6-(1H-pyrrol-1-yl)-1H-purine | 161686-43-7

• 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-(1H-pyrrol-1-yl)-1H-purine
• 英文别名: 6-(pyrrol-1-yl)-9H-purine；6-(pyrrol-1-yl)purine；6-(N-pyrrolyl)purine；6-(N-pyrroyl)purine；6-(1-pyrrolyl)purine；6-pyrrol-1-yl-7H-purine
• CAS: 161686-43-7
• 化学式: C₉H₇N₅
• 分子量: 185.188
• InChiKey: CWBOAMAHXROOMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(1H-pyrrol-1-yl)-1H-purine 在 sodium hydride 、 溶剂黄146 作用下， 反应 1.08h， 生成 (S)-1-(4-Benzhydryl-piperazin-1-yl)-3-(6-pyrrol-1-yl-purin-3-yl)-propan-2-ol
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of 6-Heterocyclic-Substituted Purines as Inactivation Modifiers of Cardiac Sodium Channels

  摘要：

  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.

  DOI：

  10.1021/jm00014a011
• 作为产物：
  描述：

  nor-zeatin 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以10%的产率得到6-(1H-pyrrol-1-yl)-1H-purine
  参考文献：
  名称：

  6-（吡咯-1-基）嘌呤及其某些9-糖苷的合成

  摘要：

  腺嘌呤与2,5-二甲氧基四氢呋喃（3）在甲醇-水的稀乙酸溶液中缓慢反应，得到6-（吡咯-1-基）嘌呤（4）。在更酸性的条件下，4会部分转化为6-（吲哚-1-基）嘌呤（5）和其他未确定的产物。该反应可用于制备的9-糖苷4从设置他们的9糖基键对应的腺嘌呤衍生物是酸水解有所抗性。

  DOI：

  10.1002/jhet.5570310629

文献信息

• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• Synthesis, Structural Studies, and Biological Evaluation of Some Purine Substituted 1-Aminocyclopropane-1-carboxylic Acids and 1-Amino-1-hydroxymethylcyclopropanes
  作者：Zoran Džolić、Vedran Krištafor、Mario Cetina、Ante Nagl、Antonija Hergold-Brundić、Draginja Mrvoš-Sermek、Thomas Burgemeister、Mira Grdiša、Neda Slade、Krešimir Pavelić、Jan Balzarini、Erik De Clercq、Mladen Mintas

  DOI：10.1081/ncn-120022029

  日期：2003.7.1

  purine derivatives of 1-aminocyclopropane-1-carboxylic acid (8 and 9) and 1-amino-1-hydroxymethylcyclopropane (12 and 13) with methylene spacer between the base and the cyclopropane ring were prepared by multistep synthetic route involving alkylation of adenine and 6-(N-pyrrolyl)purine with 2-hydroxymethyl-1-aminocyclopropane-1-carboxylic acid derivative 3 as a key reaction. All novel compounds were

  摘要 通过包括烷基化在内的多步合成路线，制备了碱基与环丙烷环之间带有亚甲基间隔基的 1-氨基环丙烷-1-羧酸（8 和 9）和 1-氨基-1-羟甲基环丙烷（12 和 13）的新型嘌呤衍生物。腺嘌呤和 6-(N-吡咯基)嘌呤与 2-羟甲基-1-氨基环丙烷-1-羧酸衍生物 3 作为关键反应。所有新化合物都是外消旋的。通过分析二维同核和异核中的化学位移、HH 耦合常数和连接性，从它们的 1H 和 13C NMR 谱中推断出 4-13 中嘌呤环的 N-9 取代和环丙烷环的 Z 构型相关谱。通过 X 射线结构分析获得了 1、4 和 5 立体结构的明确证明。在几种细胞系中对新化合物的细胞抑制和抗病毒活性进行了评估。1,2-氨基环丙烷醇 12 的 6-(N-吡咯基) 嘌呤衍生物对宫颈癌 (HeLa) 和人成纤维细胞 (WI-38) 细胞的增殖比其他类型的肿瘤细胞系表现出更显着的抑制活性。这些化合物均未显示
• Nucleoside derivatives for treating hepatitis C virus infection
  申请人：Genelabs Technologies, Inc.

  公开号：US20040147464A1

  公开（公告）日：2004-07-29

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本文揭示了用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  申请人：Roberts Christopher Don

  公开号：US20080249060A1

  公开（公告）日：2008-10-09

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本发明涉及用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• Synthesis and biological evaluation of the novel purine and pyrimidine nucleoside analogues containing 2,3-epoxypropyl, 3-amino-2-hydroxypropyl or 2,3-epoxypropyl ether moieties
  作者：Silvana Raić-Malić、Mira Grdiša、Krešimir Pavelic、Mladen Mintas

  DOI：10.1016/s0223-5234(99)80090-7

  日期：1999.5

  The novel purine and pyrimidine nucleoside analogues possessing a 2,3-epoxypropyl (2a-2c and 8a-8c), 2,3-epoxypropyl ether (3), or 3-amino-2-hydroxypropyl (4a-6c and 9a-9c) moiety bonded at either N-9 of the C-6 substituted purine ring or N-1 and N-3 of the pyrimidine ring, were prepared and evaluated on their antitumour and antiviral activities. Compounds 3, 6b, 8b and sc showed marked inhibition of growth of human tumour cell lines (MiaPaCa(2) and Raji), whilst the inhibitory effect of 6b was greater against Raji cells than to the MiaPaCa2 ones. No specific activity of compounds 2a-3, 4a-6c and 9a-9c against HSV and VZV was detected. The compound 6b was slightly active against the replication of HIV 1 (IIIB), while 2a-2c and 8a-8c were inactive. (C) Elsevier, Paris.