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170632-47-0

170632-47-0 Structure

170632-47-0 Structure
IdentificationBack Directory
[Name]

YC-1
[CAS]

170632-47-0
[Synonyms]

YC-1
CS-2261
Nsc728165
LIFICIGUAT
YC-1(Lificiguat)
Lificiguat(YC-1)
YC 1 (pharMaceutical)
YC-1 - CAS 170632-47-0 - Calbiochem
1-benzyl-3-(5-hydroxymethyl-2-furyl)indazole
1-Benzyl-3-(5-hydroxymethylfur-2-yl)indazole
3-(5'-HYDROXYMETHYL-2'-FURYL)-1-BENZYLINDAZOLE
1-benzyl-3-(5-hydroxymethyl-furan-2-yl)indazole
(5-(1-Benzyl-1H-indazol-3-yl)furan-2-yl)Methanol
5-[1-(PHENYLMETHYL)-1H-INDAZOL-3-YL]-2-FURANMETHANOL
2-Furanmethanol, 5-[1-(phenylmethyl)-1H-indazol-3-yl]-
YC-1 (3-(5'-HYDROXYMETHYL-2'-FURYL)-1-BE NZYL INDAZOLE) \ GUANYLYL CYCLASE ACTI
[Molecular Formula]

C19H16N2O2
[MDL Number]

MFCD06407798
[MOL File]

170632-47-0.mol
[Molecular Weight]

304.34
Chemical PropertiesBack Directory
[Melting point ]

110-112℃
[Boiling point ]

522.2±50.0 °C(Predicted)
[density ]

1.24±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMSO: 12 mg/mL
[form ]

solid
[pka]

13.83±0.10(Predicted)
[color ]

white
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
[InChI]

1S/C19H16N2O2/c22-13-15-10-11-18(23-15)19-16-8-4-5-9-17(16)21(20-19)12-14-6-2-1-3-7-14/h1-11,22H,12-13H2
[InChIKey]

OQQVFCKUDYMWGV-UHFFFAOYSA-N
Safety DataBack Directory
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

YC-1 (170632-47-0) is a nitric oxide-independent activator of soluble guanylyl cyclase (sGC). Significantly elevates cGMP levels and inhibits collagen-stimulated aggregation of rabbit platelets (IC50?= 14.6 μM).1?Induces human endometrial cancer cell senescence via modulation of HIF1α activity.2?Induces degradation of HIF1α.3?Protects against glutamate-induced neuronal damage4?and β-amyloid-induced toxicity in differentiated PC12 cells5.
[Uses]

YC-1 has been used as a hypoxia-inducible factor 1α (HIF-1α) inhibitor:
  • to reduce hypoxia induced Jagged1 expression in cardiomyocytes (CMs)
  • to study its effect on progenitor expansion and CD34+ and side population (SP) cell phenotype and on the proliferation rate of cells with an ability to form long term colony forming units
  • to study its effect on regulating sphingosine 1-phosphate (S1P) bound to albumin induced plasminogen activator inhibitor 1 (PAI-1) expression by activating Rho/ Rho-associated protein kinase (ROCK) pathway.

[Definition]

ChEBI: Lificiguat is a member of the class of indazoles that is 1H-indazole which is substituted by a benzyl group at position 1 and a 5-(hydroxymethyl)-2-furyl group at position 3. It is an activator of soluble guanylate cyclase and inhibits platelet aggregation. It has a role as an antineoplastic agent, a soluble guanylate cyclase activator, an apoptosis inducer, a platelet aggregation inhibitor and a vasodilator agent. It is a member of indazoles, a member of furans and an aromatic primary alcohol.
[General Description]

A nitric oxide-independent, superoxide-sensitive activator of soluble guanylyl cyclase. Inhibits platelet adhesion to collagen and acts as an antithrombotic agent. Reported to reduce HIF-1α levels and xenograft growth.
[Biochem/physiol Actions]

YC-1 activates soluble guanylyl cyclase and prevents platelet aggregation and vascular contraction. It has a potential to treat circulation disorders. YC-1 also has an ability to inhibit hypoxia-inducible factor 1α (HIF-1α) activity in vitro. It acts as a potential antiangiogenic anticancer agent.
[storage]

+4°C
[References]

1) Martin?et al.?(2001),?YC-1 activation of human soluble guanylyl cyclase has both heme-dependent and heme-independent components;?Proc. Natl. Acad. Sci. USA,?98?12938 2) Kato?et al.?(2006),?Induction of human endometrial cancer cell senescence through modulation of HIF-1alpha activity by EGLN1; Int. J. Cancer,?118?1144 3) Kim?et al.?(2006),?A domain responsible for HIF-1alpha degradation by YC-1, a novel anticancer agent; Int. J. Oncol.,?29?255 4) Tai?et al. (2018),?Therapeutic window for YC-1 following glutamate-induced neuronal damage and transient focal cerebral ischemia; Mol. Med. Rep.,?17?6490 5) Tsai?et al.?(2013),?The role of heat shock protein 70 in the protective effect of YC-1 on β-amyloid-induced toxicity in differentiated PC12 cells.; PLoS One,?8(7)?e69320
Spectrum DetailBack Directory
[Spectrum Detail]

YC-1(170632-47-0)1HNMR
170632-47-0 suppliers list
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