CB5083
- CAS No.
- 1542705-92-9
- Chemical Name:
- CB5083
- Synonyms
- CB5083;CS-1553;CB-5083;EOS-61078;CB 5083;CB5083;CB-5083, 10 mM in DMSO;CB5083; CB-5083; CB 5083.;1-[4-(benzylamino)-5H,7H,8H-pyrano[4,3-d]pyrimidin-2-yl]-2-methyl-1H-indole-4-carboxamide;1-[4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl]-2-methylindole-4-carboxamide;1-(4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)-2-methyl-1H-indole-4-carboxamide
- CBNumber:
- CB72749007
- Molecular Formula:
- C24H23N5O2
- Molecular Weight:
- 413.47
- MDL Number:
- MFCD28963914
- MOL File:
- 1542705-92-9.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Boiling point | 760.5±70.0 °C(Predicted) |
|---|---|
| Density | 1.37±0.1 g/cm3(Predicted) |
| storage temp. | Store at -20°C |
| solubility | insoluble in H2O; ≥20.65 mg/mL in DMSO; ≥4.4 mg/mL in EtOH |
| form | solid |
| pka | 15.99±0.30(Predicted) |
| color | White to light yellow |
| InChIKey | RDALZZCKQFLGJP-UHFFFAOYSA-N |
| SMILES | N1(C2=NC(NCC3=CC=CC=C3)=C3COCCC3=N2)C2=C(C(C(N)=O)=CC=C2)C=C1C |
| FDA UNII | 591IV6UL6J |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319-H335 |
| Precautionary statements | P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501 |
CB5083 price More Price(58)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 19311 | CB-5083 ≥95% | 1542705-92-9 | 1mg | $49 | 2026-04-30 | Buy |
| Cayman Chemical | 19311 | CB-5083 ≥95% | 1542705-92-9 | 5mg | $146 | 2026-04-30 | Buy |
| Cayman Chemical | 19311 | CB-5083 ≥95% | 1542705-92-9 | 10mg | $267 | 2026-04-30 | Buy |
| Cayman Chemical | 19311 | CB-5083 ≥95% | 1542705-92-9 | 25mg | $603 | 2026-04-30 | Buy |
| ChemScene | CS-5405 | CB-5083 99.90% | 1542705-92-9 | 5mg | $119 | 2026-06-04 | Buy |
CB5083 Chemical Properties, Uses, Production
Uses
CB-5083 is a first-in-class, potent, selective, and orally bioavailable inhibitor of the p97 AAA ATPase/VCP. CB-5083 selectively inhibits p97 through its D2 site with the IC50 of 11 nM[1].
Biological Activity
cb-5083 is an orally bioavailable inhibitor of p97. p97 is an aaa-atpase involved in multiple cellular functions such as organelle membrane homotypic fusion and sorting of endosomal cargo. p97 is also known as valosin-containing protein which plays important roles in regulating protein homeostasis [1].
Synthesis
![1-(4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)-2-methyl-1H-indole-4-carbonitrile](/CAS/20180703/GIF/1542705-83-8.gif)
1542705-83-8
1542705-92-9
Compound 7 (CAS:1542705-83-8, 180 mg, 0.46 mmol) was used as a raw material and dissolved in a mixed solvent of ethanol (8 mL) and water (1 mL). Palladium acetate (Pd(OAc)2, 11 mg, 0.046 mmol), triphenylphosphine (PPh3, 14 mg, 0.053 mmol), and acetaldehyde oxime (53 mg, 0.92 mmol) were then added sequentially. The reaction mixture was heated to reflux for 2 hours. After completion of the reaction, the mixture was concentrated and the residue was purified by fast column chromatography (silica gel as stationary phase and dichloromethane/methanol=20:1 as eluent) to afford the target product 1-(4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)-2-methyl-1H-indole-4-carboxamide (II, 110 mg, Yield 58%). Mass spectrometry (LRMS) analysis of the product showed that the calculated value of (M+H)+ m/z was 414.19 and the measured value was 414.20. Nuclear magnetic resonance hydrogen spectrometry (1H-NMR, 300 MHz, D3COD) data were as follows: δ 7.72 (d, 1H), 7.44 (d, 1H), 7.41 (m, 1H), 7.31 (m, 3H), 7.25 (m, 1H), 6.96 (t, 1H), 6.77 (s, 1H), 4.71 (d, 2H), 4.63 (s, 1H), 4.05 (t, 2H), 2.11 (t, 2H), 2.45 (s, 3H).
in vitro
cb-5083 is a selective potent inhibitor of p97’s second atpase domain. cb-5083 might compete with atp for the same binding site but may adopt a different orientation[2]. the ic50 of cb-5083 against wild-type (wt) p97 was 15.4 nm. cb-5083 could dose-dependently increase the cytosolic protein degradation in hek293t, a549 and hct116 cell lines [1]. cb-5083 treatment (2.5 μm) of a549 cells for 24h could induce cancer cell death [1].
in vivo
in female nude mice bearing hct116, a549 lung carcinoma, and amo-1 multiple myeloma xenograft tumors, oral administration of cb-5083 (100 mg/kg) for 6 h showed a significant antitumor response in tumors (tgi = 63%, p < 0.0001) [1,2].
IC 50
15.4 nm
storage
Store at -20°C
References
anderson d j, le moigne r, djakovic s, et al. targeting the aaa atpase p97 as an approach to treat cancer through disruption of protein homeostasis[j]. cancer cell, 2015, 28(5): 653-665.zhou h j, wang j, yao b, et al. discovery of a first-in-class, potent, selective, and orally bioavailable inhibitor of the p97 aaa atpase (cb-5083)[j]. journal of medicinal chemistry, 2015, 58(24): 9480-9497.
CB5083 Preparation Products And Raw materials
Raw materials
1of2
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Jinan Jiuli Biotechnology Co. , Ltd. | 15865264761 | 486064515@qq.com | China | 5000 | 58 |
| Shanghai Boyle Chemical Co., Ltd. | sales@boylechem.com | China | 2915 | 55 | |
| WUHAN SUN-SHINE BIO-TECHNOLOGY Co., Ltd. | 17702719238 | sales@sun-shinechem.com | China | 1197 | 64 |
| Dalian Meilun Biotech Co., Ltd. | 0411-62910999 13889544652 | sales@meilune.com | China | 4765 | 58 |
| Shanghai Jian Chao Chemical Technology Co., Ltd. | 150-2103-5486 18017383231 | 983544897@qq.com | China | 9335 | 55 |
| Haoyuan Chemexpress Co., Ltd. | 021-58950125 | info@chemexpress.com | China | 7545 | 61 |
| SINO High Goal Chemical Technology Co., Ltd. | 021-57646680 18306277365 | sunkai@chembiobanksh.com | China | 2039 | 55 |
| AdooQ Bioscience CHINA | 025-58849295 | info@adooq.cn | China | 2981 | 60 |
| Shanghai Lollane Biological Technology Co.,Ltd. | 021-52996696，15000506266 15000506266 | China | 4859 | 55 | |
| Shanghaizehan biopharma technology co., Ltd. | 021-61350663 13052117465 | sales@zehanbiopharma.com | China | 989 | 55 |
