8-(phenylamino)caffeine | 313976-85-1

• 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: 8-(phenylamino)caffeine
• 英文别名: 8-anilino-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione；8-Anilino-1,3,7-trimethyl-3,7-dihydro-purin-2,6-dion；8-anilino-1,3,7-trimethylpurine-2,6-dione
• CAS: 313976-85-1
• 化学式: C₁₄H₁₅N₅O₂
• 分子量: 285.305
• InChiKey: WPNLZMXRXPPHHH-UHFFFAOYSA-N

物化性质

• 沸点：
  498.5±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(phenylamino)caffeine 在 sodium amide 、 N,N-二甲基甲酰胺 作用下， 生成 8-[N-(2-dimethylamino-ethyl)-anilino]-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  [碱取代的嘌呤衍生物。II]。

  摘要：

  DOI：

  10.1002/ardp.19572900103
• 作为产物：
  描述：

  8-溴-1,3,7-三甲基嘌呤-2,6-二酮 、 苯胺 生成 8-(phenylamino)caffeine
  参考文献：
  名称：

  8-取代黄嘌呤的合成及其氧化骨架重排为 1-Oxo-2,4,7,9-tetraazaspiro[4,5]dec-2-ene-6,8,10-triones

  摘要：

  描述了许多 8-（二烷基氨基）-和 8-烷氧基黄嘌呤（分别为 3 和 6）的合成。用间氯过氧苯甲酸 (m-CPBA) 处理 3，通过新的重排 3-(二取代氨基)-4,7,9-trimethyl-1-oxo-2,4,7,9-tetraazaspiro[4,5 ]dec-2-ene-6,8,10-triones 10。此外，相应的 3-烷氧基取代的螺环化合物 12 是通过类似处理 8-烷氧基黄嘌呤 6 获得的。试图阐明这种重排的初步机制8-[(二烷基氨基)甲基]咖啡因 7 在用 m-CPBA 处理时没有发生重排，但只产生了预期的 N-氧化物衍生物 16。这个结果似乎表明发生这种重排的必要结构元素是一个原子将一对未共享的电子连接到所研究的黄嘌呤的 8 位。

  DOI：

  10.1002/(sici)1099-0690(199909)1999:9<2419::aid-ejoc2419>3.0.co;2-1

文献信息

• Compounds for repressing cancer cell growth
  申请人：Institute For Cancer Research

  公开号：US11203598B2

  公开（公告）日：2021-12-21

  The disclosure generally relates to compounds, compositions, and methods for the treatment of cancer by restoring the P53 pathway signaling to repress cancer cell growth. In particular, the compounds comprise Formula I: or a pharmaceutically acceptable salt thereof, wherein: R1 is hydrogen or a haloalkyl group; and each R2, R3, R4, R5, R6, and R7 is, independently, hydrogen, halogen, hydroxyl, cyano, alkyl, alkenyl, alkoxy, substituted or unsubstituted aryl, heteroaryl, phosphate, phosphoramidate, amine, alkylamino, acylamino, aminoalkoxy, or alkylthio.

  本公开一般涉及通过恢复 P53 通路信号抑制癌细胞生长来治疗癌症的化合物、组合物和方法。特别是，这些化合物包括式 I： 或其药学上可接受的盐，其中R1 是氢或卤代烷基；R2、R3、R4、R5、R6 和 R7 各自独立地是氢、卤素、羟基、氰基、烷基、烯基、烷氧基、取代或未取代的芳基、杂芳基、磷酸、磷酰胺、胺、烷基氨基、酰基氨基、氨基烷氧基或烷硫基。
• Lueppo-Cramer, Chemische Berichte, 1894, vol. 27, p. 3090
  作者：Lueppo-Cramer

  DOI：——

  日期：——
• Thio- and aminocaffeine analogues as inhibitors of human monoamine oxidase
  作者：Hermanus P. Booysen、Christina Moraal、Gisella Terre’Blanche、Anél Petzer、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.bmc.2011.10.036

  日期：2011.12

  In a recent study it was shown that 8-benzyloxycaffeine analogues act as potent reversible inhibitors of human monoamine oxidase (MAO) A and B. Although the benzyloxy side chain appears to be particularly favorable for enhancing the MAO inhibition potency of caffeine, a variety of other C8 oxy substituents of caffeine also lead to potent MAO inhibition. In an attempt to discover additional C8 substituents of caffeine that lead to potent MAO inhibition and to explore the importance of the ether oxygen for the MAO inhibition properties of C8 oxy-substituted caffeines, a series of 8-sulfanyl-and 8-aminocaffeine analogues were synthesized and their human MAO-A and -B inhibition potencies were compared to those of the 8-oxycaffeines. The results document that the sulfanylcaffeine analogues are reversible competitive MAO-B inhibitors with potencies comparable to those of the oxycaffeines. The most potent inhibitor, 8-[(4-bromophenyl)methyl]sulfanyl}caffeine, exhibited an IC50 value of 0.167 mu M towards MAO-B. While the sulfanylcaffeine analogues also exhibit affinities for MAO-A, they display in general a high degree of MAO-B selectivity. The aminocaffeine analogues, in contrast, proved to be weak MAO inhibitors with a number of analogues exhibiting no binding to the MAO-A and -B isozymes. The results of this study are discussed with reference to possible binding orientations of selected caffeine analogues within the active site cavities of MAO-A and -B. MAO-B selective sulfanylcaffeine derived inhibitors may act as lead compounds for the design of antiparkinsonian therapies. (C) 2011 Elsevier Ltd. All rights reserved.
• Compounds For Repressing Cancer Cell Growth
  申请人：Institute For Cancer Research d/b/a The Research Institute Of Fox Chase Cancer Center

  公开号：US20190225613A1

  公开（公告）日：2019-07-25

  The disclosure generally relates to compounds, compositions, and methods for the treatment of cancer by restoring the P53 pathway signaling to repress cancer cell growth.