9-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b]indol-4-ylamine | 56344-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 9-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b]indol-4-ylamine
• 英文别名: 9-Phenyl-6,7,8,9-tetrahydro-5H-1,3,9-triaza-fluoren-4-ylamine；9-phenyl-5,6,7,8-tetrahydropyrimido[4,5-b]indol-4-amine
• CAS: 56344-59-3
• 化学式: C₁₆H₁₆N₄
• 分子量: 264.33
• InChiKey: ZBIUNPVYINOLQB-UHFFFAOYSA-N

物化性质

• 熔点：
  219-220 °C(Solv: ethanol (64-17-5))
• 沸点：
  412.1±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b]indol-4-ylamine 在 palladium on activated charcoal 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以52%的产率得到9-phenyl-9H-pyrimido<4,5-b>indole-4-amine
  参考文献：
  名称：

  Eger, Kurt; Lanzner, Wolfgang; Rothenhaeusler, Klaus, Liebigs Annalen der Chemie, 1993, # 5, p. 465 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-1-苯基-4,5,6,7-四氢吲哚-3-甲腈 、 甲酰胺 生成 9-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b]indol-4-ylamine
  参考文献：
  名称：

  MULLER, CHRISTA E.;HIDE, IZUMI;DALY, JOHN W.;ROTHENHAUSLER, KLAUS;EGER, K+, J. MED. CHEM., 33,(1990) N0, C. 2822-2828

  摘要：

  DOI：

文献信息

• 7-Deaza-2-phenyladenines: structure-activity relationships of potent A1 selective adenosine receptor antagonists
  作者：Christa E. Mueller、Izumi Hide、John W. Daly、Klaus Rothenhaeusler、Kurt Eger

  DOI：10.1021/jm00172a023

  日期：1990.10

  A series of derivatives of 7-deazapurines with varying substituents in the 2-, 6-, and 9-position was synthesized in an attempt to improve the adenosine receptor affinity and A1 or A2 selectivity. The adenosine receptor affinities were assessed by measuring the inhibition of [3H]-(R)-N6-(phenylisopropyl) adenosine (R-PIA) binding to rat brain A1 and inhibition of [3H]-5'-(N-ethylcarboxamido)adenosine (NECA) binding to rat striatum A2 adenosine receptors. A selected set of compounds representing the main structural variations was further examined in adenosine receptor coupled adenylate cyclase assays. All tested compounds antagonized the inhibition of adenylate cyclase elicited by interaction of R-PIA with A1 receptors in rat fat cell membranes and the activation of adenylate cyclase elicited by interaction of NECA with A2 receptors of pheochromocytoma PC12 cell membranes. The results indicate that 7-deazahypoxanthines have a potential for A2 selectivity, while all 7-deazaadenines are A1 selective. Introduction of a phenyl residue in the 2-position of 7-deazaadenines increases A1 activity tremendously. 2-(p-Chlorophenyl)-7,8-dimethyl-9-phenyl-7-deazaadenine (29) is potent and specific for the A1 receptors of rat brain (Ki = 122 nM), having no affinity for the A2 receptors of rat striatum. The compound has low activity at the A2 receptors of rat PC12 cell membranes where it appears to act as a noncompetitive inhibitor. A 1-phenylethyl substituent at the 9-position was found to be superior to a phenyl residue in terms of A1 affinity. The most potent A1 antagonist in the present series is the highly A1 selective (790-fold) (R)-7,8-dimethyl-2-phenyl-9-(1-phenylethyl)-7-deazaadenine (31, Ki = 4.7 nM), which is 30-35 times more potent at A1 receptors than its S enantiomer. The solubility of six of the potent 7-deaza-2-phenyladenines was determined by means of an A1 binding assay. Chloro substitution of the 2-phenyl ring appeared to improve the solubility as well as the solubility over A1 affinity ratio of 9-phenyl- and 9-(1-phenylethyl)-substituted 7-deazadenines.
• MULLER, CHRISTA E.;HIDE, IZUMI;DALY, JOHN W.;ROTHENHAUSLER, KLAUS;EGER, K+, J. MED. CHEM., 33,(1990) N0, C. 2822-2828
  作者：MULLER, CHRISTA E.、HIDE, IZUMI、DALY, JOHN W.、ROTHENHAUSLER, KLAUS、EGER, K+

  DOI：——

  日期：——
• Eger Kurt, Lanzner Wolfgang, Rothenhaeusler Klaus, Liebigs Ann. Chem., (1993) N 5, S 465-470
  作者：Eger Kurt, Lanzner Wolfgang, Rothenhaeusler Klaus

  DOI：——

  日期：——
• Eger, Kurt; Lanzner, Wolfgang; Rothenhaeusler, Klaus, Liebigs Annalen der Chemie, 1993, # 5, p. 465 - 470
  作者：Eger, Kurt、Lanzner, Wolfgang、Rothenhaeusler, Klaus

  DOI：——

  日期：——