(2S,3S,4R,5R)-3-Azidomethyl-4-hydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid methylamide | 844665-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R)-3-Azidomethyl-4-hydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid methylamide
• CAS: 844665-70-9
• 化学式: C₁₉H₂₀IN₉O₃
• 分子量: 549.331
• InChiKey: CXQUISCIBPJYHF-OUFKLWKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  162.95
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-3-Azidomethyl-4-hydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid methylamide 在 吡啶 、 三苯基膦 作用下， 反应 1.5h， 以48%的产率得到(2S,3S,4R,5R)-3-Aminomethyl-4-hydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid methylamide
  参考文献：
  名称：

  Exploring human adenosine A3 receptor complementarity and activity for adenosine analogues modified in the ribose and purine moiety

  摘要：

  In this paper we investigated the influence on affinity, selectivity and intrinsic activity upon modification of the adenosine agonist scaffold at the 3- and 5'-positions of the ribofuranosyl moiety and the 2- and N-6-positions of the purine base. This resulted in the synthesis of various analogues, that is, 3-12 and 24-33, with good hA(3)AR selectivity and moderate-to-high affinities (as in 32, K-i = 27 nM). Interesting was the ability to tune the intrinsic activity depending on the substituent introduced at the 3'-position. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.044
• 作为产物：
  描述：

  3-C-azidomethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose 在 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 硫酸 、 氨 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 97.5h， 生成 (2S,3S,4R,5R)-3-Azidomethyl-4-hydroxy-5-[6-(3-iodo-benzylamino)-purin-9-yl]-tetrahydro-furan-2-carboxylic acid methylamide
  参考文献：
  名称：

  Exploring human adenosine A3 receptor complementarity and activity for adenosine analogues modified in the ribose and purine moiety

  摘要：

  In this paper we investigated the influence on affinity, selectivity and intrinsic activity upon modification of the adenosine agonist scaffold at the 3- and 5'-positions of the ribofuranosyl moiety and the 2- and N-6-positions of the purine base. This resulted in the synthesis of various analogues, that is, 3-12 and 24-33, with good hA(3)AR selectivity and moderate-to-high affinities (as in 32, K-i = 27 nM). Interesting was the ability to tune the intrinsic activity depending on the substituent introduced at the 3'-position. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.044