ChemicalBook > CAS DataBase List > 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one

2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one

Product Name
2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one
CAS No.
1234480-50-2
Chemical Name
2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one
Synonyms
CS-641;XMD 8-92;XMD8-92 ，S7525;XMD 8-92 (free base);XMD8-92 >=98% (HPLC);XMD8-92, 10 mM in DMSO;XMD 8-92 trifluoroacetate;2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4;2-[2-ethoxy-4-(4-hydroxypiperidin-1-yl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one;2-[[2-Ethoxy-4-(4-hydroxy-1-piperidyl)phenyl]amino]-5,11-dimethyl-5H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6(11H)-one
CBNumber
CB32534669
Molecular Formula
C26H30N6O3
Formula Weight
474.55
MOL File
1234480-50-2.mol
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2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one Property

Boiling point:
741.8±70.0 °C(Predicted)
Density 
1.301
storage temp. 
Store at 4°C
solubility 
≥23.75 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH
form 
solid
pka
14.76±0.20(Predicted)
color 
Off-white to light yellow
InChIKey
QAPAJIZPZGWAND-UHFFFAOYSA-N
SMILES
OC(CC1)CCN1C2=CC=C(NC3=NC(N(C)C(C=CC=C4)=C4C(N5C)=O)=C5C=N3)C(OCC)=C2
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Safety

WGK Germany 
WGK 3
HS Code 
2933599590
Storage Class
11 - Combustible Solids
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
19173
Product name
XMD8-92
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
19173
Product name
XMD8-92
Purity
≥98%
Packaging
5mg
Price
$90
Updated
2024/03/01
Cayman Chemical
Product number
19173
Product name
XMD8-92
Purity
≥98%
Packaging
10mg
Price
$117
Updated
2024/03/01
Cayman Chemical
Product number
19173
Product name
XMD8-92
Purity
≥98%
Packaging
25mg
Price
$267
Updated
2024/03/01
Tocris
Product number
4132
Product name
XMD8-92
Purity
≥98%(HPLC)
Packaging
50
Price
$1050
Updated
2021/12/16
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2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical Properties,Usage,Production

Description

XMD8-92 is an ERK5 inhibitor (Kd = 80 nM) that less potently inhibits DCAMKL2, TNK1, and Plk4 (Kds = 190, 890, and 600 nM, respectively) in a panel of 402 kinases. It blocks ERK5 autophosphorylation, ERK5-mediated phosphorylation of promyelocytic leukemia protein (PML), and PML-dependent activation of p21. XMD8-92 inhibits AP-1 transcriptional activity induced by MEK5-activated ERK5 but not that induced by Cdc37. It inhibits bFGF-induced angiogenesis in a Matrigel™ plug assay in mice and reduces tumor growth in a HeLa mouse xenograft model when administered at a dose of 50 mg/kg twice per day. XMD8-92 also binds bromodomain-containing protein 4 (BRD4; Kd = 170 nM for BRD4 bromodomain 1).

Uses

XMD 8-92, is a BMK1 inhibitor and a highly selective inhibitor of ERK5 activity. XMD8-92 blocks cellular BMK1 activation and significantly suppresses tumor growth in lung and cervical tumor models and is well tolerated in animals.

Definition

ChEBI: XMD8-92 is a dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one carrying at C-2 on the pyrimidine ring a [2-ethoxy-4-(4-hydroxypiperidin-1-yl)phenyl]amino substituent. It is an inhibitor of the BMK1 kinase pathway. It has a role as a protein kinase inhibitor.

in vivo

XMD8-92 (i.p.; twice a day for 28 days) significantly inhibits the growth of the xenografted human tumors[1].

Animal Model:HeLa Xenograft Model (6-week-old Nod/Scid mice)[1]
Dosage:50 mg/kg
Administration:I.p.; twice a day for 28 days
Result:Significantly inhibited the growth of the xenografted human tumors.

IC 50

BMK1: 80 nM (Kd); BRD4: 190 nM (Kd)

storage

Store at RT

References

[1] QINGKAI YANG. Pharmacological inhibition of BMK1 suppresses tumor growth through promyelocytic leukemia protein.[J]. Cancer Cell, 2010: 258-267. DOI: 10.1016/j.ccr.2010.08.008
[2] TATIANA ERAZO. Canonical and kinase activity-independent mechanisms for extracellular signal-regulated kinase 5 (ERK5) nuclear translocation require dissociation of Hsp90 from the ERK5-Cdc37 complex.[J]. Molecular and Cellular Biology, 2013, 33 8: 1671-1686. DOI: 10.1128/mcb.01246-12
[3] E. C. LIN. ERK5 kinase activity is dispensable for cellular immune response and proliferation[J]. Proceedings of the National Academy of Sciences, 2016, 11 1: 11865-11870. DOI: 10.1073/pnas.1609019113

2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one Preparation Products And Raw materials

Raw materials

Preparation Products

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2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one Suppliers

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View Lastest Price from 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one manufacturers

Career Henan Chemical Co
Product
2-[2-ethoxy-4-(4-hydroxypiperidin-1-yl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one 1234480-50-2
Price
US $1.00/KG
Min. Order
1KG
Purity
Min98% HPLC
Supply Ability
g/kg/ton
Release date
2020-01-01

1234480-50-2, 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-oneRelated Search:

6H-PyriMido[4,5-b][1,4]benzodiazepin-6-one, 5,11-dihydro-2-[[2-Methoxy-4-(4-Methyl-1-piperazinyl)phenyl]aMino]-5,11-diMethyl- 3-METHOXYPIPERIDINE 4-Hydroxypiperidine 3-Hydroxypiperidine XMD17-51 ACK1-B19 XMD17 109 XMD-17-51 Trifluoroacetate XMD16-5 BIX 02189 Trametinib Sunitinib Malate BEZ235 (NVP-BEZ235, Dactolisib) Y-27632 dihydrochloride LY 294002 Hydrochloride 6H-Pyrimido[4,5-b][1,4]benzodiazepin-6-one, 5,11-dihydro-5,11-dimethyl-2-[[1-(4-piperidinyl)-1H-pyrazol-4-yl]amino]-, 2,2,2-trifluoroacetate (1:1) 6H-Pyrimido[4,5-b][1,4]benzodiazepin-6-one, 2-[[2-ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-, 2,2,2-trifluoroacetate (1:1)

  • 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one
  • 2-((2-ethoxy-4-(4-hydroxypiperidin-1-yl)phenyl)amino)-5,11-dimethyl-5H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6(11H)-one
  • 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one XMD 8-92
  • XMD 8-92 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one
  • 2-[2-ethoxy-4-(4-hydroxypiperidin-1-yl)anilino]-5,11-dimethylpyrimido[4,5-b][1,4]benzodiazepin-6-one
  • XMD 8-92 trifluoroacetate
  • 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4
  • XMD 8-92
  • XMD 8-92 (free base)
  • CS-641
  • 6H-Pyrimido[4,5-b][1,4]benzodiazepin-6-one, 2-[[2-ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-
  • XMD8-92 >=98% (HPLC)
  • 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidinyl)phenyl]amino]-5,11-dihydro-5,11-dimethyl-6H-pyrimido[4,5-b][1,4]benzodiazepin-6-one USP/EP/BP
  • 2-((2-Ethoxy-4-(4-hydroxypiperidin-1-yl)phenyl)amino)-5,11-dimethyl-5,11-dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one
  • 2-[[2-Ethoxy-4-(4-hydroxy-1-piperidyl)phenyl]amino]-5,11-dimethyl-5H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6(11H)-one
  • XMD8-92, 10 mM in DMSO
  • XMD8-92 ，S7525
  • 1234480-50-2
  • Inhibitors