1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase编号: 119449
• 分子式: C10H13N5O4
• 平均质量: 267.24132
• 单一同位素质量: 267.09675392
• SMILES: n1(c(=O)[nH]c(=O)c(c1)C)[C@@H]1O[C@@H]([C@H](C1)N=[N+]=[N-])CO
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1N=[N+]=[N-])n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
• InChIKey: HBOMLICNUCNMMY-XLPZGREQSA-N

名称和登记号

名称

• IUPAC标准名: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC传统名: 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione; zidovudine
• 别名: 叠氮胸苷; 齐多夫定; 3′-叠氮-3′-脱氧胸苷; 3'-Azido-3'-deoxythymidine; 3'-Azidothymidine; Apovir; Novo-AZT; Zidovir; Zidovudine; Zidovudine; Retrovis; Timazid; Retrovir; NSC 602670; 3'-Azido-3'-deoxythymidine; AZT; ZDV; 3′-Azido-3′-deoxythymidine; 1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione; 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

登记号

• CAS号: 30516-87-1
• MDL号: MFCD00006536
• Beilstein号: 3595791
• PubChem SID: 24278143; 162103188
• PubChem CID: 35370

理论计算性质

• Acid pKa: 9.960416
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.41276968
• LogD (pH = 7.4): -0.41393453
• Log P: -0.29870915
• 摩尔折射率: 61.7045 cm^3
• 极化性: 23.694994 Å^3
• 极化表面积: 108.3 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; H2O: soluble50 mg/mL; Methanol
• 外观: White to Off White Solid
• 熔点: 113-115 °C(lit.); 118-120°C; 122 - 124°C
• 疏水性(logP): 0.044

安全信息

• 保存条件: Refrigerator
• RTECS编号: XP2072000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351
• GHS警示性声明: P281
• 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: -20°C

药理学性质

• 相关基因信息: human ... HIVE1(3095)mouse ... Slc29a1(63959)
• 生物活性机理: Nucleoside transporter substrate; Reverse Transcriptase Inhibitor

产品相关信息

• 纯度: ≥98% (HPLC); 95%
• 应用领域: Antiviral agent active exclusively against retroviruses, esp. AIDS virus and leukaemias; Drugs of choice for AIDS treatment

详细说明

Sigma Aldrich - A2169

Biochem/physiol Actions
对 HIV-1 病毒有效的逆转录酶抑制剂。
包装
1 g in glass bottle
100, 250 mg in glass bottle
25 mg in poly bottle

Toronto Research Chemicals - A825000

A potent and selective inhibitor of HIV-1 replication.

参考文献

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• Wan, J., et al.: J. Med. Chem., 52, 1144 (1987)
• Mainardes, R., et al.: J. Pharm. Sci., 98, 257 (1987)
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