N⁶-benzoyl-9-(2,3-di-O-benzoyl-β-D-xylofuranosyl)adenine | 31079-98-8

• 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: N⁶-benzoyl-9-(2,3-di-O-benzoyl-β-D-xylofuranosyl)adenine
• 英文别名: N6-benzoyl-9-(2',3'-di-O-benzoyl-β-D-xylofuranozyl)-adenine；N,O-Tribenzoyl-6,2',3' β-D-xylofurannosyl-9 adenine；[(2R,3S,4R,5R)-5-(6-benzamidopurin-9-yl)-4-benzoyloxy-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 31079-98-8
• 化学式: C₃₁H₂₅N₅O₇
• 分子量: 579.569
• InChiKey: PDOVRTQXHVPGAF-RUEQBBCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-9-(2,3-di-O-benzoyl-β-D-xylofuranosyl)adenine 在 三正丁胺 、 磷酸三乙酯 、 氨 、 氯磷酸二苯酯 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成
  参考文献：
  名称：

  Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose

  摘要：

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.012
• 作为产物：
  描述：

  N,O-Dibenzoyl-6,3' O-monomethoxytrityl-5' β-D-xylofurannosyl-9 adenine 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 13.5h， 生成 N⁶-benzoyl-9-(2,3-di-O-benzoyl-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  Gosselin, Gilles; Imbach, Jean-Louis, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 597 - 602

  摘要：

  DOI：

文献信息

• Synthesis and biological evaluation of isomeric dinucleoside monophosphates and monomethylphosphonates of 9-.beta.-D-arabinofuranosyladenine and related analogs
  作者：Frederic Puech、Gilles Gosselin、Jan Balzarini、Erik De Clercq、Jean Louis Imbach

  DOI：10.1021/jm00118a006

  日期：1988.10

  The 3'----5',3'----3' and 5'----5' dinucleoside monophosphates and methylphosphonates of 9-beta-D-arabinofuranosyladenine, as well as its 5'-(hydrogen phosphonate) and 5'-(methyl methylphosphonate) derivatives have been the subject of a systematic synthesis and examination of their biological, i.e. antiviral and cytostatic, properties. First the properly protected monomeric building blocks were prepared

  9-β-D-阿拉伯呋喃糖基腺嘌呤及其3'-（磷酸氢根）的3'---- 5'，3'---- 3'和5'---- 5'二核苷单磷酸酯和甲基膦酸酯）和5'-（甲基膦酸甲酯）衍生物一直是系统合成和检查其生物学（即抗病毒和抑制细胞生长）特性的主题。首先制备适当保护的单体结构单元，然后冷凝以得到完全保护的中间体。然后将后者解封，得到未保护的化合物，将其充分表征。仅3'---- 5'磷酸二酯异构体13和16，以及在较小程度上5'-（膦酸氢）衍生物21显示出显着的生物学活性。
• Synthese du trimere de la β--xylofurannosyl-9 adenine a liaisons internucleotidiques 2′→5′.
  作者：G. Gosselin、J.L. Imbach

  DOI：10.1016/s0040-4039(01)83016-1

  日期：1981.1
• PUECH, FREDERIC;GOSSELIN, GILLES;BALZARINI, JAN;DE, CLERCQ ERIK;IMBACH, J+, J. MED. CHEM., 31,(1988) N 10, C. 1897-1907
  作者：PUECH, FREDERIC、GOSSELIN, GILLES、BALZARINI, JAN、DE, CLERCQ ERIK、IMBACH, J+

  DOI：——

  日期：——
• Gosselin, Gilles; Imbach, Jean-Louis, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 597 - 602
  作者：Gosselin, Gilles、Imbach, Jean-Louis

  DOI：——

  日期：——
• Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose
  作者：Christopher J.W Mort、Marie E Migaud、Antony Galione、Barry V.L Potter

  DOI：10.1016/j.bmc.2003.10.012

  日期：2004.1

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.