9-[(R)-3-[(2S,3R,4R,5R)-3-Benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine | 418766-90-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 9-[(R)-3-[(2S,3R,4R,5R)-3-Benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine
• CAS: 418766-90-2
• 化学式: C₄₄H₄₆N₅O₁₅P₃
• 分子量: 977.795
• InChiKey: WIBFJEXVMYXXIV-JPYIPXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  67.0
• 可旋转键数：
  14.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  231.59
• 氢给体数：
  1.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  9-[(R)-3-[(2S,3R,4R,5R)-3-Benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以98%的产率得到[(2R)-3-(6-amino-9H-purin-9-yl)-2-(phosphonooxy)propyl] α-D-xylopyranoside 3,4-bisphosphate hexasodium salt
  参考文献：
  名称：

  d-myo-Inositol-1,4,5-trisphosphate and Adenophostin Mimics: Importance of the Spatial Orientation of a Phosphate Group on the Biological Activity

  摘要：

  Three different routes for the synthesis of heterocyclic analogues of the second messenger D-myo-inositol-1,4,5-trisphosphate (InsP(3)) and the natural adenophostins. starting from allyl D-xyloside are described. The two diastereoisomers at C-2 of new compounds. which we named xylophostins, were obtained. The preliminary biological studies shows that the presence of the adenine residue has a beneficial effect on the affinity for the receptor. The low potency of one of the two diastereoisomeric compounds shows that the configuration of the carbon bearing the non-vicinal phosphate group is an important requirement for a high affinity to the receptor. These results provide evidence for the existence of a binding pocket for the adenine ring nearby the InsP(3) binding site. The consequence of these stabilizing interactions should be to place the phosphate group in a suitable position to perfectly mimic InsP(3) in the more active diastereoisomer. Obviously, in the other diastereoisomer, the phosphate cannot accommodate the same orientation, thus explaining the low affinity. The existence of such a binding pocket for adenine is in line with the high potency of adenophostins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00329-7
• 作为产物：
  描述：

  allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside 在 四氮唑 、 sodium hydride 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.92h， 生成 9-[(R)-3-[(2S,3R,4R,5R)-3-Benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine
  参考文献：
  名称：

  d-myo-Inositol-1,4,5-trisphosphate and Adenophostin Mimics: Importance of the Spatial Orientation of a Phosphate Group on the Biological Activity

  摘要：

  Three different routes for the synthesis of heterocyclic analogues of the second messenger D-myo-inositol-1,4,5-trisphosphate (InsP(3)) and the natural adenophostins. starting from allyl D-xyloside are described. The two diastereoisomers at C-2 of new compounds. which we named xylophostins, were obtained. The preliminary biological studies shows that the presence of the adenine residue has a beneficial effect on the affinity for the receptor. The low potency of one of the two diastereoisomeric compounds shows that the configuration of the carbon bearing the non-vicinal phosphate group is an important requirement for a high affinity to the receptor. These results provide evidence for the existence of a binding pocket for the adenine ring nearby the InsP(3) binding site. The consequence of these stabilizing interactions should be to place the phosphate group in a suitable position to perfectly mimic InsP(3) in the more active diastereoisomer. Obviously, in the other diastereoisomer, the phosphate cannot accommodate the same orientation, thus explaining the low affinity. The existence of such a binding pocket for adenine is in line with the high potency of adenophostins. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00329-7