8-Hydroxyacyclovir | 80685-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-Hydroxyacyclovir
• 英文别名: 2-amino-9-[(2-hydroxyethoxy)methyl]-7,9-dihydro-1H-purine-6,8-dione；8-hydroxy-9-(2-hydroxyethoxymethyl)guanine；2-amino-9-(2-hydroxyethoxymethyl)-1,7-dihydropurine-6,8-dione
• CAS: 80685-23-0
• 化学式: C₈H₁₁N₅O₄
• 分子量: 241.206
• InChiKey: PTSDSAPWOJZBNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  阿昔洛韦 在 溴 、 sodium acetate 、 C.I.酸性橙108 作用下， 以 水 为溶剂， 反应 11.5h， 生成 8-Hydroxyacyclovir
  参考文献：
  名称：

  阿昔洛韦代谢物 8-羟基阿昔洛韦和 9-(羧甲氧基甲基)鸟嘌呤的实用合成

  摘要：

  研究了合成阿昔洛韦代谢物 8-羟基阿昔洛韦和 9-(羧甲氧基甲基)鸟嘌呤的改进方法。发现该方法可用于高纯度的8-羟基阿昔洛韦和9-(羧甲氧基甲基)鸟嘌呤的实际制备。对 DMSO-d 6 中 8-羟基阿昔洛韦的仔细光谱分析表明，在溶液条件下，它可能以 8-氧代互变异构体而不是 8-羟基互变异构体的形式存在。

  DOI：

  10.3987/com-05-10430

文献信息

• Nucleic acid related compounds. 47. Synthesis and biological activities of pyrimidine and purine "acyclic" nucleoside analogs
  作者：Morris J. Robins、Peter W. Hatfield、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00377a018

  日期：1984.11

  Various acyclic, i.e., (2-hydroxyethoxy)methyl and (2-acetoxyethoxy)methyl, analogues of pyrimidine and purine nucleosides have been prepared and evaluated for their antiviral, antimetabolic, and cytotoxic properties. All of the pyrimidine analogues, including (E)-5-(2-bromovinyl)-1-[(2-hydroxyethoxy)methyl]uracil (12) and its O-acetyl derivative (13), were virtually devoid of antiviral, cytotoxic

  已经制备了嘧啶和嘌呤核苷的各种无环的，即（2-羟基乙氧基）甲基和（2-乙酰氧基乙氧基）甲基类似物，并评估了它们的抗病毒，抗代谢和细胞毒性特性。所有嘧啶类似物，包括（E）-5-（2-溴乙烯基）-1-[（2-羟基乙氧基）甲基]尿嘧啶（12）及其O-乙酰基衍生物（13），都几乎没有抗病毒，细胞毒性以及抗代谢活动。但是，几种9-[（（2-羟基乙氧基）甲基]鸟嘌呤（acyclovir）的8取代衍生物在体外具有比母体药物更高的抗病毒特异性。8-甲基-，8-氨基-，8-溴-和8-碘代阿昔洛韦衍生物具有值得进一步研究的活性。
• Adsorptive Square Wave Voltammetric Determination of Acyclovir and Its Application in a Pharmacokinetic Study Using a Novel Sensor of β-Cyclodextrin Modified Pencil Graphite Electrode
  作者：Gamal A. Saleh、Hassan F. Askal、Ibrahim H. Refaat、Fatma A. M. Abdel-aal

  DOI：10.1246/bcsj.20150112

  日期：2015.9.15

  An electrochemical sensor for acyclovir (ACV) based on polymerization of β-cyclodextrin (β-CD) on electrochemically pretreated pencil graphite electrode (PGE) was built for the first time. A synergistic effect of β-CD was used to construct this sensor for quantification of this important drug. Scanning electron microscope (SEM) images show that polymer of β-CD has been successfully modified on the electrode. Square wave voltammetry (SWV) exhibited two linear dynamic ranges of 5 × 10−8 to 6 × 10−7 M and 1 × 10−6 to 9 × 10−6 M of ACV for its oxidation and the detection limit was found to be as low as 7.59 × 10−9 M of ACV. The parameters affecting ACV oxidation were investigated. The prepared electrodes showed good fabrication reproducibility. The analytical applications of the prepared electrodes were tested by using ACV dosage forms and human urine as a real sample. The SWV analysis has been successfully applied to pharmacokinetic studies of ACV in health human volunteers after oral administration of a single dose of Zovirax suspension (400 mg/5 mL).
• A Practical Synthesis of 8-Hydroxyacyclovir and 9-(Carboxymethoxymethyl)guanine, Metabolites of Acyclovir
  作者：Tsutomu Yokomatsu、Teruo Kutsuma、Yasuo Sakai、Hiroyuki Ouchi、Noriaki Shiina、Takehiro Yamagishi、Shiroshi Shibuya

  DOI：10.3987/com-05-10430

  日期：——

  Improved methods for the synthesis of 8-hydroxyacyclovir and 9-(carboxymethoxymethyl)guanine, metabolites of acyclovir, were examined. The methods were found to be useful for practical preparation of 8-hydoxyacyclovir and9-(caboxymethoxymethyl)guanine of high purity. Careful spectroscopic analysis of 8-hydroxyacyclovir in DMSO-d 6 suggested that it may be exist in an 8-oxo tautomer rather than an 8-hydroxy

  研究了合成阿昔洛韦代谢物 8-羟基阿昔洛韦和 9-(羧甲氧基甲基)鸟嘌呤的改进方法。发现该方法可用于高纯度的8-羟基阿昔洛韦和9-(羧甲氧基甲基)鸟嘌呤的实际制备。对 DMSO-d 6 中 8-羟基阿昔洛韦的仔细光谱分析表明，在溶液条件下，它可能以 8-氧代互变异构体而不是 8-羟基互变异构体的形式存在。