar sodium (DuP 785; NSC 368390).

Journal: Cancer research 19890815

Title: The role of the tail in temperature regulation of the cotton rat, Sigmodon hispidus.

Journal: Comparative biochemistry and physiology. A, Comparative physiology 19751201

Title: Schnellrath LC, et al. Potent antiviral activity of brequinar against the emerging Cantagalo virus in cell culture. Int J Antimicrob Agents. 2011 Nov;38(5):435-41.

Title: Qing M, et al. Characterization of dengue virus resistance to brequinar in cell culture. Antimicrob Agents Chemother. 2010 Sep;54(9):3686-95.

Title: Xu X, et al. In vitro and in vivo mechanisms of action of the antiproliferative and immunosuppressive agent, brequinar sodium. J Immunol. 1998 Jan 15;160(2):846-53.

Title: Zeping Zuo, et al. Bifunctional Naphtho,3-d,2,3triazole-4,9-dione Compounds Exhibit Antitumor Effects In Vitro and In Vivo by Inhibiting Dihydroorotate Dehydrogenase and Inducing Reactive Oxygen Species Production. J Med Chem. 2020 Jun 4.

Title: David C Schultz, et al. Pyrimidine inhibitors synergize with nucleoside analogues to block SARS-CoV-2. Nature. 2022 Feb 7.

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Tags:96187-53-0 Molecular Formula|96187-53-0 MDL|96187-53-0 SMILES|96187-53-0 6-Fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid |Heterocyclic_Building_Blocks