9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid [8-(cis-3,5-(N,N-di-tert-butyloxycarbonyl)diaminocyclohexylamino)octyl]amide | 688790-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid [8-(cis-3,5-(N,N-di-tert-butyloxycarbonyl)diaminocyclohexylamino)octyl]amide
• CAS: 688790-73-0
• 化学式: C₃₉H₅₄N₄O₇
• 分子量: 690.88
• InChiKey: RTHKJZPPDUQICN-OUOZDZGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  151.93
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid [8-(cis-3,5-(N,N-di-tert-butyloxycarbonyl)diaminocyclohexylamino)octyl]amide 以 二氯甲烷 为溶剂， 以92%的产率得到9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid [8-(cis-3,5-(N,N-di-diaminocyclohexylamino)octyl)]amide tri(trifluoroacetate)
  参考文献：
  名称：

  Toward Efficient Zn(II)-Based Artificial Nucleases

  摘要：

  A series of cis-cis-triaminocyclohexane Zn(II) complex-anthraquinone intercalator conjugates, designed in such a way to allow their easy synthesis and modification, have been investigated as hydrolytic cleaving agents for plasmid DNA. The ligand structure comprises a triaminocyclohexane platform linked by means of alkyl spacers of different length (from C-4 to C-8) to the anthraquinone group which may intercalate the DNA. At a concentration of 5 muM, the complex of the derivative with a C-8 alkyl spacer induces the hydrolytic stand scission of supercoiled DNA with a rate of 4.6 x 10(-6) s(-1) at pH 7 and 37 degreesC. The conjugation of the metal complex with the anthraquinone group leads to a 15-fold increase of the cleavage efficiency when compared with the anthraquinone lacking Zn-triaminocyclohexane complex. The straightforward synthetic procedure employed, allowing a systematic change of the spacer length, made possible to gain more insight on the role of the intercalating group in determining the reactivity of the systems. Comparison of the reactivity of the different complexes shows a remarkable increase of the DNA cleaving efficiency with the length of the spacer. In the case of too-short spacers, the advantages due to the increased DNA affinity are canceled due to the incorrect positioning of the reactive group, thus leading to cleavage inhibition.

  DOI：

  10.1021/ja039465q
• 作为产物：
  描述：

  8-氨基-1-辛醇 在 palladium on activated charcoal 四溴化碳 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 235.0h， 生成 9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid [8-(cis-3,5-(N,N-di-tert-butyloxycarbonyl)diaminocyclohexylamino)octyl]amide
  参考文献：
  名称：

  Toward Efficient Zn(II)-Based Artificial Nucleases

  摘要：

  A series of cis-cis-triaminocyclohexane Zn(II) complex-anthraquinone intercalator conjugates, designed in such a way to allow their easy synthesis and modification, have been investigated as hydrolytic cleaving agents for plasmid DNA. The ligand structure comprises a triaminocyclohexane platform linked by means of alkyl spacers of different length (from C-4 to C-8) to the anthraquinone group which may intercalate the DNA. At a concentration of 5 muM, the complex of the derivative with a C-8 alkyl spacer induces the hydrolytic stand scission of supercoiled DNA with a rate of 4.6 x 10(-6) s(-1) at pH 7 and 37 degreesC. The conjugation of the metal complex with the anthraquinone group leads to a 15-fold increase of the cleavage efficiency when compared with the anthraquinone lacking Zn-triaminocyclohexane complex. The straightforward synthetic procedure employed, allowing a systematic change of the spacer length, made possible to gain more insight on the role of the intercalating group in determining the reactivity of the systems. Comparison of the reactivity of the different complexes shows a remarkable increase of the DNA cleaving efficiency with the length of the spacer. In the case of too-short spacers, the advantages due to the increased DNA affinity are canceled due to the incorrect positioning of the reactive group, thus leading to cleavage inhibition.

  DOI：

  10.1021/ja039465q