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Merck
CN

A1882

Sigma-Aldrich

6-氮杂尿苷

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别名:
2-β-D-呋核亚硝脲-1,2,4-三嗪-3,5(2H,4H)-二酮, 6-氮嘧啶核苷
经验公式(希尔记法):
C8H11N3O6
CAS号:
分子量:
245.19
EC 号:
MDL编号:
UNSPSC代码:
41106305
PubChem化学物质编号:
NACRES:
NA.51

检测方案

≥99% (TLC)

质量水平

形式

powder

mp

157-159 °C (lit.)

溶解性

water: 50 mg/mL, clear, colorless

储存温度

2-8°C

SMILES字符串

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC(=O)NC2=O

InChI

1S/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)/t3-,5-,6-,7-/m1/s1

InChI key

WYXSYVWAUAUWLD-SHUUEZRQSA-N

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一般描述

6-氮杂尿苷是嘧啶核苷类似物。

应用

6-氮杂尿苷已用于:
  • 用于尿苷一磷酸合酶(UMPS)活性测定
  • 作为抗病毒药物,研究其对足口病病毒的抑制效应和细胞毒活性
  • 筛选抗隐孢子虫活性
  • 对HeLa细胞进行预处理,以研究捕获5-溴尿苷5′-三磷酸(BrUTP)前和捕获过程中抑制细胞尿苷合成的效应
  • 用作参照化合物,比较其对病毒宿主细胞株的抗病毒活性和细胞毒活性

6-氮杂尿苷(AzUrd)阻止乳清酸转化为UMP,并用于抗病毒研究。

生化/生理作用

6-氮杂尿苷是一种前药,在转化为6-氮杂-UMP后会抑制尿苷单磷酸合酶(UMPS)。它是一种广谱的抗代谢药。它干扰嘧啶的生物合成并影响细胞核酸水平。它被认为是一种抗肿瘤代谢物。它抑制基孔肯雅病毒、塞姆利基森林病毒和人类冠状病毒等RNA病毒。它显著抑制隐孢子虫寄生虫的生长。

象形图

Health hazardExclamation mark

警示用语:

Warning

危险分类

Acute Tox. 4 Oral - Carc. 2

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


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Donald F Smee et al.
Journal of virological methods, 246, 51-57 (2017-04-01)
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Takashi Kobayashi et al.
Physical chemistry chemical physics : PCCP, 12(19), 5140-5148 (2010-05-07)
Excited state characteristics of 6-azauridine (6AUd), which is known as a medicine against psoriasis and neoplastic, were investigated with laser plash photolysis, time-resolved thermal lensing, and near IR single photon counting method. The triplet-triplet absorption spectrum of 6AUd was observed
S Bhasin et al.
The American journal of physiology, 243(3), E234-E239 (1982-09-01)
Ketonemic states complicating late pregnancy are accompanied by lower brain weights in the newborn. Potential mechanisms whereby ketone bodies might inhibit cell proliferation were therefore examined in the fetal rat brain slice by measuring their impact on the de novo
Jean Marc Crance et al.
Antiviral research, 58(1), 73-79 (2003-04-30)
Ribavirin, interferon-alpha (IFN-alpha), 6-azauridine and glycyrrhizin were tested in vitro for their antiviral activities against 11 pathogenic flaviviruses belonging to principal antigenic complexes or individual serogroups of medical importance: dengue, Japanese encephalitis, mammalian tick-borne and yellow fever virus (YFV) groups.

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