6-(phenylethynyl)-9H-purine | 85110-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-(phenylethynyl)-9H-purine
• 英文别名: 6-phenylethynylpurine；6-(2-phenylethynyl)-9H-purine；6-(2-phenylethynyl)-7H-purine
• CAS: 85110-23-2
• 化学式: C₁₃H₈N₄
• 分子量: 220.233
• InChiKey: NKUNFDKMCBTYIH-UHFFFAOYSA-N

物化性质

• 沸点：
  348.2±52.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(phenylethynyl)-9H-purine 在 氢溴酸 作用下， 以 甲醇 为溶剂， 生成 (E)-6-(2-bromo-2-phenylethenyl)purine
  参考文献：
  名称：

  Synthesis, crystal structure and cytokinin activities of β-substituted 6-styrylpurines

  摘要：

  Conformationally restricted (Z)- and (E)-beta-substituted 6-styrylpurines were synthesized by addition reaction to 6-phenylethynylpurine and photoisomerization. The crystalline (Z)- and (E)-beta-chloro-substituted compounds exist in the anti- and syn-forms, respectively. While the (Z)-beta-chloro- and bromo-substituted compounds were almost as active as (E)-6-styrylpurine and N-6-benzyladenine (BA) in the Amaranthus betacyanin assay, they were more active than the latter in the tobacco callus assay. On the other hand, their (E)-isomers showed activities almost comparable to that of kinetin in both assays. The crystal structure, as well as the high cytokinin activity of the conformationally restricted (Z)-isomers strongly suggest that the anti-transoid form is most probably the active conformation of purine cytokinins.

  DOI：

  10.1016/s0031-9422(00)89504-7
• 作为产物：
  描述：

  6-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成 6-(phenylethynyl)-9H-purine
  参考文献：
  名称：

  Antioxidant activity of synthetic cytokinin analogues: 6-alkynyl- and 6-alkenylpurines as novel 15-Lipoxygenase inhibitors

  摘要：

  Synthetic cytokinin analogues as well as the well known CKs 6-benzylaminopurine (BAP), kinetin and trans-zeatin were examined for antioxidant activity. The compounds were tested as potential diphenylpicrylhydrazyl (DPPH) scavengers and as inhibitors of 15-lipoxygenase (15-LO). The natural plant hormones were essentially inactive in both assays, but several synthetic analogues have a profound inhibiting effect on 15-lipoxygenase from soybeans. The same compounds were only weak DPPH scavengers and they may therefore be regarded as so-called non antioxidant inhibitors of 15-LO. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00427-8

文献信息

• Synthesis and Structure-Activity Relationships of 6-Heterocyclic-Substituted Purines as Inactivation Modifiers of Cardiac Sodium Channels
  作者：Kimberly G. Estep、Kurt A. Josef、Edward R. Bacon、Philip M. Carabateas、Squire Rumney、Garry M. Pilling、Douglas S. Krafte、Walter A. Volberg、Kathleen Dillon、Nancy Dugrenier、G. Maurice Briggs、Paul C. Canniff、William P. Gorczyca、Gerald P. Stankus、Alan M. Ezrin

  DOI：10.1021/jm00014a011

  日期：1995.7

  Purine-based analogs of SDZ 211-500 (5) were prepared and evaluated as inactivation modifiers of guinea pig or human cardiac sodium (Na) channels expressed in Xenopus oocytes. Substances which remove or slow the Na channel inactivation process in cardiac tissue are anticipated to prolong the effective refractory period and increase inotropy and thus have potential utility as antiarrhythmic agents. Heterocyclic substitution at the 6-position of the purine ring resulted in compounds with increased Na activity and potency, with 5-membered heterocycles being optimal. Only minor modifications to the benzhydrylpiperazine side chain were tolerated. Selected compounds which delayed the inactivation of Na channels were found to increase refractoriness and contractility in a rabbit Langendorff heart model, consistent with the cellular mechanism. Activity in both the oocyte and rabbit heart assays was specific to the S enantiomers. Preliminary in vivo activity has been demonstrated following intravenous infusion. The most promising compound on the basis of in vitro data is the formylpyrrole (S)-74, which is 25-fold more potent than DPI 201-106 (1) in the human heart Na channel assay.
• Suzuki−Miyaura and Sonogashira Coupling of 6-Chloropurines and -Nucleosides in Water
  作者：Jan Pschierer、Herbert Plenio

  DOI：10.1021/ol9007475

  日期：2009.6.18

  A general protocol is reported for the efficient Suzuki-Miyaura and the copper-free Sonogashira coupling of unprotected 6-chloropurines and unprotected beta-D-ribofuranosyl-6-chloropurine in water or in water/n-butanol utilizing Na2PdCl4 and a disulfonated and highly water-soluble fluorenylphosphine (cataCXium F sulk).
• Nishikawa, Shiro; Kumazawa, Zenzaburo; Mizutani, Hiroyuki, Agricultural and Biological Chemistry, 1986, vol. 50, # 4, p. 1089 - 1092
  作者：Nishikawa, Shiro、Kumazawa, Zenzaburo、Mizutani, Hiroyuki、Kashimura, Naoki

  DOI：——

  日期：——
• Nishikawa, Shiro; Kumazawa, Zenzaburo; Kashimura, Naoki, Agricultural and Biological Chemistry, 1985, vol. 49, # 11, p. 3353 - 3354
  作者：Nishikawa, Shiro、Kumazawa, Zenzaburo、Kashimura, Naoki、Mizutani, Hiroyuki、Kondo, Hiromi

  DOI：——

  日期：——
• Synthesis, crystal structure and cytokinin activities of β-substituted 6-styrylpurines
  作者：Shiro Nishikawa、Fumio Yamashita、Naoki Kashimura、Zenzaburo Kumazawa、Naoko Oogami、Hiroshi Mizuno

  DOI：10.1016/s0031-9422(00)89504-7

  日期：1994.11

  Conformationally restricted (Z)- and (E)-beta-substituted 6-styrylpurines were synthesized by addition reaction to 6-phenylethynylpurine and photoisomerization. The crystalline (Z)- and (E)-beta-chloro-substituted compounds exist in the anti- and syn-forms, respectively. While the (Z)-beta-chloro- and bromo-substituted compounds were almost as active as (E)-6-styrylpurine and N-6-benzyladenine (BA) in the Amaranthus betacyanin assay, they were more active than the latter in the tobacco callus assay. On the other hand, their (E)-isomers showed activities almost comparable to that of kinetin in both assays. The crystal structure, as well as the high cytokinin activity of the conformationally restricted (Z)-isomers strongly suggest that the anti-transoid form is most probably the active conformation of purine cytokinins.