170632-47-0

Basic information

• Product Name: YC-1
• Synonyms: 2-Furanmethanol, 5-[1-(phenylmethyl)-1H-indazol-3-yl]-;Nsc728165;(5-(1-Benzyl-1H-indazol-3-yl)furan-2-yl)Methanol;YC 1 (pharMaceutical);1-Benzyl-3-(5-hydroxymethylfur-2-yl)indazole;1-benzyl-3-(5-hydroxymethyl-furan-2-yl)indazole;Lificiguat(YC-1);5-[1-(PHENYLMETHYL)-1H-INDAZOL-3-YL]-2-FURANMETHANOL
• CAS NO: 170632-47-0
• Molecular Formula: C₁₉H₁₆N₂O₂
• Molecular Weight: 304.34
• Mol File: 170632-47-0.mol

Chemical Properties

• Melting Point: 110-112℃
• Boiling Point: 522.2±50.0 °C(Predicted)
• Appearance: white/solid
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: -20C
• Solubility: DMSO: 12 mg/mL
• PKA: 13.83±0.10(Predicted)
• 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.
• CAS DataBase Reference: YC-1(CAS DataBase Reference)
• NIST Chemistry Reference: YC-1(170632-47-0)
• EPA Substance Registry System: YC-1(170632-47-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 170632-47-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
YC-1 is used as a hypoxia-inducible factor 1α (HIF-1α) inhibitor for reducing hypoxia-induced Jagged1 expression in cardiomyocytes (CMs). It is also used to study its effect on progenitor expansion and CD34+ and side population (SP) cell phenotype, as well as on the proliferation rate of cells with an ability to form long-term colony-forming units.
Used in Cardiovascular Research:
YC-1 is used as an antithrombotic agent, inhibiting platelet adhesion to collagen and reducing the risk of blood clot formation.
Used in Cancer Research:
YC-1 is used to study its effect on regulating sphingosine 1-phosphate (S1P) bound to albumin-induced plasminogen activator inhibitor 1 (PAI-1) expression by activating the Rho/Rho-associated protein kinase (ROCK) pathway. Additionally, it induces human endometrial cancer cell senescence via modulation of HIF1α activity and induces degradation of HIF1α.
Used in Neuroprotection:
YC-1 is used to protect against glutamate-induced neuronal damage and β-amyloid-induced toxicity in differentiated PC12 cells, demonstrating its potential in neuroprotection.

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.

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

Upstream product

• 611-13-2 2-furoic acid methyl ester 
• 205643-28-3 N-benzyl-3-iodo-1H-indazole 
• 98-03-3 thiophene-2-carbaldehyde 
• 13436-48-1 1-methyl-1H-indazole 
• 6630-33-7 ortho-bromobenzaldehyde 
• 3878-19-1 3-(furan-2-yl)-1H-indazole 
• 215789-59-6 Trifluoro-methanesulfonic acid 1-benzyl-1H-indazol-3-yl ester 
• 100-44-7 benzyl chloride 
• 7364-25-2 3-indazolinone 
• 2215-63-6 1-benzyl-1,2-dihydro-3H-indazol-3-one 
• 2527-99-3 methyl 5-bromo-2-furoate 
• 66607-27-0 3-iodoindazole 
• 271-44-3 benzimidazole 
• 353504-65-1 5-(2-nitro-benzoyl)-furan-2-carboxylic acid methyl ester 

Downstream Products

• 205643-09-0 1-Benzyl-3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-1H-indazole 
• 1151561-51-1 C₃₆H₂₉N₃O₅ 
• 1151561-52-2 C₃₇H₃₁N₃O₅ 
• 1345965-42-5 C₂₄H₂₄N₂O₃ 
• 1345965-41-4 C₂₃H₂₂N₂O₃ 
• 205643-03-4 1-benzyl-3-(5-formyl-furan-2-yl)indazole 
• 849330-91-2 [5-(1-benzyl-1H-indazol-3-yl)-tetrahydro-furan-2-yl]methanol 
• 205643-06-7 3-(5-Azidomethylfuran-2-yl)-1-benzyl-indazole 
• 865757-06-8 succinic acid mono-[5-(1-benzyl-1H-indazol-3-yl)-furan-2-ylmethyl]ester 

Relevant articles and documents

Hypoxia-Targeting Organometallic Ru(II)-Arene Complexes with Enhanced Anticancer Activity in Hypoxic Cancer Cells

As hypoxia is an important factor to limit chemotherapeutic efficacy in tumors, we herein report three ruthenium(II)-arene complexes containing a hypoxia inducible factor-1α inhibitor (YC-1), which endow the organometallic complexes with potential for hyp

Suzuki-type cross-coupling reaction of 3-iodoindazoles with aryl boronic acids: A general and flexible route to 3-arylindazoles

This paper describes a Suzuki Type cross coupling reaction of 3- iodoindazoles with aryl and heteroaryl boronic acids as a general route to 3- arylindazoles. The coupling reaction is illustrated by the preparation of new aryl- or heteroarylindazoles 7. Scope and limitation of the method are outlined. The coupling reaction works best on a 1-substituted indazole nucleus. The usefulness of the reaction is illustrated by a short practical synthesis of YC-1, a pharmacological agent potentially useful for the treatment of cardiovascular diseases or erectile dysfunction.

Palladium-Catalyzed C-H/C-H Cross-Coupling by Mechanochemistry: Direct Alkenylation and Heteroarylation of N1-Protected 1 H-Indazoles

C3-alkenylated and C3-(hetero)arylated 1H-indazoles are privileged structural motifs in numerous pharmaceuticals. Direct C3-alkenylation and C3-(hetero)arylation of 1H-indazoles have been significantly challenging because of the inert nature of this carbon center. Herein, we present an efficient mechanochemical strategy for palladium-catalyzed C-H/C-H cross-coupling to construct C3-alkenylated and C3-heteroarylated 1H-indazoles using low-cost copper oxidants with satisfactory product yields and broad functional group tolerance. The robustness of the developed protocols was further demonstrated by the unprecedented total mechanosynthesis of the intermediate of PLK4 inhibitor CFI-400945 and HIF-1α inhibitor YC-1.

Preparation method of indazole and application of indazole in medicine synthesis

The invention belongs to the field of chemicals, and relates to a preparation method of indazole and an application of the indazole in medicine synthesis. The invention discloses a preparation method of indazole and an application of the indazole in synthesizing 1H-indazole-3-carboxylic acid, lonidamine, a compound 8, a compound 9, a compound 10, axitinib, YD-3, YC-1 and similar substances thereof.

Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles

An efficient synthesis of indazoles from readily accessible E/Z mixtures of o-haloaryl N-tosylhydrazones has been developed. The thermo-induced isomerization of N-tosylhydrazones is discussed. A series of valuable indazole derivatives are prepared in good yields, and the method has been successfully applied to the synthesis of the bioactive compounds, lonidamine, AF-2785, axitinib, YC-1 and YD-3.

The design, synthesis, and biological evaluation of novel YC-1 derivatives as potent anti-hepatic fibrosis agents

1-Benzyl-3-(substituted aryl)-5-methylfuro[3,2-c]pyrazole (YC-1) is a well-known synthetic compound with various satisfactory pharmacological activities, such as the activation of soluble guanylate cyclase (sGC) and the inhibition of hypoxia-induced facto

Pd- and Cu-catalyzed C-H arylation of indazoles

The palladium- and copper-catalyzed C-H arylation reactions of 1H- and 2H-indazoles with haloarenes are described. A PdCl2/phen/Ag 2CO3/K3PO4 catalytic system is effective for the C-H arylation of 1H- and 2H-indazoles with haloarenes, whereas a less expensive CuI/phen/LiOt-Bu catalytic system is applicable to the C-H coupling of substituted 2H-indazoles and iodoarenes. The utility of newly developed catalyst was demonstrated in the rapid synthesis of YC-1 (an antitumor agent) and YD-3 (platelet anti-aggregating agent). These new reactions represent important direct functionalization tools of indazoles, well-known bioisosteres of pharmaceutically important indole core.

Design, synthesis and insight into the structure-activity relationship of 1,3-disubstituted indazoles as novel HIF-1 inhibitors

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Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: Successive Amberlyst A21- and Amberlyst 15-catalyzed processes

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Cancer chemotherapy

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