3-phenylbenzothiopheno[2,3-c]pyran-1-one | 1155888-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-phenylbenzothiopheno[2,3-c]pyran-1-one
• 英文别名: 3-phenyl-1H-[1]benzothieno[2,3-c]pyran-1-one；3-Phenyl-[1]benzothiolo[2,3-c]pyran-1-one
• CAS: 1155888-02-0
• 化学式: C₁₇H₁₀O₂S
• 分子量: 278.331
• InChiKey: LUXKMRSSSFAGEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴苯并噻吩-2-羧酸 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以40%的产率得到3-phenylbenzothiopheno[2,3-c]pyran-1-one
  参考文献：
  名称：

  Synthesis of novel 3-(aryl)benzothieno[2,3-c]pyran-1-ones from Sonogashira products and intramolecular cyclization: Antitumoral activity evaluation

  摘要：

  Several novel 3-(aryl)benzothieno[2,3-c]pyran-1-ones (tricyclic lactones) were prepared either by a tandem one-pot Sonogashira coupling and intramolecular cyclization, reacting the 3-bromobenzo[b]thiophene-2-carboxylic acid with arylacetylenes, or by Sonogashira coupling of the methyl 3-bromobenzo[b]thiophene-2-carboxylate or the methyl 3-bromo-6-methoxybenzo[b]thiophene-2-carboxylate with arylacetylenes followed by an electrophilic intramolecular cyclization using iodine or TFA in two separate steps. The Sonogashira products and the tricyclic lactones obtained were evaluated for their capacity to inhibit the in vitro growth of three human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer). Most of the compounds showed a high growth inhibitory effect on all the tested cell lines, with GI(50) values in the mu M range. A structure-activity relationship was established for the Sonogashira products and for the tricyclic lactones, namely related to the presence and position of substituents (OMe and/or F) in the benzothiophene moiety or in the phenyl ring. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.002

文献信息

• Pd/ligand-free synthesis of thienopyranones via Cu-catalyzed coupling-cyclization in PEG 400 under ultrasound
  作者：Manam Sreenivasa Rao、Meda Haritha、N. Chandrasekhar、Mandava V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2014.01.115

  日期：2014.2

  A greener and practical synthesis of 5-substituted thieno[2,3-c]pyran-7-ones has been achieved via Cu-catalyzed coupling-cyclization of 3-iodothiophene-2-carboxylic acid with terminal alkynes in the presence of K2CO3 in PEG 400 under ultrasound irradiation. A range of thienopyranone derivatives were synthesized by using this inexpensive and Pd- and ligand-free methodology. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of novel 3-(aryl)benzothieno[2,3-c]pyran-1-ones from Sonogashira products and intramolecular cyclization: Antitumoral activity evaluation
  作者：Maria-João R.P. Queiroz、Ricardo C. Calhelha、Luís A. Vale-Silva、Eugénia Pinto、M. São-José Nascimento

  DOI：10.1016/j.ejmech.2008.11.002

  日期：2009.5

  Several novel 3-(aryl)benzothieno[2,3-c]pyran-1-ones (tricyclic lactones) were prepared either by a tandem one-pot Sonogashira coupling and intramolecular cyclization, reacting the 3-bromobenzo[b]thiophene-2-carboxylic acid with arylacetylenes, or by Sonogashira coupling of the methyl 3-bromobenzo[b]thiophene-2-carboxylate or the methyl 3-bromo-6-methoxybenzo[b]thiophene-2-carboxylate with arylacetylenes followed by an electrophilic intramolecular cyclization using iodine or TFA in two separate steps. The Sonogashira products and the tricyclic lactones obtained were evaluated for their capacity to inhibit the in vitro growth of three human tumor cell lines, MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer). Most of the compounds showed a high growth inhibitory effect on all the tested cell lines, with GI(50) values in the mu M range. A structure-activity relationship was established for the Sonogashira products and for the tricyclic lactones, namely related to the presence and position of substituents (OMe and/or F) in the benzothiophene moiety or in the phenyl ring. (C) 2008 Elsevier Masson SAS. All rights reserved.