2-amino-7-(2-propenyl)-9-<β-D-ribofuranosyl-2',3'-(tetrahydro-4H-pyran-4-one)>purine-6,8(1H)-dione

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-7-(2-propenyl)-9-<β-D-ribofuranosyl-2',3'-(tetrahydro-4H-pyran-4-one)>purine-6,8(1H)-dione
• 英文别名: 9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,4'-oxane]-4-yl]-2-amino-7-prop-2-enyl-1H-purine-6,8-dione
• 化学式: C₁₈H₂₃N₅O₇
• 分子量: 421.41
• InChiKey: DCYCMPDFAUJEBS-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  8-溴鸟苷 在 盐酸 、 sodium hydride 、 原甲酸三乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 2-amino-7-(2-propenyl)-9-<β-D-ribofuranosyl-2',3'-(tetrahydro-4H-pyran-4-one)>purine-6,8(1H)-dione
  参考文献：
  名称：

  Guanosine Derivatives as Immunostimulants. Discovery of Loxoribine

  摘要：

  7-Allyl-8-oxoguanosine (loxoribine, 5) was selected from a series of guanosine derivatives for further evaluation as an immunostimulant. Numerous related analogs were also synthesized and evaluated: 2',3'-ketals of 5 are particularly interesting because they are active, apparently without being cleaved to the free nucleoside.

  DOI：

  10.1080/15257779408013262

文献信息

• Guanosine Derivatives as Immunostimulants. Discovery of Loxoribine
  作者：Robert Chen、Michael G. Goodman、Dennis Argentieri、Stanley C. Bell、Levelle E. Burr、Jon Come、Jacquelyn H. Goodman、Dieter H. Klaubert、Bruce E. Maryanoff、Barbara L. Pope、Marianne S. Rampulla、Mary R. Schott、Allen B. Reitz

  DOI：10.1080/15257779408013262

  日期：1994.3

  7-Allyl-8-oxoguanosine (loxoribine, 5) was selected from a series of guanosine derivatives for further evaluation as an immunostimulant. Numerous related analogs were also synthesized and evaluated: 2',3'-ketals of 5 are particularly interesting because they are active, apparently without being cleaved to the free nucleoside.