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质量水平
方案
≥98% (HPLC)
表单
powder
旋光性
[α]/D -980 to -1015 (C=1, MeOH)
颜色
yellow
溶解性
DMSO: ≥25 mg/mL
储存温度
2-8°C
SMILES字符串
O=C1O[C@@]23C[C@@H](C=CC2=C1)N4CCCC[C@H]34
InChI
1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1
InChI key
SWZMSZQQJRKFBP-WZRBSPASSA-N
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应用
Securinine was used as a standard in the synthesis of the members of Securinega alkaloid family.
生化/生理作用
Securinine is an alkaloid widely in traditional folk medicine. Long known as a GABAA antagonist, securinine was recently found to up-regulate p53 protein and to modulate the related family member p73 protein in a p53-dependent fashion, inducing p73 in the HCT116 p53(-) cells and down-regulating it in the p53(+) cells. Induction of proapoptotic protein p73 only in p53 cells could be used to target cancer cells preferentially. Securinine has been found to induce p53-independent, p73-dependent apoptosis in RKO colon cancer cells.
特点和优势
This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
警示用语：
Danger
危险声明
危险分类
Acute Tox. 3 Oral
储存分类代码
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
法规信息
新产品
Jung-Hsuan Chen et al.
Organic letters, 14(17), 4531-4533 (2012-08-24)
Total syntheses of (±)-securinine and (±)-allosecurinine that employ a tandem rhodium carbenoid-initiated Claisen/α-ketol rearrangement sequence as a key step are described.
S Liras et al.
Organic letters, 3(5), 703-706 (2001-03-22)
[structure: see text]. The concise total synthesis of securinine in nine steps from readily available starting materials is described. Key steps of the synthesis include an addition of a silyloxyfuran to an in situ generated iminium ion and a novel
Gisela G Bardají et al.
The Journal of organic chemistry, 73(19), 7657-7662 (2008-09-11)
A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has
Matt Shipman et al.
PloS one, 7(9), e41278-e41278 (2012-10-03)
Securinine, a GABA(A) receptor antagonist, has been reported to enhance monocyte cell killing of Coxiella burnetii without obvious adverse effects in vivo. We employed multiplex 2D gel electrophoresis using Zdyes, a new generation of covalently linked fluorescent differential protein detection
D Raj et al.
Fitoterapia, 79(6), 419-427 (2008-06-07)
This review gives an account of the current knowledge on the chemical constituents, biological activity and pharmacological properties of Securinega suffruticosa. A wide range of chemical compounds have been isolated, mainly alkaloids, flavonoids, tannins and lipids. From the pharmacological point
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