7,8,9,10-tetrahydrobenzo[d]naphtho[1,2-b]furan-5,6-dione | 654066-90-7

• 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: 7,8,9,10-tetrahydrobenzo[d]naphtho[1,2-b]furan-5,6-dione
• 英文别名: 7,8,9,10-Tetrahydronaphtho[1,2-b][1]benzofuran-5,6-dione
• CAS: 654066-90-7
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: NSWLRMHKQBEWPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,8,9,10-tetrahydrobenzo[d]naphtho[1,2-b]furan-5,6-dione 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 5.0h， 以40%的产率得到benzo[b]naphtho[2,1-d]furan-5,6-dione
  参考文献：
  名称：

  A Facile Method for the Synthesis of Dihydrofuranonaphthoquinones, Furanonaphthoquinones, and Benzofuranonaphthoquinones

  摘要：

  An efficient synthesis of dihydrofuranonaphthoquinone, furanonaphthoquinone, and benzonaphthoquinone derivatives has been carried out starting from 2-hydroxy-1,4-naphthoquinone and a variety of vinyl sulfides in moderate yields.

  DOI：

  10.1081/scc-120026354
• 作为产物：
  描述：

  1-(phenylthio)cyclohex-1-ene 在 ammonium cerium(IV) nitrate 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 间二甲苯 、 乙腈 为溶剂， 反应 36.0h， 生成 7,8,9,10-tetrahydrobenzo[d]naphtho[1,2-b]furan-5,6-dione
  参考文献：
  名称：

  A Facile Method for the Synthesis of Dihydrofuranonaphthoquinones, Furanonaphthoquinones, and Benzofuranonaphthoquinones

  摘要：

  An efficient synthesis of dihydrofuranonaphthoquinone, furanonaphthoquinone, and benzonaphthoquinone derivatives has been carried out starting from 2-hydroxy-1,4-naphthoquinone and a variety of vinyl sulfides in moderate yields.

  DOI：

  10.1081/scc-120026354

文献信息

• Tandem Synthesis of Furanaphthoquinones via Enamines and Evaluation of Their Antiparasitic Effects against Trypanosoma cruzi
  作者：Mariana Cardoso、Luana Forezi、Acácio de Souza、Ana Faria、Raissa Galvão、Murilo Bello、Fernando da Silva、Robson Faria、Vitor Ferreira

  DOI：10.21577/0103-5053.20210142

  日期：——

  Furanaphthoquinones are well known in medicinal chemistry for exhibiting relevant structural heterogeneity and bioactivities. In this work, it was synthesized a series of furanaphthoquinones through a tandem reaction between lawsone (8) and cyclic ketones in the presence of morpholine. This strategy provides an efficient and general method for synthesizing furanaphthoquinones with activity against the epimastigote form of Trypanosoma cruzi (T. cruzi), the parasite that causes Chagas disease. Compound 9b was the better prototype, and it exhibited high potency for causing parasite death, showed reduced acute toxicity towards mammalian cells, and was capable of rupturing the epimastigote plasma membrane and acting on sterol 14α-demethylase (CYP51). Additionally, 9b reduced trypomastigote viability by 99% after 24 h. Candidate 9b demonstrated the best and most promising profile when bound to CYP51.

  呋喃萘醌在药物化学中以其结构异质性和生物活性而闻名。本研究通过在吗啡催化下，将罗孚酮（8）和环状酮串联反应合成了一系列呋喃萘醌。该策略为合成对克氏锥虫表皮螺旋体形式（T. cruzi）具有活性的呋喃萘醌提供了一种高效而通用的方法，该寄生虫会导致查加斯病。化合物9b是更好的原型，它表现出高效的寄生虫死亡作用，对哺乳动物细胞的急性毒性减少，并能够破坏表皮螺旋体细胞膜并作用于甾体14α-去甲基酶（CYP51）。此外，9b在24小时内将试螺旋体细胞的活力降低了99%。候选物9b在与CYP51结合时表现出最佳和最有前途的特征。
• The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones
  作者：Suyou Liu、Lijun Long、Duoduo Xie、Lijun Liu、Dayou Ma

  DOI：10.1016/j.tetlet.2015.10.058

  日期：2015.12

  Naphthofuroquinones are of great value in medicinal chemistry. In this letter, a facile method for highly regioselective synthesis of both linear and angular naphthofuroquinones has been developed via iodine mediated cyclization of 2-hydroxy-3-substitutedvinyl-1,4-naphthoquinones under very mild conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• A Facile Method for the Synthesis of Dihydrofuranonaphthoquinones, Furanonaphthoquinones, and Benzofuranonaphthoquinones
  作者：Yong Rok Lee、Byung So Kim

  DOI：10.1081/scc-120026354

  日期：2003.12.1

  An efficient synthesis of dihydrofuranonaphthoquinone, furanonaphthoquinone, and benzonaphthoquinone derivatives has been carried out starting from 2-hydroxy-1,4-naphthoquinone and a variety of vinyl sulfides in moderate yields.