泛昔洛韦杂质7 | 127205-22-5

• 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: 泛昔洛韦杂质7
• 英文名称: 7-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine
• 英文别名: 2-amino-1,7-dihydro-7-(4'-hydroxy-3'-hydroxymethyl)butyl-6-oxo-6H-purine；Famciclovir impurity 7；2-amino-7-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6-one
• CAS: 127205-22-5
• 化学式: C₁₀H₁₅N₅O₃
• 分子量: 253.261
• InChiKey: YVYPCBJWBNCJGP-UHFFFAOYSA-N

物化性质

• 熔点：
  281-283 °C
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  鸟嘌呤 在 palladium on activated charcoal sodium hydroxide 、 甲酸铵 作用下， 以 N-甲基吡咯烷酮 、 甲醇 为溶剂， 反应 39.5h， 生成 泛昔洛韦杂质7
  参考文献：
  名称：

  Regioselective Functionalization of Guanine: Simple and Practical Synthesis of 7- and 9-Alkylated Guanines Starting from Guanosine

  摘要：

  N-2-acetyl-9-和/或-7-苄基化鸟嘌呤8和12与选定的烷基化试剂在120°C的1-甲基-2-吡咯烷酮中反应，得到鸟碱盐9和13。随后，这些盐通过相转移氢化反应，分别以高度选择性的方式转化为N7-和N9-同分异构体10和14。此外，还建立了一种便利的去氧化反应，通过相应的O6-芳烃磺酸酯，将这两种衍生物转化为2-氨基嘌呤的潜在前药。

  DOI：

  10.1055/s-2004-829174

文献信息

• Carba-acyclonucleoside antiherpetic agents
  作者：John Hannah、Richard L. Tolman、John D. Karkas、Richard Liou、Helen C. Perry、A. Kirk Field

  DOI：10.1002/jhet.5570260510

  日期：1989.9

  Ganciclovir 2 and 2′-carba-ganciclovir 5a are anti-viral agents differing structurally only in the replacement of an oxygen by a methylene group and yet expressing their biological properties along mechanistically independent pathways. Methoxy, hydroxy and fluoro derivatives of 2′-carba-ganciclovir were prepared to examine the effect of re-introducing a binding site close to that in the original oxa

  更昔洛韦2和2'-carba-更昔洛韦5a是抗病毒剂，结构上仅在亚甲基取代氧方面有所不同，但仍沿机械独立的途径表达其生物学特性。制备了2'-carba-更昔洛韦的甲氧基，羟基和氟代衍生物，以研究重新引入与原始oxa侧链相近的结合位点的效果。还制备了更昔洛韦的环状磷酸酯。
• HANNAH, JOHN;TOLMAN, RICHARD L.;KARKAS, JOHN D.;LIOU, RICHARD;PERRY, HELE+, J. HETEROCYCL. CHEM., 26,(1989) N, C. 1261-1271
  作者：HANNAH, JOHN、TOLMAN, RICHARD L.、KARKAS, JOHN D.、LIOU, RICHARD、PERRY, HELE+

  DOI：——

  日期：——
• [EN] ANTIVIRAL AGENTS<br/>[FR] AGENTS ANTIVIRAUX
  申请人：COMMW SCIENT IND RES ORG

  公开号：WO2001094348A1

  公开（公告）日：2001-12-13

  This invention relates to a compound of general formula (I) wherein: R1 is hydrogen, halogen, hydroxy, azide, optionally substituted alkoxy, optionally substituted aryloxy, mercapto, optionally substituted thio, optionally substituted amino, optionally substituted hydrazino, or optionally substituted seleno; R2 is hydrogen, halogen, hydroxy, azide, mercapto, optionally substituted thio, or optionally substituted amino; R3 is selected from hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkenyloxy, optionally substituted alkenyloxyalkyl, mercapto, optionally substituted thio, optionally substituted amino, azide, optionally substituted aryloxy, optionally substituted acyl, optionally substituted acyloxy, carboxylic acid, optionally substituted carboxylic ester, optionally substituted carboxylic amide, optionally substituted thioester, optionally substituted sulphonyl, or -O-alkyl-P(O)(OR5)(OR6) or -O-alkyl-P-alkyl-(O)(OR5), wherein R?5 and R6¿ are independently selected from hydrogen, alkyl, ammonium, triethylammonium or an alkali metal or alkaline earth metal ion; R4 together with the oxygen atom to which it is attached forms a hydroxy group, an ester, a carbonate, a carbamate, or a thiocarbonate and salts thereof or -O-alkyl-P(O)(OR5)(OR6) or -O-alkyl-P-alkyl(O)(OR5)(OR6), wherein R?5 and R6¿ are defined above; and n is an integer from 0 to 3, or salts, derivatives, prodrugs, tautomers and/or isomers thereof.
• Regioselective Functionalization of Guanine: Simple and Practical Synthesis of 7- and 9-Alkylated Guanines Starting from Guanosine
  作者：Jože Kobe、Genadiy Kalayanov、Suzana Jakša、Tommaso Scarcia

  DOI：10.1055/s-2004-829174

  日期：——

  Reaction of N 2-acetyl-9- and/or -7-benzylated guanines 8 and 12 with selected alkylating agents in 1-methyl-2-pyrrolidone at 120 °C yielded the guaninium salts 9 and 13. The salts were consequently transformed by phase transfer hydrogenation into N7- and N9-isomers 10 and 14, respectively, in a highly regioselective manner. A convenient deoxygenation of both derivatives, achieved via the corresponding O 6-arenesulfonates, into 2-aminopurine potential prodrugs was also established.

  N-2-acetyl-9-和/或-7-苄基化鸟嘌呤8和12与选定的烷基化试剂在120°C的1-甲基-2-吡咯烷酮中反应，得到鸟碱盐9和13。随后，这些盐通过相转移氢化反应，分别以高度选择性的方式转化为N7-和N9-同分异构体10和14。此外，还建立了一种便利的去氧化反应，通过相应的O6-芳烃磺酸酯，将这两种衍生物转化为2-氨基嘌呤的潜在前药。