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Tozasertib

Product Name
Tozasertib
CAS No.
639089-54-6
Chemical Name
Tozasertib
Synonyms
VE465;VX 680;VE 465;CS-176;VE-465;VX-860;MK 0457;Tozasertib;L-001281814;VX-680/MK-0457
CBNumber
CB51513746
Molecular Formula
C23H28N8OS
Formula Weight
464.59
MOL File
639089-54-6.mol
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Tozasertib Property

Melting point:
248-253°C (dec.)
Density 
1.40±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 100 mg/ml).
form 
powder
pka
14.09±0.70(Predicted)
color 
white to beige
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
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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

Sigma-Aldrich
Product number
SML2158
Product name
VX-680
Purity
≥98% (HPLC)
Packaging
10mg
Price
$73.8
Updated
2025/07/31
Cayman Chemical
Product number
13600
Product name
MK-0457
Purity
≥98%
Packaging
25mg
Price
$86
Updated
2024/03/01
Cayman Chemical
Product number
13600
Product name
MK-0457
Purity
≥98%
Packaging
50mg
Price
$161
Updated
2024/03/01
Cayman Chemical
Product number
13600
Product name
MK-0457
Purity
≥98%
Packaging
100mg
Price
$302
Updated
2024/03/01
Cayman Chemical
Product number
13600
Product name
MK-0457
Purity
≥98%
Packaging
250mg
Price
$546
Updated
2024/03/01
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Tozasertib Chemical Properties,Usage,Production

Description

The Aurora kinases (A, B, and C) are a family of serine-threonine kinases that regulate various stages of mitotic function. With significant roles in cell cycle and cell division, Aurora kinase gene amplification and overexpression are linked to tumorigenesis. MK-0457 is a potent pan-Aurora kinase inhibitor but favors Aurora A (Ki = 0.6 nM) over Aurora B (Ki = 18 nM) or Aurora C (Ki = 4.6 nM). It shows selectivity against a panel of more than 190 different protein kinases. MK-0457 effectively inhibits proliferation of several different cell lines of clear cell renal carcinoma (IC50s = <10 μM) and blocks the growth of tumors in a rodent model of cancer (80 mg/kg), inhibiting histone H3 phosphorylation and increasing apoptosis. By depleting Aurora activity, MK-0457 disrupts bipolar spindle formation during mitosis, arresting cell cycle progression at the G2/M phase.

Chemical Properties

White Solid

Uses

Tozasertib is used as a multikinase inhibitor once used for cancer treatment.

Definition

ChEBI: N-[4-[[4-(4-methyl-1-piperazinyl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]-2-pyrimidinyl]thio]phenyl]cyclopropanecarboxamide is a N-arylpiperazine.

Biochem/physiol Actions

VX-680 is an ATP site-targeting potent aurora kinase inhibitor (Aurara A/B/C Ki(app) = 0.6/18/4.6 nM) that affects FLT3, BCR-Abl, BCR-Abl (T315I), Lck, ITK, Src, and Fyn only at higher concentrations (Ki(app) = 30, 30, 42, 80, 220, 350, 520 nM, respectively) and exhibits little inhibitory potency toward 52 other kinases (Ki(app) >1 μM). VX-680 exhibits potent antiproliferation activity in a wide variety of cancer cultures (IC50 from 15 to 113 nM) as a result of cell cycle arrest and apoptosis induction, as well as causes tumor retardation (by 98% on day 13; 75 mg/kg b.i.d i.p.; HL-60 in mice) and regression (2 mg/kg/h 3 d/wk i.v. infusion; HCT116 in rats) in vivo. Crystallography data reveal a tight association of VX-680 with a hydrophobic pocket present only in a closed, inactive kinase conformation, which forms the basis of its selectivity profile, including its activity toward wild-type and the Imatinib-resistant (T315I) Abl.

Synthesis

109-01-3

639090-55-4

639089-54-6

General synthesis of N-(4-((4-((4-((5-methyl-1H-pyrazol-3-yl)amino)-6-(4-methylpiperazin-1-yl)pyrimidin-2-yl)sulfanyl)phenyl)aminocyclopropanecarboxylic acid) and N-[4-[[4-chloro-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl]sulfanyl]phenyl]aminocyclopropane carboxylic acid as the raw materials The procedure was as follows: N-methylpiperazine (10 mL) was added to compound D (2.373 g, 5.92 mmol) and the reaction mixture was stirred at 110°C for 2 hours. Upon completion of the reaction, the excess N-methylpiperazine was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate, washed sequentially with aqueous sodium bicarbonate and dried over magnesium sulfate, and subsequently concentrated. The resulting residue was purified by methanol crystallization to afford colorless crystals of target product I (1.82 g, 66% yield). The product was characterized by 1H-NMR (DMSO-d6) with chemical shifts δ of 0.81 (4H, d), 1.79 (1H, m), 2.01 (3H, s), 2.18 (3H, s), 2.30 (4H, m), 3.35 (masked signal), 5.42 (1H, s), 6.02 (1H, br s), 7.47 (2H, d), and 7.69 (2H, d), 9.22 (1H, s), 10.39 (1H, s), 11.69 (1H, s).

References

[1] ELIZABETH A HARRINGTON. VX-680, a potent and selective small-molecule inhibitor of the Aurora kinases, suppresses tumor growth in vivo[J]. Nature Medicine, 2004, 10 3: 262-267. DOI:10.1038/nm1003
[2] FEI FEI. Activity of the Aurora kinase inhibitor VX-680 against Bcr/Abl-positive acute lymphoblastic leukemias.[J]. Molecular Cancer Therapeutics, 2010: 1318-1327. DOI:10.1158/1535-7163.mct-10-0069
[3] ALEXANDER DEWERTH. In vitro evaluation of the Aurora kinase inhibitor VX-680 for Hepatoblastoma.[J]. Pediatric Surgery International, 2012: 579-589. DOI:10.1007/s00383-012-3086-6

Tozasertib Preparation Products And Raw materials

Raw materials

Preparation Products

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Tozasertib Suppliers

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View Lastest Price from Tozasertib manufacturers

Career Henan Chemical Co
Product
Tozasertib 639089-54-6
Price
US $1.00/g
Min. Order
100g
Purity
99%
Supply Ability
G/KG/T
Release date
2019-12-20

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  • Cyclopropane carboxylic acid {4-[4-(4-methyl-piperazin-1-yl)-6-(5-methyl-2H-pyrazol-3-ylamino) -pyrimidin-2ylsulphanyl]-phenyl}-amide
  • VX-680/MK-0457
  • N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-(1-methylpiperidin-4-ylamino)pyrimidin-2-ylthio)phenyl)cyclopropanecarboxamide
  • MK 0457
  • N-[4-[[4-(4-Methyl-1-piperazinyl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]-2-pyrimidinyl]thio]phenyl]cyclopropanecarboxamide
  • Tozasertib
  • VX 680
  • Cyclopropanecarboxamide, N-(4-((4-(4-methyl-1-piperazinyl)-6-((5-methyl-1H-pyrazol-3-yl)amino)-2-pyrimidinyl)thio)phenyl)-
  • VX680;MK0457;VX 680 (MK 0457;TOZASERTIB)
  • CS-176
  • VE 465
  • VE465
  • VE-465
  • VX680; VX 680; VX-680; MK0457; MK 0457; MK-0457; VE465; VE-465; VE 465; TOZASERTIB
  • TOZASERTIB;MK-0457;MK0457;VX680;VX 680;MK 0457
  • N-(4-(4-(5-Methyl-1H-pyrazol-3-ylamino)-6-(1-methylpiperidin-4-ylamino)pyrimidin-2-ylthio)phen
  • N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylthio)phenyl)cyclopropanecarboxamide
  • Tozasertib N-[4-[[4-(4-Methyl-1-piperazinyl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]-2-pyrimidinyl]thio]phenyl]cyclopropanecarboxamide
  • VX-680(Tozasertib)
  • Tozasertib(MK-0457,VX-680)
  • VX-860
  • N-[4-({4-[(3-METHYL-1H-PYRAZOL-5-YL)AMINO]-6-(4-METHYLPIPERAZIN-1-YL)PYRIMIDIN-2-YL}SULFANYL)PHENYL]CYCLOPROPANECARBOXAMIDE
  • tozasertib (MK-0457)
  • MK-0457,Tozasertib
  • Cyclopropanecarboxylic acid N-(4-((4-(4-methylpiperazin-1-yl)-6-(5-methyl-2H-pyrazol-3-ylamino)pyrimidin-2-yl)sulfanyl)phenyl)amide
  • L-001281814
  • Tozasertib/VX-680
  • N-(4-(4-(3-methyl-1H-pyrazol-5-ylamino)-6-(4-methylpiperazin-1-yl)pyrimidin-2-ylthio)phenyl)cyclopropanecarboxamide
  • VX-680 (MK-0457)(Tozasertib)
  • Tozasertib￡VX680￡MK0457
  • Tozasertib Free Base
  • N-[4-[[4-(4-Methylpiperazin-1-yl)-6-[(5-Methyl-1H-pyrazol-3-yl)aMino]pyriMidin-2-yl]thio]phenyl]cyclopropanecarboxaMide
  • VX-680 (Tozasertib, MK-0457)
  • Tozasertib USP/EP/BP
  • N-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]cyclopropanecarboxamide
  • MK-0457 Tozasertib VX-680
  • VX-680 (MK-0457), Aurora kinase inhibitor
  • Tozasertib, 10 mM in DMSO
  • N-[4-({4-[(5-methyl-1H-pyrazol-3-yl)amino]-6-(4-methylpiperazin-1-yl)pyrimidin-2-yl}sulfanyl)phenyl]cyclopropanecarboxamide
  • Tozasertib（639089-54-6）
  • 639089-54-6
  • C24H30N8OS
  • C23H28N8OS
  • Inhibitors
  • A multikinase inhibitor.
  • Inhibitor
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Mutagenesis Research Chemicals
  • Pharmaceuticals