2-formylbenzo[b]thiophene-4,7-quinone | 474310-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-formylbenzo[b]thiophene-4,7-quinone
• 英文别名: 4,7-Dioxo-1-benzothiophene-2-carbaldehyde；4,7-dioxo-1-benzothiophene-2-carbaldehyde
• CAS: 474310-38-8
• 化学式: C₉H₄O₃S
• 分子量: 192.195
• InChiKey: KPLKZZSHLQIBTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-euryfuran 、 2-formylbenzo[b]thiophene-4,7-quinone 以 溶剂黄146 为溶剂， 反应 3.0h， 以47%的产率得到4,7-Dioxo-5-((5aS,9aS)-6,6,9a-trimethyl-4,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-3-yl)-4,7-dihydro-benzo[b]thiophene-2-carbaldehyde
  参考文献：
  名称：

  Studies on Quinones. Part 38: synthesis and leishmanicidal activity of sesquiterpene 1,4-Quinones

  摘要：

  The reaction of (+)-euryfuran 1 with several benzo-, naphtho- and benzo[b]thiophene-1,4-quinones in acetic acid yields the corresponding euryfuryl-1.4-quinones 3, 5, 7, 8, 10, 12, and 14. The structure of compounds 7, 8, 12, and 14 was assigned through 2D NMR H-1-C-13 HMBC experiments. The influence of the acidity of the solvent upon the reactivity and regioselectivity of the quinones to the oxidative coupling reaction, is discussed. The in vitro activity of the euryfurylquinones and their corresponding precursors against Leishmania amazonensis is described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.011
• 作为产物：
  描述：

  4,7-dimethoxybenzo[b]thiophene-2-carbaldehyde 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到2-formylbenzo[b]thiophene-4,7-quinone
  参考文献：
  名称：

  Studies on Quinones. Part 38: synthesis and leishmanicidal activity of sesquiterpene 1,4-Quinones

  摘要：

  The reaction of (+)-euryfuran 1 with several benzo-, naphtho- and benzo[b]thiophene-1,4-quinones in acetic acid yields the corresponding euryfuryl-1.4-quinones 3, 5, 7, 8, 10, 12, and 14. The structure of compounds 7, 8, 12, and 14 was assigned through 2D NMR H-1-C-13 HMBC experiments. The influence of the acidity of the solvent upon the reactivity and regioselectivity of the quinones to the oxidative coupling reaction, is discussed. The in vitro activity of the euryfurylquinones and their corresponding precursors against Leishmania amazonensis is described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.011

文献信息

• Synthesis and Antitumor Evaluation of Thiophene Analogs of Kigelinone
  作者：Jaime Valderrama、Omar Espinoza、Jaime Rodriguez、Cristina Theoduloz

  DOI：10.2174/157017809788490006

  日期：2009.6.1

  The synthesis of kigelinone thiophene analogs and related naphtho[2,3-b]thiophene-4,9-quinones from 2- substituted 4,7-dimethoxybenzo[b]thiophenes via an oxidative deprotection, Diels-Alder, and oxidative aromatization reaction sequence is reported. The 2-substituted naphtho[2,3-b]thiophene-4,9-quinones display significant antitumor activity in the range IC50 1.1-47 μM on a panel of four distinct human

  由2-取代的4,7-二甲氧基苯并[b]噻吩经氧化脱保护，Diels-Alder和氧化芳构化反应顺序合成基基利农酮噻吩类似物和相关的萘并[2,3-b]噻吩-4,9-醌被报道。2-取代的萘并[2,3-b]噻吩-4,9-醌在一组四种不同的人类癌细胞系中的IC50范围为1.1-47μM时显示出显着的抗肿瘤活性。
• Synthesis and antiprotozoal activity of naphthofuranquinones and naphthothiophenequinones containing a fused thiazole ring
  作者：Ricardo A. Tapia、Luz Alegria、Carlos D. Pessoa、Cristian Salas、Manuel J. Cortés、Jaime A. Valderrama、Marie-Elisabeth Sarciron、Félix Pautet、Nadia Walchshofer、Houda Fillion

  DOI：10.1016/s0968-0896(03)00122-6

  日期：2003.5

  The synthesis of tetracyclic quinones 10a,b, 14a,b, 19a,b and 20a,b is described. The preparations involve regioselective Diels-Alder reactions via trapping the thiazole o-quinodimethane 9 with several benzofuranquinones and benzothiophenequinones. The structure of the regioisomers was assigned through 2D NMR H-1-C-13 HMBC experiments performed on 10a and 14a. Compounds 10a,b, 14a as well as phenol I and the starting quinones 2, 5, 7 and 15 are evaluated against Leishmania sp., Toxoplasma gondii and THP-1 cells. Almost all the tested compounds exhibit significant antiprotozoal activities with lower cytotoxicities than the reference compounds. Among them, quitiones 2 and 14a possess the best activities towards L. donovani and T. gondii with the lowest toxicities. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Studies on Quinones. Part 38: synthesis and leishmanicidal activity of sesquiterpene 1,4-Quinones
  作者：Jaime A Valderrama、Julio Benites、Manuel Cortés、Hernán Pessoa-Mahana、Eric Prina、Alain Fournet

  DOI：10.1016/j.bmc.2003.08.011

  日期：2003.11

  The reaction of (+)-euryfuran 1 with several benzo-, naphtho- and benzo[b]thiophene-1,4-quinones in acetic acid yields the corresponding euryfuryl-1.4-quinones 3, 5, 7, 8, 10, 12, and 14. The structure of compounds 7, 8, 12, and 14 was assigned through 2D NMR H-1-C-13 HMBC experiments. The influence of the acidity of the solvent upon the reactivity and regioselectivity of the quinones to the oxidative coupling reaction, is discussed. The in vitro activity of the euryfurylquinones and their corresponding precursors against Leishmania amazonensis is described. (C) 2003 Elsevier Ltd. All rights reserved.