363960
(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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关于此项目
经验公式（希尔记法）:
C22H23NO7
化学文摘社编号:
分子量:
413.42
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
EC Number:
204-899-2
MDL number:
Assay:
97%
Form:
solid
InChI key
AKNNEGZIBPJZJG-MSOLQXFVSA-N
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
SMILES string
COc1ccc2C(OC(=O)c2c1OC)C3N(C)CCc4cc5OCOc5c(OC)c34
assay
97%
form
solid
optical activity
[α]20/D −200°, c = 1 in chloroform
mp
174-176 °C (lit.)
functional group
ester
General description
(S,R)-Noscapine is a phthalideisoquinoline alkaloid found in opium. It is an antimicrotubule agent that also shows potent antitumor activity.
Application
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.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Acute Tox. 4 Oral - STOT SE 3
target_organs
Central nervous system
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
法规信息
新产品
此项目有
Laleh Alisaraie et al.
Chemical biology & drug design, 78(4), 535-546 (2011-07-26)
Noscapine, the benzylisoquinoline alkaloid, 5-(4,5-Dimethoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium, has been extensively used as a cough-suppressing medication with low toxicity. It has been recently shown to also have anti-cancer activity in mice and humans. In this work, using in silico analyses, the most probable
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
Thu-Thuy T Dang et al.
Plant physiology, 159(2), 618-631 (2012-04-27)
Noscapine is a benzylisoquinoline alkaloid produced in opium poppy (Papaver somniferum) and other members of the Papaveraceae. It has been used as a cough suppressant and more recently was shown to possess anticancer activity. However, the biosynthesis of noscapine in
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
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