2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one

• ChemBase编号: 73249
• 分子式: C9H13N5O4
• 平均质量: 255.23062
• 单一同位素质量: 255.09675392
• SMILES: [nH]1c(nc2c(c1=O)ncn2COC(CO)CO)N
• Canonical SMILES: OCC(OCn1cnc2c1nc(N)[nH]c2=O)CO
• InChI: InChI=1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)
• InChIKey: IRSCQMHQWWYFCW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one
• IUPAC传统名: @ganciclovir; gancyclovir; 2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one
• 别名: 2-Amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one; 2'-NDG; 2'-Nor-2'-deoxyguanosine; 9-(1,3-Dihydroxy-2-propoxymethyl)guanine; BW 759; BW 759U; BW-B 759U; Biolf 62; DHPG; Denosine; Gancyclovir; Ganguard; Ganquard; HHEMG; Hydroxyacyclovir; Natclovir; RS 21592; Vitrasert; Ganciclovir; Cytovene; Ganciclovir; 2-amino-9-(((1,3-dihydroxypropan-2-yl)oxy)methyl)-1H-purin-6(9H)-one

登记号

• CAS号: 82410-32-0
• MDL号: MFCD00870588
• PubChem SID: 162038169; 24278453
• PubChem CID: 3454

理论计算性质

• Acid pKa: 10.159807
• 质子受体: 7
• 质子供体: 4
• LogD (pH = 5.5): -2.1799848
• LogD (pH = 7.4): -2.1805685
• Log P: -2.1799026
• 摩尔折射率: 61.0293 cm^3
• 极化性: 22.50675 Å^3
• 极化表面积: 134.99 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 0.1 M HCl: soluble10 mg/mL; DMSO; Hot Methanol; Hot Water
• 外观: white powder; White Solid
• 熔点: 251-252°C
• 紫外吸收波长: ε1mM/256 nm 12.0

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: MF8407000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 46-60-61
• 安全公开号: 53-36/37/39-45
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H360
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 保存温度: 2-8°C

药理学性质

• 生物活性机理: Inhibitor of viral-DNA-synthesis

产品相关信息

• 纯度: ≥99% (HPLC); 97%
• 成盐信息: Free Base
• 应用领域: Active against herpes simplex virus types 1 and 2; Administered (ivn) in treatment of cytomegalovirus; Antiviral agent
• 产品质量级别: PREMIUM

详细说明

Selleck Chemicals - S1878

Research Area: Infection
Biological Activity:

Sigma Aldrich - G2536

Application
Ganciclovir is used in molecular biology for selection against random recombination events when homologous recombination of a gene of interest is required.
Biochem/physiol Actions
Ganciclovir is a pro-drug nucleoside analog that is activated by phosphorylation. It is useful in the study of gene therapy in cancer research.Upon expression of a viral suicide gene encoding thymidine kinase, the non-toxic pro-drug is converted to a phosphorylated active analog and is incorporated into the DNA of replicating eukaryotic cells, causing death of the malignant dividing cell.1 The cell cycle is irreversibly arrested at the G2-M checkpoint.2 Gap junction involvement in the ganciclovir bystander effect has been studied.3 Ganciclovir has been used to study loss of telomeres4 and to evaluate sensitivity of viruses to antiviral treatments.5

Toronto Research Chemicals - G235000

Ganciclovir is a nucleoside analog structurally related to Acyclovir (A192400). Ganciclovir is an antiviral.

参考文献

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