3,5-dihydroxybenzylamine hydrobromide | 63720-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,5-dihydroxybenzylamine hydrobromide
• 英文别名: 5-(Aminomethyl)benzene-1,3-diol hydrobromide；5-(aminomethyl)benzene-1,3-diol;hydrobromide
• CAS: 63720-39-8
• 化学式: BrH*C₇H₉NO₂
• 分子量: 220.066
• InChiKey: HLTLUJVJGKYDEP-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.5
• 氢给体数：
  4
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3,5-dihydroxybenzylamine hydrobromide 、 氯乙酰氯 以50%的产率得到
  参考文献：
  名称：

  IKEDA M.; HIRAO K.; OKUNO Y.; NUMAO N.; YONEMITSU O., TETRAHEDRON , 1977, 33, NO 5, 489-495

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲氧基苄胺 、 氢溴酸 生成 3,5-dihydroxybenzylamine hydrobromide
  参考文献：
  名称：

  IKEDA M.; HIRAO K.; OKUNO Y.; NUMAO N.; YONEMITSU O., TETRAHEDRON , 1977, 33, NO 5, 489-495

  摘要：

  DOI：

文献信息

• Preparation, biological activity and endogenous occurrence of N6-benzyladenosines
  作者：Karel Doležal、Igor Popa、Eva Hauserová、Lukáš Spíchal、Kuheli Chakrabarty、Ondřej Novák、Vladimír Kryštof、Jiří Voller、Jan Holub、Miroslav Strnad

  DOI：10.1016/j.bmc.2007.03.038

  日期：2007.6

  Cytokinin activity of forty-eight 6-benzyladenosine derivatives at both the receptor and cellular levels as well as their anticancer properties were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine riboside with corresponding substituted benzylamines and characterized by standard collection of physico-chemical methods. The majority of synthesized derivatives exhibited high activity in all three of the cytokinin bioassays used (tobacco callus, wheat leaf senescence and Amaranthus bioassay). The highest activities were observed in the senescence bioassay. For several of the compounds tested, significant differences in activity were found between the bioassays used, indicating that diverse recognition systems may operate. This suggests that it may be possible to modulate particular cytokinin-dependent processes with specific compounds. In contrast to their high activity in bioassays, the tested compounds were recognized with only very low sensitivity in both Arabidopsis thaliana AHK3 and AHK4 receptor assays. The prepared derivatives were also investigated for their antiproliferative properties on cancer and normal cell lines. Several of them showed very strong cytotoxic activity against various cancer cell lines. On the other hand, they were not cytotoxic for normal murine fibroblast (NIH/3T3) cell line. This anticancer activity of cytokinin ribosides may be important, given that several of them occur as endogenous compounds in different organisms. (c) 2007 Elsevier Ltd. All rights reserved.
• Preparation and biological activity of 6-benzylaminopurine derivatives in plants and human cancer cells
  作者：Karel Doležal、Igor Popa、Vladimír Kryštof、Lukáš Spíchal、Martina Fojtíková、Jan Holub、René Lenobel、Thomas Schmülling、Miroslav Strnad

  DOI：10.1016/j.bmc.2005.09.004

  日期：2006.2

  To study the structure-activity relationships of aromatic cytokinins, the cytokinin activity at both the receptor and cellular levels, as well as CDK inhibitory and anticancer properties of 38 6-benzylaminopurine (BAP) derivatives were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine with corresponding substituted benzylamines. The majority of synthesised derivatives exhibited high activity in all three of the cytokinin bioassays employed (tobacco callus, wheat senescence and Amaranthus bioassay). The highest activities were obtained in the senescence bioassay. For some compounds tested, significant differences of activity were found in the bioassays used, indicating that diverse recognition systems may operate and suggesting that it may be possible to modulate particular cytokinin-dependent processes with specific compounds. Position-specific steric and hydrophobic effects of different phenyl ring substituents on the variation of biological activity were confirmed. In contrast to their high activity in bioassays, the BAP derivatives were recognised with much lower sensitivity than trans-zeatin in both Arabidopsis thaliana AHK3 and AHK4 receptor assays. The compounds were also investigated for their effects on cyclin-dependent kinase 2 (CDK2) and for antiproliferative properties on cancer and normal cell lines. Several of the tested compounds showed stronger inhibitory activity and cytotoxicity than BAP. There was also a significant positive correlation of the inhibitory effects on human and plant CDKs with cell proliferation of cancer and cytokinin-dependent tobacco cells, respectively. This suggests that at least a part of the antiproliferative effect of the new cytokinins was due to the inhibition of CDK activity. (c) 2005 Elsevier Ltd. All rights reserved.