9-ethyl-8-hydroxyguanine | 21823-85-8

• 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: 9-ethyl-8-hydroxyguanine
• 英文别名: 9-Ethyl-8-hydroxyguanine；2-amino-9-ethyl-1,7-dihydropurine-6,8-dione
• CAS: 21823-85-8
• 化学式: C₇H₉N₅O₂
• 分子量: 195.181
• InChiKey: RDCYUHHDQOSVQP-UHFFFAOYSA-N

物化性质

• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-乙基鸟嘌呤 在 phosphate buffer 、 乙二胺四乙酸 、 氧气 、 iron(II) sulfate 、 维生素 C 作用下， 以15%的产率得到9-ethyl-8-hydroxyguanine
  参考文献：
  名称：

  The Crystal Structure of 9-Ethyl-8-hydroxyguanine

  摘要：

  利用 X 射线衍射分析 9-乙基-8-羟基鸟嘌呤的晶体结构表明，它是 C-8 酮形式。与 9-乙基鸟嘌呤相比，咪唑环的键长和键角有显著差异。

  DOI：

  10.1246/bcsj.60.3799

文献信息

• The Crystal Structure of 9-Ethyl-8-hydroxyguanine
  作者：Hiroshi Kasai、Susumu Nishimura、Yoshiharu Toriumi、Akiko Itai、Yoichi Iitaka

  DOI：10.1246/bcsj.60.3799

  日期：1987.10

  Analysis of the crystal structure of 9-ethyl-8-hydroxyguanine using X-ray diffraction showed that it is in C-8 keto form. As compared with 9-ethylguanine, significant differences were observed in bond lengths and bond angles of the imidazole ring.

  利用 X 射线衍射分析 9-乙基-8-羟基鸟嘌呤的晶体结构表明，它是 C-8 酮形式。与 9-乙基鸟嘌呤相比，咪唑环的键长和键角有显著差异。
• Polymer
  申请人：CANON KABUSHIKI KAISHA

  公开号：US10808059B2

  公开（公告）日：2020-10-20

  To determine and detect 8-oxo-2′-deoxyguanosine in an aqueous sample solution with high sensitivity and specifically, provided is a polymer including a repetition structure represented by any one of the following general formulae 2 to 5, in which a group represented by any one of the following general formulae 6 to 11 is linked to the repetition structure represented by any one of the following general formulae 2 to 5 through a divalent linking group L.

  为了高灵敏度地测定和检测水样溶液中的 8-氧代-2′-脱氧鸟苷，特别提供了一种聚合物，该聚合物包括以下通式 2 至 5 中任一项所代表的重复结构，其中以下通式 6 至 11 中任一项所代表的基团通过二价连接基团 L 与以下通式 2 至 5 中任一项所代表的重复结构相连。
• The discovery of purine-based agents targeting triple-negative breast cancer and the αB-crystallin/VEGF protein–protein interaction
  作者：Nelly A. Fosu-Mensah、Wen Jiang、Andrea Brancale、Jun Cai、Andrew D. Westwell

  DOI：10.1007/s00044-018-2275-9

  日期：2019.2

  Oestrogen receptor-negative breast cancer, particularly subtypes such as triple-negative breast cancer (TNBC, around 10-15% of cases), are characterised by poor long-term survival, poor response to therapy and early progression to metastasis. Purine-based compounds represent a privileged scaffold in anticancer drug design, with several clinically approved and experimental agents in clinical development comprising a purine core structure. In this study, a series of new purine-based compounds were synthesised; seven of the new analogues were found to significantly reduce the in vitro viability of TNBC cell lines (MDA-MB-231 and MDA-MB-436) with IC50 values of 50M. In previous work, we have proposed a new concept for targeting angiogenesis driving TNBC progression, by disrupting the protein-protein interaction between the molecular chaperone B-crystallin (CRYAB) and VEGF. Since previous clinical studies applying anti-VEGF therapy to TNBC patients have met with limited success, we were interested to test our most promising purine analogues against CRYAB/VEGF, using a custom-designed cell-based CRYAB/VEGF(165) interaction assay platform. Analogues 4e and 4f significantly reduced the interaction between CRYAB/VEGF(165), and compound 4e (100M) was also found to decrease the levels of soluble VEGF expressed by MDA-MB-231 cells by 40%. In conclusion, these promising early activity profiles warrant further investigation to validate this concept.
• Electrophilic amination of imidazole moieties of 9-ethylguanine and 1-methylbenzimidazole derivatives and reactivities of N-aminated products
  作者：Toyo Kaiya、Masahiro Ohta、Kohfuku Kohda

  DOI：10.1016/s0040-4020(01)81901-3

  日期：——

  Electrophilic amination of four 9-ethylguanine derivatives and seven 1-methylbenzimidazole derivatives with 2,4-dinitrophenoxyamine was carried out. N-amination proceeded at the imidazole moiety of these compounds with pKa's of more than 3.2. Treatment of these N-aminated derivatives with 0.1 N NaOH gave different results depending on their structures. Reactivity of the imidazole moiety to electrophilic amination and the reaction pathways of N-aminated compounds with alkaline treatment are discussed.