6-(benzyloxy)-9H-purin-2-amine

• ChemBase编号: 69988
• 分子式: C12H11N5O
• 平均质量: 241.24864
• 单一同位素质量: 241.09636
• SMILES: n1c[nH]c2c1nc(N)nc2OCc1ccccc1
• Canonical SMILES: Nc1nc(OCc2ccccc2)c2c(n1)nc[nH]2
• InChI: InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)
• InChIKey: KRWMERLEINMZFT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-(benzyloxy)-9H-purin-2-amine; 6-(benzyloxy)-7H-purin-2-amine
• IUPAC传统名: 6-(benzyloxy)-9H-purin-2-amine; 6-(benzyloxy)-7H-purin-2-amine
• 别名: 6-(Benzyloxy)-7H-purin-2-amine; 6-(Phenylmethoxy)-9H-purin-2-amine; 2-Amino-6-(benzyloxy)purine; NSC 637037; O6-Benzylguanine; 6-(Benzyloxy)-9H-purin-2-amine; O(6)-Benzylguanine; 6-(Benzyloxy)guanine; 6-O-Benzylguanine; O(6)-bGua; O6-BG; O6-Benzylguanine

登记号

• CAS号: 19916-73-5
• MDL号: MFCD00269931
• PubChem SID: 162035713; 24278259
• PubChem CID: 4578
• Chemspider ID: 4417
• 维基百科标题: O6-Benzylguanine

理论计算性质

• Acid pKa: 10.196849
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 1.6720533
• LogD (pH = 7.4): 1.6714947
• Log P: 1.6721176
• 摩尔折射率: 69.2413 cm^3
• 极化性: 25.45866 Å^3
• 极化表面积: 89.71 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: Aqueous Alkali; methanol: soluble20 mg/mL
• 外观: Light Yellow Solid; solid
• 熔点: >193°C (dec.); 193(dec.)°C
• 密度: 1.432 g/mL

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT; Irritant
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 相关基因信息: human ... MGMT(4255)

产品相关信息

• 纯度: ≥98% (TLC); 95+%

详细说明

Apollo Scientific Ltd - OR7851T

An effective substrate & efficient inactivator of DNA alkyl transferase. Protects against carcinogenic & therapeutic alkylating agents.

Sigma Aldrich - B2292

Biochem/physiol Actions
O(6)-benzylguanine is an antineoplastic agent that binds the DNA repair enzyme O(6)-alkylguanine DNA alkyltransferase (AGT), resulting in inhibition of AGT-mediated DNA repair. It is widely used in various DNA repair mechanism studies and potentiates the effects of other chemotherapeutic agents that damage DNA.

Toronto Research Chemicals - B278500

An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents.

参考文献

• Dolan, M.E., et al.: Proc. Natl. Acad. Sci. USA, 87, 5356 (1990)
• Goodtzova, K., et al.: Biochemistry, 33, 385 (1990)
• Elder, R.H., et al.: Biochem. J., 298, 231 (1994)