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Merck
CN

SML2671

Cevipabulin fumarate

≥98% (HPLC)

别名:

5-Chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-N-((1S)-2,2,2-trifluoro-1-methylethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine fumarate, 5-Chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine, TTI-237 fumarate

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关于此项目

经验公式（希尔记法）:
C18H18ClF5N6O · C4H4O4
化学文摘社编号:
849550-67-0
分子量:
580.89
UNSPSC Code:
41116004
NACRES:
NA.77
MDL number:
MFCD31813783

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InChI

1S/C18H18ClF5N6O.C4H4O4/c1-9(18(22,23)24)28-16-14(15(19)29-17-26-8-27-30(16)17)13-11(20)6-10(7-12(13)21)31-5-3-4-25-2;5-3(6)1-2-4(7)8/h6-9,25,28H,3-5H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t9-;/m0./s1

SMILES string

FC1=CC(OCCCNC)=CC(F)=C1C2=C(N[C@@H](C)C(F)(F)F)N3C(N=C2Cl)=NC=N3.O=C(/C=C/C(O)=O)O

InChI key

TUXZQBYIZLWUKK-AFIAKLHKSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear, H2O: 5 mg/mL

storage temp.

−20°C

相关类别

Biochem/physiol Actions

Cevipabulin (TTI-237) is a potent microtubule-stabilizing agent that binds to tubulin vinblastine binding site, a typical site of binding for microtubule-destabilizing agents. It is likely that cevipabulin, similarly to other triazolopyrimidines, promotes longitudinal tubulin contacts in microtubules, which promotes stabilization of micro-tubule. Cevipabulin exhibits potent cytotoxic activity in cancer cell lines including cell line expressing a high level of P-glycoprotein. It is active in vivo in several mouse xenograft models of human cancer.
potent microtubule-stabilizing agent that binds to tubulin vinblastine binding site

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000080086
0000080087
0000075031

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Gonzalo Sáez-Calvo et al.
Cell chemical biology, 24(6), 737-750 (2017-06-06)
Microtubule-targeting agents (MTAs) are some of the clinically most successful anti-cancer drugs. Unfortunately, instances of multidrug resistances to MTA have been reported, which highlights the need for developing MTAs with different mechanistic properties. One less explored class of MTAs are [1,2,4]triazolo[1,5-a]pyrimidines
Jane Kovalevich et al.
The Journal of pharmacology and experimental therapeutics, 357(2), 432-450 (2016-03-17)
The microtubule (MT)-stabilizing protein tau disengages from MTs and forms intracellular inclusions known as neurofibrillary tangles in Alzheimer's disease and related tauopathies. Reduced tau binding to MTs in tauopathies may contribute to neuronal dysfunction through decreased MT stabilization and disrupted
Carl F Beyer et al.
Cancer research, 68(7), 2292-2300 (2008-04-03)
5-Chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine butanedioate (TTI-237) is a microtubule-active compound of novel structure and function. Structurally, it is one of a class of compounds, triazolo[1,5a]pyrimidines, previously not known to bind to tubulin. Functionally, TTI-237 inhibited the binding of [(3)H]vinblastine to tubulin, but it

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