N¹-(pyrene-1-ylmethyl)-1,4-diaminobutane dihydrochloride | 127856-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N¹-(pyrene-1-ylmethyl)-1,4-diaminobutane dihydrochloride
• 英文别名: N'-(pyren-1-ylmethyl)butane-1,4-diamine;hydrochloride
• CAS: 127856-48-8
• 化学式: C₂₁H₂₂N₂*2ClH
• 分子量: 375.341
• InChiKey: HXDQHGQQKKJNLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [4-[(pyrene-1-yl)amino]butyl]carbamic acid tert-butyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到N¹-(pyrene-1-ylmethyl)-1,4-diaminobutane dihydrochloride
  参考文献：
  名称：

  Amine−Guanidine Switch: A Promising Approach to Improve DNA Binding and Antiproliferative Activities

  摘要：

  A series of polyaromatic guanidino derivatives was synthesized and evaluated for growth inhibitory properties in several human carcinoma cell lines. The properties of these guanidino compounds were compared to those of their corresponding synthetic amino precursors. The size of the polyaromatic ring system as well as the length of the tether attached to the ring had a direct impact on the observed antiproliferative profiles, compound 14 having the broadest spectrum of activity. As both series intercalate DNA, guanidine derivatives showed a remarkable affinity for DNA and the guanidinium group appeared to be essential, yet not sufficient for caspase-3/7 activation. Compound 14 also showed significant in vivo activity against breast cancer cell xenografts in NOG/SCID mice. These results suggest that the electronic nature of chain tethering an intercalator not only influences the DNA-binding process but also controls the antitumoral activity of the whole compound.

  DOI：

  10.1021/jm701207m