2-oxo-2H-thieno(2,3-H)(1)-benzopyran-3-carboxylic acid methyl ester | 74458-97-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-oxo-2H-thieno(2,3-H)(1)-benzopyran-3-carboxylic acid methyl ester
• 英文别名: Wtnblxzkpnjcph-uhfffaoysa-；methyl 2-oxothieno[2,3-h]chromene-3-carboxylate
• CAS: 74458-97-2
• 化学式: C₁₃H₈O₄S
• 分子量: 260.27
• InChiKey: WTNBLXZKPNJCPH-UHFFFAOYSA-N

物化性质

• 熔点：
  >180 °C
• 沸点：
  472.8±45.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-oxo-2H-thieno(2,3-H)(1)-benzopyran-3-carboxylic acid methyl ester 在 喹啉 、 盐酸 、 水 、 铜 、 溶剂黄146 作用下， 反应 27.0h， 生成 Thieno[2,3-h]chromen-2-one
  参考文献：
  名称：

  Synthesis of angelicin heteroanalogues: preliminary photobiological and pharmacological studies

  摘要：

  A series of angelicin heteroanalogues, in which the furan was replaced by thiophene or a 1-substituted pyrazole moiety, was synthesised in order to obtain potential therapeutic agents with antiproliferative and/or other biological activities. In general, the antiproliferative activity of the new thioangelicin, tested in different biological substrates, appeared to be higher than that of the angelicin, the natural parent compound, but lower than that of 8-MOP, the furocoumarin ordinarily used in PUVA therapy and photopheresis. Thioangelicin 6 induced strong inhibition of T2 bacteriophage infectivity and was able to significantly repress the DNA. synthesis in Ehrlich ascites cells and the clonal growth in HeLa cells. The pyrazolocoumarins did not show any noticeable effect upon UVA irradiation in all the biological systems considered. All the new angelicin heteroanalogues appeared to be free of the known phototoxicity of furocoumarins on the skin. The pyrazolocoumarins have also been tested as anti-inflammatory, analgesic, antipyretic, local anaesthetic, anti-arrhythmic and platelet antiaggregating agents by standard procedures. In this class of derivatives, 10a showed good anti-inflammatory and antipyretic properties, while 9a and 11a showed significant local anaesthetic activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00076-7
• 作为产物：
  描述：

  4-hydroxy-benzo[b]thiophene-5-carbaldehyde 在 盐酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-oxo-2H-thieno(2,3-H)(1)-benzopyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Asprou, Chris M.; Brunskill, John S. A.; Jeffrey, Howard, Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 87 - 92

  摘要：

  DOI：

文献信息

• ASPROU C. M.; BRUNSKILL J. S. A.; JEFFREY H.; DE A., J. HETEROCYCL. CHEM., 1980, 17, NO 1, 87-92
  作者：ASPROU C. M.、 BRUNSKILL J. S. A.、 JEFFREY H.、 DE A.

  DOI：——

  日期：——
• Asprou, Chris M.; Brunskill, John S. A.; Jeffrey, Howard, Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 87 - 92
  作者：Asprou, Chris M.、Brunskill, John S. A.、Jeffrey, Howard、De, Asish

  DOI：——

  日期：——
• Synthesis of angelicin heteroanalogues: preliminary photobiological and pharmacological studies
  作者：Luisa Mosti、Eleonora Lo Presti、Giulia Menozzi、Christine Marzano、Francarosa Baccichetti、Giuseppe Falcone、Walter Filippelli、Brunella Piucci

  DOI：10.1016/s0014-827x(98)00076-7

  日期：1998.8

  A series of angelicin heteroanalogues, in which the furan was replaced by thiophene or a 1-substituted pyrazole moiety, was synthesised in order to obtain potential therapeutic agents with antiproliferative and/or other biological activities. In general, the antiproliferative activity of the new thioangelicin, tested in different biological substrates, appeared to be higher than that of the angelicin, the natural parent compound, but lower than that of 8-MOP, the furocoumarin ordinarily used in PUVA therapy and photopheresis. Thioangelicin 6 induced strong inhibition of T2 bacteriophage infectivity and was able to significantly repress the DNA. synthesis in Ehrlich ascites cells and the clonal growth in HeLa cells. The pyrazolocoumarins did not show any noticeable effect upon UVA irradiation in all the biological systems considered. All the new angelicin heteroanalogues appeared to be free of the known phototoxicity of furocoumarins on the skin. The pyrazolocoumarins have also been tested as anti-inflammatory, analgesic, antipyretic, local anaesthetic, anti-arrhythmic and platelet antiaggregating agents by standard procedures. In this class of derivatives, 10a showed good anti-inflammatory and antipyretic properties, while 9a and 11a showed significant local anaesthetic activity. (C) 1998 Elsevier Science S.A. All rights reserved.

表征谱图