naphtho[1,2-b]thiophene-5,6-dicarboxylic anhydride | 676542-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: naphtho[1,2-b]thiophene-5,6-dicarboxylic anhydride
• 英文别名: 3-Oxa-11-thiatetracyclo[7.6.1.05,16.010,14]hexadeca-1(16),5,7,9,12,14-hexaene-2,4-dione
• CAS: 676542-48-6
• 化学式: C₁₄H₆O₃S
• 分子量: 254.266
• InChiKey: WDIOEEDZBPRCRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-[bis(2-aminoethyl)]-N,N'-dimethyl-1,3-propanediamine 、 naphtho[1,2-b]thiophene-5,6-dicarboxylic anhydride 以 乙醇 、 甲苯 为溶剂， 反应 72.0h， 以28%的产率得到3-[2-[3-[2-(2,4-Dioxo-11-thia-3-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(16),5,7,9,12,14-hexaen-3-yl)ethyl-methylamino]propyl-methylamino]ethyl]-11-thia-3-azatetracyclo[7.6.1.05,16.010,14]hexadeca-1(16),5,7,9,12,14-hexaene-2,4-dione
  参考文献：
  名称：

  New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles:  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties

  摘要：

  Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a, pi -excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.

  DOI：

  10.1021/jm0308850
• 作为产物：
  描述：

  2-[(1-methoxycarbonyl)-2-(3-thienyl)vinyl]benzoic acid 在 碘 、 sodium hydroxide 、 sodium hydrogensulfite 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 8.25h， 以55%的产率得到naphtho[1,2-b]thiophene-5,6-dicarboxylic anhydride
  参考文献：
  名称：

  New Analogues of Amonafide and Elinafide, Containing Aromatic Heterocycles:  Synthesis, Antitumor Activity, Molecular Modeling, and DNA Binding Properties

  摘要：

  Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a, pi -excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.

  DOI：

  10.1021/jm0308850