2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine | 24880-52-2

• 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: 2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine
• 英文别名: 2-amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-adenine；9-(tri-O-benzyl-β-D-arabinofuranosyl)-9H-purine-2,6-diamine；2-amino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)adenine；2-amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl) adenine；2-Amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine；9-[(2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]purine-2,6-diamine
• CAS: 24880-52-2
• 化学式: C₃₁H₃₂N₆O₄
• 分子量: 552.633
• InChiKey: OLAYGHLOZNVHSE-JVYBIVSJSA-N

物化性质

• 沸点：
  801.3±75.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine 在 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 生成 2-fluoro-9-(2,3,5-tri-o-benzyl-beta-D-arabinofuranosyl)adenine
  参考文献：
  名称：

  Anticancer and antiviral activity of

  摘要：

  利用9-β-D-阿拉伯呋喃糖基-2-氟腺嘌呤，即2-F-AraA（NSC 118218），用于治疗小鼠白血病，并作为DNA病毒的抗病毒剂，如DNA病毒单纯疱疹病毒I型和培养在H.Ep-2细胞中的天花病毒。2-F-AraA的可操作用量为1-10天的治疗时间，每天2-8次，每次8-400毫克/千克。进一步发现，在一个为期10天的治疗计划中，第1、5和第9天的单剂量给出了令人满意的结果。

  公开号：

  US04188378A1
• 作为产物：
  描述：

  2,6-Di(methoxyacetamido)-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2,6-diamino-9-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)purine
  参考文献：
  名称：

  Hydrogenation of

  摘要：

  描述了一种通过氯化钯和盐酸与2-氟-9-(2,3,5-三苄基-β-D-阿拉伯呋喃核糖基)腺嘌呤(VI)在溶剂中在升高的压力下反应制备2-氟-9-β-D-阿拉伯呋喃核糖基嘌呤(VII)的方法。该反应快速、经济高效。

  公开号：

  US05296589A1

文献信息

• Process for the preparation of
  申请人：Ash Stevens, Inc.

  公开号：US05110919A1

  公开（公告）日：1992-05-05

  A process for the preparation of 2,6-diamino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)purine (V) by reacting 2,6-di(alkoxyacetamido)purine (II) with 2,3,5-tri-O-benzyl-1-chloro-alpha-D-arabinofuranose (III) to produce 2,6-di(alkoxyacetamido)-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)puri ne (IV) and then deprotecting the 2,6-positions to produce the 2,6-diamine (V) is described. The process provides purine (V) in high yield. Purine (V) is an intermediate in the preparation of 9-beta-D-arabinofuranosyl-2-fluoroadenine which is a cytotoxic agent.

  通过将2,6-二（烷氧基乙酰胺基）嘌呤（II）与2,3,5-三-O-苄基-1-氯-α-D-阿拉伯呋喃糖（III）反应，制备2,6-二（烷氧基乙酰胺基）-9-(2,3,5-三-O-苄基-β-D-阿拉伯呋喃糖基)嘌呤（IV），然后去保护2,6-位置以产生2,6-二胺（V）的方法被描述。该过程提供高产率的嘌呤（V）。嘌呤（V）是制备细胞毒药物9-β-D-阿拉伯呋喃基-2-氟腺嘌呤的中间体。
• Purine sugar derivatives
  申请人：Burroughs Wellcome Co.

  公开号：US03956277A1

  公开（公告）日：1976-05-11

  This invention relates to purine sugar derivatives which are useful as suppressors of the immune response and as antiviral agents, and to methods of preparation thereof.

  本发明涉及嘌呤糖衍生物，其可用作抑制免疫反应和抗病毒剂，并涉及其制备方法。
• Procedure for the preparation of
  申请人：The United States of America as represented by the Department of Health,

  公开号：US04210745A1

  公开（公告）日：1980-07-01

  The present invention is an improved multi-step process for the production of 9-.beta.-D-arabinofuranosyl-2-fluoroadenine (2-F-AraA) and an improvement over the process of Montgomery and Hewson, J. Med. Chem., 12:498 (1969). This compound is an important tool in antitumor therapy and has shown activity against leukemia L1210 and P388 in animals as well as being a potent antiviral agent. Its therapeutic effectiveness occurs because 2-F-AraA is not a substrate for adenosine deaminase which vitiated against the activity of the parent compound 9-.beta.-D-arabinofuranosyladenine (araA) as indicated in experimental animal cancers. An advantage of making 2-F-AraA by the present process is that there is a sharply increased yield based on the chlorosugar up to about 400 percent. In the present improved process the differences lie in utilizing as a reactant 2,4,5,6-tetraaminopyrimidine; the acetylation of 2-aminoadenine in acetic acid and pyridine; the reaction of 2,6-diacetamidopurine with chlorosugar in ethylene chloride in the presence of a molecular sieve and subsequent deacetylation with methanolic sodium methoxide. Further, the diazotization step is carried out in a homogenous mixture of tetrahydrofuran and fluoboric acids. Finally, the O-benzyl groups are removed by the use of boron trichloride in ether.

  本发明是一种改进的多步骤生产9-β-D-阿拉伯核糖基-2-氟腺嘌呤（2-F-AraA）的过程，并对Montgomery和Hewson的过程（J. Med. Chem.，12：498（1969））进行了改进。该化合物是抗肿瘤治疗的重要工具，已在动物的白血病L1210和P388中显示出活性，同时也是一种有效的抗病毒剂。其治疗效果是因为2-F-AraA不是腺苷脱氨酶的底物，这削弱了父化合物9-β-D-阿拉伯核糖基腺嘌呤（araA）在实验动物癌症中的活性。使用本发明的方法制备2-F-AraA的一个优点是，基于氯代糖，产量显著增加了约400％。在本改进的过程中，差异在于将2,4,5,6-四氨基嘧啶作为反应物；在乙酸和吡啶中乙酰化2-氨基腺嘌呤；在存在分子筛的氯乙烷中，2,6-二乙酰基嘌呤与氯代糖反应，随后使用甲醇钠甲醇酸盐进行脱乙酰化。此外，重氮化步骤在四氢呋喃和氟硼酸的均相混合物中进行。最后，使用三氯化硼在醚中去除O-苄基基团。
• An Efficient and Scalable Synthesis of Arabinosylguanine and 2′-Deoxy-2′-Fluoro-guanosine
  作者：Bruce S. Ross、Robert H. Springer、Kelly G. Sprankle、Guillermo Vasquez

  DOI：10.1080/07328319708006246

  日期：1997.7

  An efficient conversion from commercially available 2,6-diaminopurine-2',3',5'-tri-O-benzyl arabinoside to arabinosylguanine and its further transformation to 2'-deoxy-2'-fluoro-guanosine is outlined. This process has been used to produce more than one hundred grams of final product.
• Improved process for the preparation of 2-amino(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine
  申请人：ASH STEVENS, INC.

  公开号：EP0461407B1

  公开（公告）日：1997-07-30