2-(4-溴苯胺基)-3,7-二氢嘌呤-6-酮 | 123994-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-(4-溴苯胺基)-3,7-二氢嘌呤-6-酮
• 英文名称: p-BrPG
• 英文别名: N²-(p-bromophenyl)guanine；6H-Purin-6-one, 2-((4-bromophenyl)amino)-1,9-dihydro-；2-(4-bromoanilino)-1,7-dihydropurin-6-one
• CAS: 123994-72-9
• 化学式: C₁₁H₈BrN₅O
• 分子量: 306.121
• InChiKey: LAAOZGLNGLIEGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 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：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-溴苯胺基)-3,7-二氢嘌呤-6-酮 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 N2-(p-bromophenyl)-9-β-D-ribofuranosylguanine
  参考文献：
  名称：

  Interaction of GTP derivatives with cellular and oncogenic ras-p21 proteins

  摘要：

  A series of N2-substituted guanosine 5'-triphosphates was synthesized from the corresponding nucleosides. The nucleosides were prepared by treatment of N2-substituted guanines with tetra-O-acetylribose under conditions which maximized the yield of the 9-beta-guanosine isomers. These nucleotides and several sugar- and base-modified analogues of GTP were tested for their ability to bind to cellular and oncogenic forms of the GTP/GDP binding proteins, Ha-ras-p21. Several N2-substituted GTPs showed affinities higher than that of GDP itself, and the N2-[p-(n-butyl)phenyl] derivative bound to the oncogenic mutant, Leu-61 p21, twice as strongly as to the cellular protein. Changes in relative affinities of the nucleotides are discussed with reference to reported crystallographic structures of p21.

  DOI：

  10.1021/jm00108a010
• 作为产物：
  描述：

  2-溴次黄嘌呤 以61%的产率得到
  参考文献：
  名称：

  NOONAN, TIMOTHY;BROWN, NEAL;DUDYCZ, LECH;WRIGHT, GEORGE, J. MED. CHEM., 34,(1991) N, C. 1302-1307

  摘要：

  DOI：

文献信息

• Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
  申请人：CHEN Han-Min

  公开号：US20140303112A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

  本发明涉及一种治疗疾病或病情的方法，该疾病或病情容易通过AMPK激活剂和公式化合物得到改善，这些化合物有助于激活AMP激活蛋白激酶（AMPK），并将这些化合物用于预防或治疗疾病，包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
• Structure-activity relationships of N2-substituted guanines as inhibitors of HSV1 and HSV2 thymidine kinases
  作者：Catherine Hildebrand、Daniele Sandoli、Federico Focher、Joseph Gambino、Giovanni Ciarrocchi、Silvio Spadari、George Wright

  DOI：10.1021/jm00163a033

  日期：1990.1

  A series of N2-phenylguanines was synthesized and tested for inhibition of the thymidine kinases encoded by Herpes simplex viruses type 1 and type 2. Compounds with hydrophobic, electron-attracting groups in the meta position of the phenyl ring such as m-trifluoromethyl (m-CF3PG, IC50 = 0.1 microM) were the most potent inhibitors of both enzymes. Many derivatives were significantly more potent against the type 2 thymidine kinase, and can effectively discriminate between the two enzymes. Among other N2-substituted guanines, alkyl and benzyl derivatives were moderately potent inhibitors, and the type 2 enzyme was again more sensitive than the type 1 enzyme. None of the compounds inhibited the thymidine kinase isolated from the host HeLa cell line, suggesting that members of this class of compounds may be useful nonsubstrate, antiviral compounds for latent herpesvirus infections.
• NOONAN, TIMOTHY;BROWN, NEAL;DUDYCZ, LECH;WRIGHT, GEORGE, J. MED. CHEM., 34,(1991) N, C. 1302-1307
  作者：NOONAN, TIMOTHY、BROWN, NEAL、DUDYCZ, LECH、WRIGHT, GEORGE

  DOI：——

  日期：——
• US9938279B2
  申请人：——

  公开号：US9938279B2

  公开（公告）日：2018-04-10
• Interaction of GTP derivatives with cellular and oncogenic ras-p21 proteins
  作者：Timothy Noonan、Neal Brown、Lech Dudycz、George Wright

  DOI：10.1021/jm00108a010

  日期：1991.4

  A series of N2-substituted guanosine 5'-triphosphates was synthesized from the corresponding nucleosides. The nucleosides were prepared by treatment of N2-substituted guanines with tetra-O-acetylribose under conditions which maximized the yield of the 9-beta-guanosine isomers. These nucleotides and several sugar- and base-modified analogues of GTP were tested for their ability to bind to cellular and oncogenic forms of the GTP/GDP binding proteins, Ha-ras-p21. Several N2-substituted GTPs showed affinities higher than that of GDP itself, and the N2-[p-(n-butyl)phenyl] derivative bound to the oncogenic mutant, Leu-61 p21, twice as strongly as to the cellular protein. Changes in relative affinities of the nucleotides are discussed with reference to reported crystallographic structures of p21.