3-(5'-Hydroxymethyl-2'-furyl)-1-benzylindazole
Basic information
- CAS
170632-47-0- Standard SMILES
OCc1ccc(-c2nn(Cc3ccccc3)c3ccccc23)o1- InChIKey
OQQVFCKUDYMWGV-UHFFFAOYSA-N- Molecular formula
- C19H16N2O2
- Average molar mass
- 304.3 g/mol
- Monoisotopic mass
- 304.12117776
Overview
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 vasodilator agent, a platelet aggregation inhibitor, an apoptosis inducer and a soluble guanylate cyclase activator. It is a member of furans, an aromatic primary alcohol and a member of indazoles.
Names & identifiers
- Preferred name
- 3-(5'-Hydroxymethyl-2'-furyl)-1-benzylindazole
- IUPAC
- [5-(1-benzylindazol-3-yl)furan-2-yl]methanol
- English name
- YC-1
- Molecular formula
- C19H16N2O2
- Molecular weight
- 304.34
Names & synonyms
3-(5'-Hydroxymethyl-2'-furyl)-1-benzylindazole154453-18-6YC 1 compoundRefChem:911021yc-1Lificiguat170632-47-0(5-(1-benzyl-1H-indazol-3-yl)furan-2-yl)methanolYC 1[5-(1-benzylindazol-3-yl)furan-2-yl]methanolLificiguat [INN]MFCD06407798
Show more names
CS-2261Nsc728165Lificiguat(YC-1)YC-1(Lificiguat)YC 1 (pharMaceutical)Lificiguat, 10 mM in DMSOYC-1, guanylyl cyclase activatorYC-1 - CAS 170632-47-0 - Calbiochem
515CC1WPTE[5-(1-benzyl-1H-indazol-3-yl)furan-2-yl]methanolCHEMBL3339853-(5'-Hydroxymethyl-2'-furyl)-1-benzyl indazole3-(5/'-hydroxymethyl-2/'-furyl)-1-benzylindazoleNSC-728165YC11-Benzyl-3-(5-hydroxymethyl-2-furyl)indazole
Database identifiers
- CAS
170632-47-0- PubChem CID
- 5712
- DTXSID
DTXSID70165635
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 51.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 386
Physicochemical properties
- Melting point
- 110 · 110-112℃
- Boiling point
- 522.2 · 522.2±50.0 °C(Predicted)
- Density
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 12 mg/mL · DMSO: 12 mg/mL
- pka
- 13.83 · 13.83±0.10(Predicted)
- form
- solid
- color
- white
- Stability
- 2 years · 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
- FDA UNII
- 515 CC1WPTE · 515CC1WPTE
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Compounds or factors that act on a specific enzyme to increase its activity.
Applications
DescriptionYC-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).1Induces human endometrial cancer cell senescence via modulation of HIF1α activity.2Induces degradation of HIF1α.3Protects against glutamate-induced neuronal damage4and β-amyloid-induced toxicity in differentiated PC12 cells5.
UsesYC-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 unitsto 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.
General DescriptionA 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.
Additional notes
DefinitionChEBI: 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.
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