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Merck
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重要文件

363960

Sigma-Aldrich

(S,R)-诺司卡品

97%

同義詞:

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

經驗公式(希爾表示法):
C22H23NO7
CAS號碼:
分子量::
413.42
EC號碼:
MDL號碼:
分類程式碼代碼:
12352005
PubChem物質ID:
NACRES:
NA.22
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品質等級

化驗

97%

形狀

solid

光學活性

[α]20/D −200°, c = 1 in chloroform

mp

174-176 °C (lit.)

官能基

ester

SMILES 字串

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 密鑰

AKNNEGZIBPJZJG-MSOLQXFVSA-N

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一般說明

(S,R)-Noscapine is a phthalideisoquinoline alkaloid found in opium. It is an antimicrotubule agent that also shows potent antitumor activity.[1]

應用

Noscapine may be used as a source to synthesize its bromo-derivatives, which has higher tubulin binding activity when compared to noscapine.[1] Its 3,4,5-trimethoxybenzyl analog is a potential antitumor agent.[2]

象形圖

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訊號詞

Warning

危險聲明

防範說明

危險分類

Acute Tox. 4 Oral - STOT SE 3

標靶器官

Central nervous system

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


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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
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
Pradeep K Naik et al.
Journal of molecular graphics & modelling, 29(7), 947-955 (2011-05-03)
We have previously discovered the tubulin-binding anti-cancer properties of noscapine and its derivatives (noscapinoids). Here, we present three lines of evidence that noscapinoids bind at or near the well studied colchicine binding site of tubulin: (1) in silico molecular docking
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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