[2-((1Z,4Z,9Z,15Z)-2,8,12,18-Tetraethyl-3,7,13,17-tetramethyl-15-{2-[4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyrylamino]-phenyl}-porphyrin-5-yl)-phenyl]-carbamic acid ethyl ester | 132255-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-((1Z,4Z,9Z,15Z)-2,8,12,18-Tetraethyl-3,7,13,17-tetramethyl-15-{2-[4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyrylamino]-phenyl}-porphyrin-5-yl)-phenyl]-carbamic acid ethyl ester
• CAS: 132255-35-7
• 化学式: C₅₆H₆₂N₈O₅
• 分子量: 927.159
• InChiKey: NGAVKWFUHRMDOI-FZJMBLERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.22
• 重原子数：
  69.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  179.65
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  氯甲酸乙酯 、 α,α-5,15-bis(2'-aminophenyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyrin 、 1-thyminebutanoic acid 在 吡啶盐酸盐 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 [2-((1Z,4Z,9Z,15Z)-2,8,12,18-Tetraethyl-3,7,13,17-tetramethyl-15-{2-[4-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyrylamino]-phenyl}-porphyrin-5-yl)-phenyl]-carbamic acid ethyl ester
  参考文献：
  名称：

  Hisatome, Masao; Maruyama, Noriaki; Furutera, Tetsuo, Chemistry Letters, 1990, # 12, p. 2251 - 2254

  摘要：

  DOI：

文献信息

• Synthesis and Some Spectroscopic Properties of Porphyrin Derivatives Connected with Nucleobases (Adenine, Thymine, Guanine and Cytosine) by Alkanamide Chains.
  作者：Masao HISATOME、Noriaki MARUYAMA、Koichi IKEDA、Tetsuo FURUTERA、Tomiyasu ISHIKAWA、Koji YAMAKAWA

  DOI：10.1248/cpb.44.1801

  日期：——

  Several kinds of porphyrin derivatives covalently connected with adenine, thymine, guanine, cytosine or adenine-thymine pair in a stacking mode between the porphyrin and nucleobase moiety have been synthesized via amide formation reaction of (2-aminophenyl)porphyrin derivatives with nucleobase-alkanoic acids, and characterized by spectroscopic methods. In the 1H-NMR spectra of these nucleobase-porphyrins the proton signals of the nucleobase moieties appear at remarkably higher fields than those of the reference compounds (the corresponding nucleobase-alkanoates) which have no porphyrin moiety. The behaviors of the high field shifts, due to the diamagnetic ring current effect of the porphyrin ring, reflect the characteristic conformational features of these compounds in which the base moieties are located at the upper zone of the porphyrin ring. The Soret bands of the porphyrin in the electronic absorption spectra were markedly weaker in intensity compared with those of the reference compound which has no nucleobase moiety. Both the high-field shifts of the base protons and the hypochromic effects on the Soret band are larger in guanine and cytosine systems than those in adenine and thymine systems, respectively.Those results indicate greater affinity of guanine and cytosine for porphyrin in comparison with adenine and cytosine, respectively, and this conclusion is compatible with the reported electronic spectral properties of mixtures of polynucleotides and water-soluble porphyrin derivatives.

  几种通过(2-氨基苯基)卟啉衍生物与核苷酸-烷酸通过酰胺形成反应共价连接的卟啉衍生物已被合成，这些核苷酸包括腺嘌呤、胸腺嘧啶、鸟嘌呤、胞嘧啶或腺嘌呤-胸腺嘧啶对，并且以堆叠模式与卟啉和核苷酸部分相连。合成的化合物通过光谱方法进行了表征。在这些核苷酸-卟啉的1H-NMR光谱中，核苷酸部分的质子信号出现在明显高于参考化合物（对应的核苷酸-烷酸酯，也没有卟啉部分）的化学位移位置。这种高场位移的行为源于卟啉环的抗磁环流效应，反映了这些化合物的特征构象特征，其中碱基部分位于卟啉环的上方。在电子吸收光谱中，卟啉的索雷特带的强度明显弱于不含核苷酸部分的参考化合物。与腺嘌呤和胸腺嘧啶系统相比，鸟嘌呤和胞嘧啶系统中的碱基质子的高场位移和对索雷特带的弱化效应更为显著。这些结果表明，与腺嘌呤和胸腺嘧啶相比，鸟嘌呤和胞嘧啶对卟啉有更强的亲和力，这一结论与已报道的聚核苷酸和水溶性卟啉衍生物混合物的电子光谱特性相符。