所有图片(1)
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
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
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质量水平
检测方案
97%
形式
solid
旋光性
[α]20/D −200°, c = 1 in chloroform
mp
174-176 °C (lit.)
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.
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
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
法规信息
新产品
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
Brominated derivatives of noscapine are potent microtubule-interfering agents that perturb mitosis and inhibit cell proliferation.
Zhou J, et al.
Molecular Pharmacology, 63(4), 799-807 (2003)
Pradeep K Naik et al.
Journal of computer-aided molecular design, 26(2), 233-247 (2011-12-16)
Our screen for tubulin-binding small molecules that do not depolymerize bulk cellular microtubules, but based upon structural features of well known microtubule-depolymerizing colchicine and podophyllotoxin, revealed tubulin binding anti-cancer property of noscapine (Ye et al. in Proc Natl Acad Sci
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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