9,10-bis[N-(aminoethylene)aminomethyl]anthracene | 108365-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis[N-(aminoethylene)aminomethyl]anthracene
• 英文别名: N'-[[10-[(2-aminoethylamino)methyl]-9-anthryl]methyl]ethane-1,2-diamine；N'-[[10-[(2-aminoethylamino)methyl]anthracen-9-yl]methyl]ethane-1,2-diamine
• CAS: 108365-96-4
• 化学式: C₂₀H₂₆N₄
• 分子量: 322.453
• InChiKey: DUOBHOQMGPIAHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吡啶-2,6-二甲醛 、 9,10-bis[N-(aminoethylene)aminomethyl]anthracene 以 乙醇 为溶剂， 反应 12.0h， 以76%的产率得到
  参考文献：
  名称：

  Highly Selective Recognition and Fluorescence Imaging of Adenosine Polyphosphates in Aqueous Solution

  摘要：

  The design and synthesis of chemosensors for the recognition of a certain nucleoside polyphosphate among various structurally similar nucleoside polyphosphates remain a fundamental challenge. Herein, we report the new fluorescent chemosensor [Zn2L](ClO4)(4) (1; L = (3,6,10,13,17,20,24,27-octaaza-1,15(2,6)-dipyridina-8,22(9,10)-dianthracenacyclooctacosaphane), which can selectively recognize adenosine polyphosphates (ATP and ADP) among various nucleoside polyphosphates, with a large fluorescence enhancement (F-max/F-0 = 70 and 80 for ATP and ADP, respectively) and strong binding affinity (K = 3.1 x 10(11) M-1 for [Zn2HL(H(-1)ATP)(2)](-), 2.8 x 10(11) M-1 for [Zn2L(H(-1)ATP)(2)](2-), and 1.5 x 10(13) M-1 for [Zn2L(H(-1)ADP)(2)](2-)) in aqueous solution at physiological pH 7.40. The structure of [Zn2L] (P2O7) (2) was investigated, which shows that mu(2)-pyrophosphate anions alternately link [Zn2L](4+) cations to generate a 1D coordination polymer. The results of P-31 NMR studies and DFT calculations reveal that the two Zn(II) ions in 1 can interact with ATP/ADP anions through coordination interactions between Zn(II) and the polyphosphate groups, and two anthracene moieties in I can interact with adenine groups from two ATP or ADP anions through stacking interactions to form a sandwichlike structure. These multiple recognition interactions between 1 and ATP/ADP enhance the affinity and selectivity of 1, toward ATP/ADP. Due to its highly selective and sensitive ability to detect adenosine polyphosphates, 1 was successfully applied to fluorescence imaging for ATP and ADP in living cells, demonstrating the potential utility of 1 as a fluorescent chemosensor for detecting ATP and ADP.

  DOI：

  10.1021/ic302435g
• 作为产物：
  描述：

  9,10-二(氯甲基)蒽 、 乙二胺 以 甲苯 为溶剂， 反应 6.0h， 生成 9,10-bis[N-(aminoethylene)aminomethyl]anthracene
  参考文献：
  名称：

  含有蒽核的新型抗肿瘤药。

  摘要：

  合成了21种与比索汀有关的新化合物，并通过针对各种人类肿瘤细胞系，新鲜人类肿瘤和P-388白血病的克隆形成测定法进行了体外测试。与bisantrene最密切相关的那些化合物的活性低于其活性，但是具有饱和侧链的含两个碱性氮的化合物子集显示出良好的活性。此子集的两个化合物，N，N'-双[2-（二甲基氨基）乙基] -9,10-蒽双（甲胺）（6）和N，N'-双（1-乙基-3-哌啶基）- 9,10-蒽二（甲胺）（19）在体外对人肿瘤细胞系非常活跃，但对新鲜的人肿瘤或P-388白血病细胞没有活性。它们在小鼠肿瘤模型中仅具有边缘活性。从而，对于体内这些蒽化合物在体内对抗小鼠肿瘤的活性，新鲜的人类肿瘤和体外P-388白血病细胞比已建立的细胞系更好地预测。在作用方式方面，这些化合物似乎与比桑蒽不同。例如，6在细胞毒性药物浓度下不会引起大分子合成的抑制和DNA单链断裂的促进。毒理学研究表明，快速给药引起急性神

  DOI：

  10.1021/jm00391a009

文献信息

• Crystal structures of three host–guest complexes of methylsubstituted cucurbit[6]urils and anthracene derivatives
  作者：Ze-Hua Chen、Fa-Geng Zhou、Yun-Qian Zhang、Qian-Jiang Zhu、Sai-Feng Xue、Zhu Tao

  DOI：10.1016/j.molstruc.2009.05.005

  日期：2009.7

  methylsubstituted cucurbit[6]urils host and anthracene derivatives guests were synthesized and structurally characterized by single crystal X-ray diffractions and 1 H NMR technique. The hosts are dodecamethylcucurbit[6]uril (DDMeQ[6]), α,α′,δ,δ′-tetramethylcucurbit[6]uril (TMeQ[6]), and hexa-methylsubstituted cucurbituril (HSMeQ[6]) made from 3a-methyl-glycoluril. The guests are 9,10-bis[ N -(aminoe

  摘要 合成了三种甲基取代的葫芦[6]脲主体和蒽衍生物客体的主客体配合物，并通过单晶X射线衍射和1 H NMR技术对其进行了结构表征。宿主是十二甲基葫芦脲 [6] 脲 (DDMeQ[6])、α,α',δ,δ'-四甲基葫芦脲 [6] 脲 (TMeQ[6]) 和六甲基取代葫芦脲 (HSMeQ[6]) 3a-甲基甘脲。客体是9,10-双[N-(氨基亚乙基)氨基甲基]蒽(AN1)、9,10-双[N-(氨基亚丙基)氨基甲基]蒽(AN2)和9,10-双[N-(氨基丁烯)氨甲基]蒽（AN3）。晶体结构显示化合物 1-3 的化学计量为 DDMeQ[6]-AN1} 2+ 2NO 3 − 24H 2 O ( 1 ), TMeQ[6]-AN2} 2+ 4NO 3 − 2H 3 O + 10H 2 O ( 2 ) 和 2HSMeQ[6]-AN3} 2+ 2Cl − 25H 2 O ( 3 )，
• WUNZ, TIMOTHY P.;DORR, ROBERT T.;ALBERTS, DAVID S.;TUNGET, CYNTHIA L.;EIN+, J. MED. CHEM., 30,(1987) N 8, 1313-1321
  作者：WUNZ, TIMOTHY P.、DORR, ROBERT T.、ALBERTS, DAVID S.、TUNGET, CYNTHIA L.、EIN+

  DOI：——

  日期：——