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
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
Jitender Madan et al.
Molecular pharmaceutics, 9(5), 1470-1480 (2012-05-01)
We have previously shown that a novel microtubule-modulating noscapinoid, EM011 (9-Br-Nos), displays potent anticancer activity by inhibition of cellular proliferation and induction of apoptosis in prostate cancer cells and preclinical mice models. However, physicochemical and cellular barriers encumber the development
Cloning and characterization of canadine synthase involved in noscapine biosynthesis in opium poppy.
Thu-Thuy T Dang et al.
FEBS letters, 588(1), 198-204 (2013-12-10)
Noscapine biosynthesis in opium poppy is thought to occur via N-methylcanadine, which would be produced through 9-O-methylation of (S)-scoulerine, methylenedioxy bridge formation on (S)-tetrahydrocolumbamine, and N-methylation of (S)-canadine. Only scoulerine 9-O-methyltransferase has been functionally characterized. We report the isolation and
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
Discovery of S-phase arresting agents derived from noscapine.
Anderson JT, et al.
Journal of Medicinal Chemistry, 48(8), 2756-2758 (2005)
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