2-氨基-9-(2-羟基乙氧基甲基)-1-甲基嘌呤-6-酮 | 82145-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-氨基-9-(2-羟基乙氧基甲基)-1-甲基嘌呤-6-酮
• 英文名称: 9-[(2-hydroxyethoxy)methyl]-1-methylguanine
• 英文别名: 9-(2-Hydroxyethoxymethyl)-1-methylguanine；1-methylacyclovir；1-Methyl-9-(2-hydroxyethoxymethyl)guanine；2-amino-9-(2-hydroxyethoxymethyl)-1-methylpurin-6-one
• CAS: 82145-52-6
• 化学式: C₉H₁₃N₅O₃
• 分子量: 239.234
• InChiKey: YUYWPANFAWBVET-UHFFFAOYSA-N

物化性质

• 熔点：
  253 °C
• 沸点：
  567.0±58.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-9-(2-羟基乙氧基甲基)-1-甲基嘌呤-6-酮 生成 2-Amino-9-(2-hydroxyethoxymethyl)-1,7-dimethylpurin-9-ium-6-one;iodide
  参考文献：
  名称：

  MACCOSS, M.;TOLMAN, R. L.;STRELITZ, R. A.

  摘要：

  DOI：
• 作为产物：
  描述：

  9-(2-Benzoxyethoxymethyl)-1-methylguanine 在 sodium 作用下， 以 氨 为溶剂， 以73%的产率得到2-氨基-9-(2-羟基乙氧基甲基)-1-甲基嘌呤-6-酮
  参考文献：
  名称：

  嘌呤和咪唑核苷的无环类似物

  摘要：

  的1-和3-（2-羟基乙氧基甲基）咪唑（羟基被保护的衍生物4,5,7-10）已经从5-氨基-4- carbamoylimidazoles（制备2）。将受保护的衍生物转化为咪唑核苷的无环类似物（6）或进行各种环化反应，生成9-（2-羟基-乙氧基甲基）取代的2-甲基-，2-苯基-和2-氮杂泛黄嘌呤（18,13和分别为20和1-甲基鸟嘌呤（28）。为了将结构分配给异构的咪唑和嘌呤衍生物，已使用13 C化学位移。

  DOI：

  10.1002/jhet.5570190104

文献信息

• N-alkylguanine acyclonucleosides as antiviral agents
  申请人：Merck & Co., Inc.

  公开号：US04579849A1

  公开（公告）日：1986-04-01

  Disclosed are compounds of the formula: ##STR1## and the pharmaceutically acceptable salts thereof wherein R.sup.1 and R.sup.2 are independently alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl, each having 1 to 19 carbon atoms, or R.sup.2 is hydrogen; R.sup.3 is hydrogen, alkyl having 1 to 6 carbon atoms or hydroxyalkyl having 1 to 6 carbon atoms; R.sup.4 is hydrogen, halogen, amino or alkyl having 1 to 4 carbon atoms; R.sup.5, R.sup.6 and R.sup.7 are independently selected from hydrogen, hydroxy, alkyl having 1 to 6 carbon atoms, acyloxy having 1 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, hydroxyalkyl having 1 to 6 carbon atoms, acyloxyalkyl having 1 to 12 carbon atoms, amino, alkylamino of 1 to 6 carbon atoms and --PO.sub.3.sup.=, or two of R.sup.5, R.sup.6 and R.sup.7 taken together form a group --OPO.sub.2 O.sup.- --, --CH.sub.2 OPO.sub.2 O.sup.- --, --CH.sub.2 OPO.sub.2 OPO.sub.2 O.sup.= --, or --OPO.sub.2 OPO.sub.2 O.sup.= --; A is O, S or CH.sub.2 and X is a pharmaceutically acceptable anion. The compounds have antiviral activity, especially against viruses of the herpes class.

  本发明涉及以下公式的化合物：##STR1##及其药学上可接受的盐，其中R.sup.1和R.sup.2分别是独立的烷基，卤代烷基，烯基，卤代烯基，炔基或卤代炔基，每个具有1至19个碳原子，或R.sup.2是氢; R.sup.3是氢，具有1至6个碳原子的烷基或具有1至6个碳原子的羟基烷基; R.sup.4是氢，卤素，氨基或具有1至4个碳原子的烷基; R.sup.5，R.sup.6和R.sup.7分别选自氢，羟基，具有1至6个碳原子的烷基，具有1至8个碳原子的酰氧基，具有1至6个碳原子的烷氧基，具有1至6个碳原子的羟基烷基，具有1至12个碳原子的酰氧基烷基，氨基，具有1至6个碳原子的烷基氨基和--PO.sub.3.sup.=，或R.sup.5，R.sup.6和R.sup.7中的两个结合形成一个--OPO.sub.2 O.sup.- --，--CH.sub.2 OPO.sub.2 O.sup.- --，--CH.sub.2 OPO.sub.2 OPO.sub.2 O.sup.= --，或--OPO.sub.2 OPO.sub.2 O.sup.= --的基团; A为O，S或CH.sub.2，X为药学上可接受的阴离子。该化合物具有抗病毒活性，特别是对于疱疹病毒类的病毒。
• Synthesis and antiviral activity of novel N-substituted derivatives of acyclovir
  作者：Jerzy Boryski、Bozenna Golankiewicz、Erik De Clercq

  DOI：10.1021/jm00402a017

  日期：1988.7

  Novel N-substituted derivatives of acyclovir (1a) were synthesized and evaluated for their antiviral, antimetabolic, and antitumor cell properties in vitro. Monomethylation of 1a at positions 1, 7, and N-2 gave compounds 2-4, respectively. When positions 1 and N-2 were linked together by an isopropeno group, the tricyclic 9-[(2-hydroxyethoxy)methyl]-1,N-2-isopropenoguanine (5) was obtained. Compound 5 was then further methylated at positions N-2 and 7 to give 6 and 7, respectively. None of the new acyclovir derivatives showed any appreciable antimetabolic or antitumor cell activity. However, compounds 2 and 5 exhibited a marked antiherpetic activity. Their activity spectrum was similar to that of acyclovir, and their selectivity as inhibitors of herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) was at least as great as, if not greater than, that of acyclovir.
• BORYSKI, JERZY;GOLANKIEWICZ, BOZENNA;DE, CLERCQ ERIK
  作者：BORYSKI, JERZY、GOLANKIEWICZ, BOZENNA、DE, CLERCQ ERIK

  DOI：——

  日期：——
• BORYSKI, JERZY;GOLANKIEWICZ, BOZENNA;DE, CLERCQ ERIK, J. MED. CHEM., 31,(1988) N 7, C. 1351-1355
  作者：BORYSKI, JERZY、GOLANKIEWICZ, BOZENNA、DE, CLERCQ ERIK

  DOI：——

  日期：——
• BIOORTHOGONAL METHODS AND COMPOUNDS
  申请人：THE UNIVERSITY COURT OF THE UNIVERSITY OF EDINBURGH

  公开号：US20160152573A1

  公开（公告）日：2016-06-02

  The invention provides a new bioorthogonal deprotection method for preparing heterocyclic compounds by bond cleavage using palladium. The methods have general application in the field of biological synthetic chemistry. Compounds, such as prodrugs, which are useful in such methods are also provided.