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Merck

363960

Sigma-Aldrich

(S,R)-诺司卡品

97%

别名:

α-Narcotine, (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone

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About This Item

经验公式(希尔记法):
C22H23NO7
CAS号:
分子量:
413.42
EC 号:
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

质量水平

方案

97%

表单

solid

旋光性

[α]20/D −200°, c = 1 in chloroform

mp

174-176 °C (lit.)

官能团

ester

SMILES字符串

COc1ccc2C(OC(=O)c2c1OC)C3N(C)CCc4cc5OCOc5c(OC)c34

InChI

1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

InChI key

AKNNEGZIBPJZJG-MSOLQXFVSA-N

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一般描述

(S,R)-Noscapine is a phthalideisoquinoline alkaloid found in opium. It is an antimicrotubule agent that also shows potent antitumor activity.

应用

Noscapine may be used as a source to synthesize its bromo-derivatives, which has higher tubulin binding activity when compared to noscapine. Its 3,4,5-trimethoxybenzyl analog is a potential antitumor agent.

象形图

Exclamation mark

警示用语:

Warning

危险声明

预防措施声明

危险分类

Acute Tox. 4 Oral - STOT SE 3

靶器官

Central nervous system

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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V Pannu et al.
Cell death & disease, 3, e346-e346 (2012-07-13)
Centrosome amplification (CA) and resultant chromosomal instability have long been associated with tumorigenesis. However, exacerbation of CA and relentless centrosome declustering engender robust spindle multipolarity (SM) during mitosis and may induce cell death. Recently, we demonstrated that a noscapinoid member
Zhong-Ze Fang et al.
British journal of pharmacology, 167(6), 1271-1286 (2012-06-08)
Noscapine is a promising anti-tumour agent. The purpose of the present study was to describe the metabolic map and investigate the bioactivation of noscapine. Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight mass spectrometry-based metabolomics was used to analyse
Pradeep K Naik et al.
Journal of computer-aided molecular design, 25(5), 443-454 (2011-05-06)
Noscapine and its derivatives are important microtubule-interfering agents shown to have potent anti-tumor activity. The binding free energies (ΔG (bind)) of noscapinoids computed using linear interaction energy (LIE) method with a surface generalized Born (SGB) continuum solvation model were in
Niyati Jhaveri et al.
Cancer letters, 312(2), 245-252 (2011-09-20)
Noscapine, a common oral antitussive agent, has been shown to have potent antitumor activity in a variety of cancers. Treatment of glioblastoma multiforme (GBM) with temozolomide (TMZ), its current standard of care, is problematic because the tumor generally recurs and
Thilo Winzer et al.
Science (New York, N.Y.), 336(6089), 1704-1708 (2012-06-02)
Noscapine is an antitumor alkaloid from opium poppy that binds tubulin, arrests metaphase, and induces apoptosis in dividing human cells. Elucidation of the biosynthetic pathway will enable improvement in the commercial production of noscapine and related bioactive molecules. Transcriptomic analysis

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