BMS 740808

For research use only. Not for therapeutic Use.

  • CAT Number: I004643
  • CAS Number: 280118-23-2
  • Molecular Formula: C31H27F3N6O3
  • Molecular Weight: 588.591
  • Purity: ≥95%
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BMS-740808 is a highly potent, selective inhibitor of Factor X, with Ki of 0.03 nM. BMS-740808 is highly potent with a rapid onset of inhibition (2.7 × 107 M-1 s-1). BMS-740808 is synthesized by modification of employing bicyclic pyrazolo-pyridinone scaffold to Razaxaban, a pyrazole based Factor X inhibitor.


Catalog Number I004643
CAS Number 280118-23-2
Synonyms

BMS 740808; BMS-740808; BMS740808; UNII-LDD74E663F;;7H-Pyrazolo(3,4-c)pyridin-7-one, 1-(3-amino-1,2-benzisoxazol-5-yl)-1,4,5,6-tetrahydro-6-(2/’-(((3R)-3-hydroxy-1-pyrrolidinyl)methyl)(1,1/’-biphenyl)-4-yl)-3-(trifluoromethyl)-

Molecular Formula C31H27F3N6O3
Purity ≥95%
Target Inhibitor of Factor X
Solubility Soluble in DMSO, not in water
Storage 0 - 4 °C for short term or -20 °C for long term
IUPAC Name 1-(3-amino-1,2-benzoxazol-5-yl)-6-[4-[2-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]phenyl]phenyl]-3-(trifluoromethyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one
InChI InChI=1S/C31H27F3N6O3/c32-31(33,34)28-24-12-14-39(30(42)27(24)40(36-28)21-9-10-26-25(15-21)29(35)37-43-26)20-7-5-18(6-8-20)23-4-2-1-3-19(23)16-38-13-11-22(41)17-38/h1-10,15,22,41H,11-14,16-17H2,(H2,35,37)/t22-/m1/s1
InChIKey DFRIQJHMGZBFOM-JOCHJYFZSA-N
SMILES C1CN(CC1O)CC2=CC=CC=C2C3=CC=C(C=C3)N4CCC5=C(C4=O)N(N=C5C(F)(F)F)C6=CC7=C(C=C6)ON=C7N
Reference

1:Bioorg Med Chem Lett. 2006 Aug 1;16(15):4141-7. Epub 2006 May 30. 1-[3-Aminobenzisoxazol-5/’-yl]-3-trifluoromethyl-6-[2/’-(3-(R)-hydroxy-N-pyrrolidinyl)methyl-[1,1/’]-biphen-4-yl]-1,4,5,6-tetrahydropyrazolo-[3,4-c]-pyridin-7-one (BMS-740808) a highly potent, selective, efficacious, and orally bioavailable inhibitor of blood coagulation factor Xa.Pinto DJ,Orwat MJ,Quan ML,Han Q,Galemmo RA Jr,Amparo E,Wells B,Ellis C,He MY,Alexander RS,Rossi KA,Smallwood A,Wong PC,Luettgen JM,Rendina AR,Knabb RM,Mersinger L,Kettner C,Bai S,He K,Wexler RR,Lam PY, PMID: 16730984 DOI: 10.1016/j.bmcl.2006.02.069 </br><span>Abstract:</span> Attempts to further optimize the pyrazole factor Xa inhibitors centered on masking the aryl aniline P4 moiety. Scaffold optimization resulted in the identification of a novel bicyclic pyrazolo-pyridinone scaffold which retained fXa potency. The novel bicyclic scaffold preserved all binding interactions observed with the monocyclic counterpart and importantly the carboxamido moiety was integrated within the scaffold making it less susceptible to hydrolysis. These efforts led to the identification of 1-[3-aminobenzisoxazol-5/’-yl]-3-trifluoromethyl-6-[2/’-(3-(R)-hydroxy-N-pyrrolidinyl)methyl-[1,1/’]-biphen-4-yl]-1,4,5,6-tetrahydropyrazolo-[3,4-c]-pyridin-7-one 6f (BMS-740808), a highly potent (fXa Ki=30 pM) with a rapid onset of inhibition (2.7×10(7) M-1 s-1) in vitro, selective (>1000-fold over other proteases), efficacious in the AVShunt thrombosis model, and orally bioavailable inhibitor of blood coagulation factor Xa.

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