Iwp-2
Basic information
- CAS
686770-61-6- Standard SMILES
Cc1ccc2nc(NC(=O)CSc3nc4c(c(=O)n3-c3ccccc3)SCC4)sc2c1- InChIKey
WRKPZSMRWPJJDH-UHFFFAOYSA-N- Molecular formula
- C22H18N4O2S3
- Average molar mass
- 466.6 g/mol
- Monoisotopic mass
- 466.05918935
Overview
IWP-2 is a thienopyridine that is 6,7-dihydrothieno[3,2-d]pyrimidin-4(3H)-one substituted by {2-[(6-methyl-1,3-benzothiazol-2-yl)amino]-2-oxoethyl}sulfanediyl and phenyl groups at positions 2 and 3, respectively. It is an ATP-competitive CK1delta inhibitor and also a Wnt/beta-catenin signal pathway inhibitor. It has a role as an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor and a Wnt signalling inhibitor. It is a secondary carboxamide, an organic sulfide, a member of benzenes, a thienopyridine and a member of benzothiazoles.
Names & identifiers
- Preferred name
- Iwp-2
- IUPAC
- N-(6-methyl-1,3-benzothiazol-2-yl)-2-[(4-oxo-3-phenyl-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)sulfanyl]acetamide
- English name
- IWP-2
- Molecular formula
- C22H18N4O2S3
- Molecular weight
- 466.6
Names & synonyms
IWP-2686770-61-6DTXSID50366724RefChem:1087882DTXCID20317763IWP 2N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-acetamideN-(6-methylbenzo[d]thiazol-2-yl)-2-((4-oxo-3-phenyl-3,4,6,7-tetrahydrothieno[3,2-d]pyrimidin-2-yl)thio)acetamideMFCD04457599CID 2155128IWP-2 (GMP)CHEMBL1257064
Show more names
CS-803IWP IWPIWP-2-salt2IWP 2, >=98%IWP-2 USP/EP/BPWNT INHIBITOR IWP-2IWP-2, 10 mM in DMSOABC 294640ABC-294640
HMS3652J22EX-A2264BDBM50428028N-(6-methyl-1,3-benzothiazol-2-yl)-2-[(4-oxo-3-phenyl-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)sulfanyl]acetamideIWP-2, >=98% (HPLC)CS-0626098N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]acetamideN-(6-Methylbenzo[d]thiazol-2-yl)-2-(4-oxo-3-phenyl-3,4,6,7-tetrahydrothieno[3,2-d]pyrimidin-2-ylthio)acetamide
Properties
Computed structural properties
- XLogP
- 4.8
- Topological polar surface area
- 154 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 796
Physicochemical properties
- Melting point
- 257 °C · 257 °C(dec.)
- Density
- 1.52 · 1.52±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- 5 mg/mL · DMSO: >5mg/mL
- pka
- 9.01 · 9.01±0.70(Predicted)
- form
- powder
- color
- Beige
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
- InChI
- InChI=1S/C22H18N4O2S3/c1-13-7-8-15-17(11-13)31-21(23-15)25-18(27)12-30-22-24-16-9-10-29-19(16)20(28)26(22)14-5-3-2-4-6-14/h2-8,11H,9-10,12H2,1H3,(H,23,25,27)
- InChIKey
- WRKPZSMRWPJJDH-UHFFFAOYSA-N
- SMILES
- C(NC1=NC2=CC=C(C)C=C2S1)(=O)CSC1N(C2=CC=CC=C2)C(=O)C2SCCC=2N=1
- CAS DataBase Reference
- 686770 · 686770-61-6
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
- WGK Germany
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
- 2
- hs_code
- 2934.20.8000
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionIWP-2 is an inhibitor of Wnt processing and secretion with IC50 of 27 nM in a cell-free assay, selective blockage of Porcn-mediated Wnt palmitoylation, does not affect Wnt/β-catenin in general and displays no effect against Wnt-stimulated cellular responses.
DescriptionIWP-2 (686770-61-6) is an inhibitor of Wnt secretion and processing. It blocks Wnt-dependent signaling (IC50= 27 nM) by inhibition of the O-acyltransferase Porcn.1 Induces cardiomyocyte differentiation from human pluripotent stem cells.2 IWP-2 is an important tool to probe the involvement of the Wnt pathway in physiological processes.3,4Cell permeable.
UsesIWP-2 has been used to treat the cell lines L-Wnt-3a and L-Wnt-5a, to demonstrate the inhibitory effect of IWP-2. It has also been used as a Wnt signaling inhibitor to treat WT andGja1Jrt/+ stromal cells to confirm that, theWnt/β-catenin signaling pathway pathway was not involved in the increased marker expression byGja1Jrt/+ osteoblasts.
UsesIWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. IWP-2 is useful in the treatment diseases and conditions such as cancer, degenerative diseases, type II diabetes and osteopetrosis.
General DescriptionA cell-permeable benzothiazolyl-acetamide compound that inhibits the cellular Wnt processing and secretion via selective blockage of MBOAT (membrane-bound O-acyltranferase) family member Porcn- (Porcupine) mediated Wnt palmitoylation. IWP-2 does not affect Wnt/β-catenin signaling pathway in general and, unlike IWR-1-endo (Cat. No. 681669), displays no effect against Wnt-stimulated cellular responses. Also available as a 10 mM solution in DMSO (Cat. No. 506072).
Additional notes
DefinitionChEBI: N-(6-methyl-1,3-benzothiazol-2-yl)-2-[(4-oxo-3-phenyl-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl)thio]acetamide is an organonitrogen heterocyclic compound, an organic heterobicyclic compound and an organosulfur heterocyclic compound.
Related reactions
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Compound notes
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