ChemicalBook > CAS DataBase List > N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine

N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine

Product Name
N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine
CAS No.
1097917-15-1
Chemical Name
N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine
Synonyms
AS3026;CS-286;ASP 3026;ASP3026 ，S8054;ASP 3026; ASP-3026;ASP3026, 10 mM in DMSO;ASP3026;ASP 3026;ASP-3026;N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfon;N2-(2-(isopropylsulfonyl)phenyl)-N4-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)-1,3,5-triazine-2,4-diamine;2-N-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-4-N-(2-propan-2-ylsulfonylphenyl)-1,3,5-triazine-2,4-diamine
CBNumber
CB62589620
Molecular Formula
C29H40N8O3S
Formula Weight
580.74
MOL File
1097917-15-1.mol
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N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine Property

Boiling point:
794.3±70.0 °C(Predicted)
Density 
1.276
storage temp. 
Store at -20°C
solubility 
insoluble in H2O; ≥14.53 mg/mL in DMSO; ≥4.9 mg/mL in EtOH with gentle warming and ultrasonic
form 
solid
pka
8.14±0.42(Predicted)
color 
White to off-white
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
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N-Bromosuccinimide Price

Cayman Chemical
Product number
18491
Product name
ASP3026
Purity
≥98%
Packaging
1mg
Price
$39
Updated
2024/03/01
Cayman Chemical
Product number
18491
Product name
ASP3026
Purity
≥98%
Packaging
5mg
Price
$96
Updated
2024/03/01
Cayman Chemical
Product number
18491
Product name
ASP3026
Purity
≥98%
Packaging
10mg
Price
$152
Updated
2024/03/01
Cayman Chemical
Product number
18491
Product name
ASP3026
Purity
≥98%
Packaging
25mg
Price
$331
Updated
2024/03/01
Tocris
Product number
5310
Product name
ASP3026
Purity
≥99%(HPLC)
Packaging
10
Price
$185
Updated
2021/12/16
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N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine Chemical Properties,Usage,Production

Description

ASP3026 is an ATP-competitive, second-generation ALK inhibitor (IC50 = 3.5 nM) that also inhibits ROS (IC50 = 8.9 nM) and ACK (IC50 = 5.8 nM). It inhibits neuroblastoma-activating ALK mutants F1174L (IC50 = 10 nM) and R1275Q (IC50 = 5.4 nM) and demonstrates antitumor activity in xenograft mouse models. ASP3026 has been shown to overcome crizotinib resistance in non-small cell lung cancer, and is currently being evaluated in clinical trials of patients with ALK-positive solid tumors.

Uses

ASP3026 is a novel and selective anaplastic lymphoma kinase (ALK) inhibitor that shows potent anti-tumor activities. ASP3026 also shows potential efficacy for non-small cell lung cancer (NSCLC) and is expected to improve the therapeutic outcomes of patients with cancer with ALK abnormality. Potent ALK inhibitor.

Definition

ChEBI: ASP-3026 is a member of the class of diamino-1,3,5-triazines that is 1,3,5-triazine-2,4-diamine in which the amino groups at positions 2 and 4 are respectively carrying 2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl and 2-(propan-2-ylsulfonyl)phenyl substituents. It is a potent inhibitor of anaplastic lymphoma kinase (ALK), Ack and ROS1 activity (IC50 values are 3.5, 5.8 and 8.9 nM respectively) and exhibits anti-cancer properties. It has a role as an antineoplastic agent, an apoptosis inducer, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor, an antimalarial and an EC 6.1.1.6 (lysine--tRNA ligase) inhibitor. It is a secondary amino compound, a monomethoxybenzene, a N-methylpiperazine, an aromatic amine, a diamino-1,3,5-triazine, a member of piperidines and a sulfone.

Synthesis

109-01-3

1097917-68-4

1097917-15-1

Alternative to Step 7, Method 2 (Example of using a reducing catalyst): Synthesis of N-{2-methoxy-4-[4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}-N'-[2-(propane-2-sulfonyl)phenyl]-1 ,3,5-triazine-2,4-diamine (compounds of formula (1)). 1-[3-Methoxy-4-({4-[2-(propane-2-sulfonyl)anilino]-1,3,5-triazin-2-yl}amino)phenyl]piperidin-4-one (5.0 g), tetrahydrofuran (30 mL), N-methylpiperazine (1.81 g), and 10% palladium-carbon (~50% wet product, 0.8 g) were mixed. The mixture was stirred at 40°C for 7 hours under a hydrogen atmosphere (2.4821 x 10^5 Pa). Upon completion of the reaction, the palladium carbon was removed by filtration and washed with tetrahydrofuran (10 mL). The combined filtrates were concentrated under reduced pressure. To the concentrated residue was added 2-butanone (9 mL) and the resulting mixture was stirred at 60°C for 30 minutes and then slowly cooled to 30°C. After addition of n-heptane (9 mL), the mixture was stirred at room temperature for 19 h. The precipitated crystals were collected by filtration. The crystals were washed with a mixture of 2-butanone (1 mL) and n-heptane (1 mL) and then dried under reduced pressure at 40 °C to afford the target product N-{2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}-N'-[2-(propane-2-sulfonyl)phenyl]-1,3,5-triazine-2,4-diamine (3.09 g, yield 88.0%). Nuclear magnetic resonance hydrogen spectroscopy (1H NMR) data: δ 1.31 (6H, d, J = 6.8Hz), 1.59-1.78 (2H, m), 1.90-2.01 (2H, m), 2.24-2.80 (11H, m), 2.30 (3H, s), 3.19-3.32 (1H, m), 3.65-3.75 (2H, m), 3.88 (3H, m). 3.88 (3H, s), 6.50-6.59 (2H, m), 7.18-7.30 (1H, m), 7.53-7.70 (2H, m), 7.88 (1H, dd, J = 1.5, 8.3Hz), 8.10 (1H, br), 8.37 (1H, br), 8.53 (1H, br), 9.29 (1H, s). Mass spectrum (ESI+): m/z 581.

in vivo

ASP3026 (30 mg/kg daily for 10 weeks, p.o.) inhibits the growth of NPM-ALK+ ALCL tumor cells in mice[2].
ASP3026 (10 mg/kg daily for 5 days, p.o.) can enhance the antitumor activity of Paclitaxel (HY-B0015) and Pemetrexed (HY-10820). When used alone, it can induce tumor regression and prolong survival in non-small cell lung cancer model mice, and does not affect the body weight of non-small cell lung cancer model mice[4].

Animal Model:Female C.B-17 SCID mice of systemic xenograft lymphoma model[2]
Dosage:30 mg/kg daily for 10 weeks
Administration:p.o.
Result:Mice in the ASP3026-interrupted group developed recurrent lymphoma, were subsequently treated with ASP3026 and survived until the end of the study.

IC 50

ROS; ACK; Caspase-3; PARP1; IGF-1R; STAT3

storage

Store at -20°C

References

[1] kuromitsu s, mori m, shimada i, et al. anti-tumor activity of asp3026, a novel and selective alk inhibitor of anaplastic lymphoma kinase (alk).annual meeting of the american association for cancer research (aacr), orlando, fl. 2011.
[2] mori m, ueno y, konagai s, et al. the selective anaplastic lymphoma receptor tyrosine kinase inhibitor asp3026 induces tumor regression and prolongs survival in non–small cell lung cancer model mice. molecular cancer therapeutics, 2014, 13(2): 329-340.
[3] george s k, vishwamitra d, manshouri r, et al. the alk inhibitor asp3026 eradicates npm-alk+ t-cell anaplastic large-cell lymphoma in vitro and in a systemic xenograft lymphoma model. oncotarget, 2014, 5(14): 5750-5763.

N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine Preparation Products And Raw materials

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View Lastest Price from N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine manufacturers

Career Henan Chemical Co
Product
N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine 1097917-15-1
Price
US $1.00/KG
Min. Order
1KG
Purity
95-99%
Supply Ability
1ton
Release date
2019-12-31

1097917-15-1, N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamineRelated Search:

Ceritinib Alectinib ALK/IGF1R inhibitor AP26113 Crizotinib Lorlatinib (PF-06463922) AGI6780 CC0651 6-Amino-8-[(6-iodo-1,3-benzodioxol-5-yl)thio]-N-(1-methylethyl)-9H-purine-9-propanamine IDO-IN-7 UNC 0631 XL 228 N-(3-Chlorophenyl)-N'-[5-[2-(thieno[3,2-d]pyrimidin-4-ylamino)ethyl]-2-thiazolyl]urea SGI 7079 Gilteritinib N-(1,1-Dimethylethyl)-3-[[5-methyl-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-4-pyrimidinyl]amino]benzenesulfonamide ABX-1431 UNC2541

  • ASP 3026; ASP-3026
  • CS-286
  • ASP3026;ASP 3026;ASP-3026
  • N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfon
  • N2-(2-(isopropylsulfonyl)phenyl)-N4-(2-methoxy-4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)-1,3,5-triazine-2,4-diamine
  • ASP 3026
  • N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine
  • 1,3,5-Triazine-2,4-diamine, N2-[2-methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-
  • N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine ASP 3026
  • N2-[2-Methoxy-4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-1,3,5-triazine-2,4-diamine USP/EP/BP
  • AS3026
  • ASP3026, 10 mM in DMSO
  • ASP3026 ，S8054
  • 2-N-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-4-N-(2-propan-2-ylsulfonylphenyl)-1,3,5-triazine-2,4-diamine
  • 1097917-15-1
  • C29H40N8O3S
  • Inhibitors