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Merck

SML2671

Sigma-Aldrich

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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About This Item

经验公式(希尔记法):
C18H18ClF5N6O · C4H4O4
分子量:
580.89
MDL编号:
UNSPSC代码:
41116004
NACRES:
NA.77

方案

≥98% (HPLC)

表单

powder

储存条件

desiccated

颜色

white to beige

溶解性

DMSO: 2 mg/mL, clear
H2O: 5 mg/mL

储存温度

−20°C

SMILES字符串

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

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

InChI key

TUXZQBYIZLWUKK-AFIAKLHKSA-N

生化/生理作用

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

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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
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
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

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