Basic information
- CAS
129-56-6- Standard SMILES
O=C1c2ccccc2-c2n[nH]c3cccc1c23- InChIKey
ACPOUJIDANTYHO-UHFFFAOYSA-N- Molecular formula
- C14H8N2O
- Average molar mass
- 220.23 g/mol
- Monoisotopic mass
- 220.06366288
Overview
Anthra[1,9-cd]pyrazol-6(2H)-one is a member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase. It has a role as a geroprotector, an antineoplastic agent and a c-Jun N-terminal kinase inhibitor. It is a cyclic ketone, an aromatic ketone and an anthrapyrazole.
Names & identifiers
- Preferred name
- anthra(1,9-cd)pyrazol-6(2H)-one
- IUPAC
- 14,15-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2,4,6,9(16),10,12-heptaen-8-one
- English name
- 1,9-Pyrazoloanthrone
- Molecular formula
- C14H8N2O
- Molecular weight
- 220.23
Names & synonyms
129-56-61,9-PyrazoloanthroneSP600125PyrazolanthronePyrazoleanthroneAnthra[1,9-cd]pyrazol-6(2H)-oneANTHRA(1,9-cd)PYRAZOL-6(2H)-ONE2H-Dibenzo[cd,g]indazol-6-oneC.I. 703002h-dibenzo(cd,g)indazol-6-oneDTXSID2040525NSC75890
Show more names
1PMVJNKIICS-548Anthra Hc.i.70300PyrazoxanoneSP600125 >99%
1TW30Y2766DTXCID0020525CHEBI:90695RefChem:11303814,15-diazatetracyclo(7.6.1.0^(2,7).0^(13,16))hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-8-one204-955-6Dibenzo[cd,g]indazol-6(2H)-oneSP 600125
Database identifiers
- CAS
129-56-6- PubChem CID
- 8515
- DTXSID
DTXSID2040525- ChEMBL
CHEMBL1725279、CHEMBL7064- ChEBI
CHEBI:90695- UNII
- 1TW30Y2766
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 45.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 343
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 281 · 281~282℃
- Boiling point
- 361.16 °C · 361.16°C (rough estimate)
- Density
- 1.1702 · 1.1702 (rough estimate)
- refractive index
- 1.591 · 1.5910 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: insoluble
- form
- Yellowish orange solid
- pka
- 11.75 · 11.75±0.20(Predicted)
- color
- yellow
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months
- InChI
- InChI=1S/C14H8N2O/c17-14-9-5-2-1-4-8(9)13-12-10(14)6-3-7-11(12)15-16-13/h1-7H,(H,15,16)
- InChIKey
- ACPOUJIDANTYHO-UHFFFAOYSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CB4585000
- hs_code
- 29339900
- Toxicity
- LD50 ivn-mus: 178 mg/kg CSLNX* NX#00640
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationAnthra[1,9-cd]pyrazol-6(2H)-one: ACTIVE
Applications
DescriptionSP-600125 (129-56-6) is a selective inhibitor of c-Jun N-terminal kinase (JNK). Reversibly inhibits JNK1,2 and 3 (IC50‘s range from 40-90 nM). >300-fold selectivity for JNK as compared to related MAP kinases. Anti-inflammatory activity. SP-600125 inhibits expression of presenilin-1 and Notch signaling in mouse brain. Cell permeable and active in vivo.
UsesC2C12 myoblasts were treated with SP600125 to test the stimulation of myogenesis.11 It was used to treat HepG2 cells to test the effects on oxysterol-induced necrosis.12
UsesA broad-spectrum serine/threonine kinase inhibitor of JNK with an IC50 range from 40 to 90 nM.
UsesSP 600125 is a Jun N-terminal kinase (JNK) inhibitor.
General DescriptionA potent, cell-permeable, selective, and reversible inhibitor of c-Jun N-terminal kinase (JNK) (IC50 = 40 nM for JNK-1 and JNK-2 and 90 nM for JNK-3). The inhibition is competitive with respect to ATP. Exhibits over 300-fold greater selectivity for JNK as compared to ERK1 and p38-2 MAP kinases. Inhibits the phosphorylation of c-Jun and blocks the expression of IL-2, IFN-γ, TNF-α, and COX-2 in cells. Blocks IL-1-induced accumulation of phospho-Jun and induction of c-Jun transcription.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
4 records
Compound notes
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