benzofuran-4,5-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzofuran-4,5-dione
• 英文别名: 4,5-benzofurandione；1-Benzofuran-4,5-dione
• 化学式: C₈H₄O₃
• 分子量: 148.118
• InChiKey: OWRQRCNVZWAHAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  benzofuran-4,5-dione 、 2,3-二甲基-1,3-丁二烯 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 甲苯 为溶剂， 反应 3.0h， 生成 7,8-dimethylnaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

  摘要：

  In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b] furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control beta-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H... pi interactions with Trp105 and Phe178 residues compared to the control beta-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.004
• 作为产物：
  描述：

  5-苯并呋喃 在 2-碘酰基苯甲酸 作用下， 以 水 为溶剂， 生成 benzofuran-4,5-dione
  参考文献：
  名称：

  Discovery of quinone-directed antitumor agents selectively bioactivated by NQO1 over CPR with improved safety profile

  摘要：

  In this work, we mainly focused on discovering compounds with good selectivity for NQO1 over CPR. The NQO1-mediated two-electron reduction of compounds would kill cancer cells selectively, while CPR-mediated one-electron reduction would induce potential hepatotoxicity. Several novel quinone-directed antitumor agents were discovered as specific NQO1 substrates through structure-activity relationship studies. Among them, compound 3,7,8-trimethylnaphtho[1,2-b] furan-4,5-dione (12b) emerged as the most specific substrate of the two-electron oxidoreductase NQO1 and could hardly be reduced by CPR. It afforded the highest selectivity between NQO1/CPR (selectivity ratio = 6.37), much higher than the control beta-lapachone (selectivity ratio = 1.36), indicated 12b may possess superior safety profile. The electrochemical studies provided a reasonable explanation to the good selectivity toward NQO1. Molecular docking studies supported that 12b was capable of forming additional C-H... pi interactions with Trp105 and Phe178 residues compared to the control beta-lap. In addition, compound 12b was shown to kill cancer cells efficiently both in vitro and in vivo model. This work gave us a promising and novel scaffold for further investigation. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.004

文献信息

• [EN] BENZOFURAN-4,5-DIONES AS SELECTIVE PEPTIDE DEFORMYLASE INHIBITORS<br/>[FR] BENZOFURANE-4-5-DIONES CONSTITUANT DES INHIBITEURS SÉLECTIFS DE LA DÉFORMYLASE DE PEPTIDE
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2010129049A1

  公开（公告）日：2010-11-11

  The instant invention provides novel benzofuran-4,5-diones and pharmaceutical compositions thereof useful for inhibiting PDF and for treating proliferative and infectious diseases. Compounds may be selective for eukaryotic (e.g., human) PDF or prokaryotic PDF.

  本发明提供了新型的苯并呋喃-4,5-二酮及其药物组合物，用于抑制PDF并治疗增殖性和感染性疾病。这些化合物可能对真核生物（例如，人类）PDF或原核生物PDF具有选择性。
• PHARMACEUTICAL COMPOSITION FOR THE TREATMENT AND PREVENTION OF DISEASES INVOLVING IMPOTENCE
  申请人：Kwak Taehwan

  公开号：US20100239674A1

  公开（公告）日：2010-09-23

  Disclosed is a pharmaceutical composition for the treatment and/or prevention of erectile dysfunction, comprising (a) a therapeutically effective amount of a compound represented by Formula 1 or 2, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  本发明公开了一种用于治疗和/或预防勃起功能障碍的药物组合物，包括（a）按照式1或式2表示的化合物的治疗有效量，以及（b）药学上可接受的载体、稀释剂或赋形剂，或其任意组合。
• Pharmaceutical Composition for the Treatment or Prevention of Diseases Involving Obesity, Diabetes, Metabolic Syndrome, Neuro-Degenerative Diseases and Mitochondria Dyfunction Diseases
  申请人：Yoo Sang-Ku

  公开号：US20080146655A1

  公开（公告）日：2008-06-19

  Provided is a pharmaceutical composition for the treatment and prevention of obesity, diabetes, metabolic syndromes, degenerative diseases and mitochondrial dysfunction-related diseases, comprising: a therapeutically effective amount of a compound represented by Formula I below, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供一种药物组合物，用于治疗和预防肥胖、糖尿病、代谢综合征、退行性疾病和线粒体功能障碍相关疾病，包括：以下式I所表示的化合物的治疗有效量，或其药学上可接受的盐、前药、溶剂或异构体，以及药学上可接受的载体、稀释剂或赋形剂，或其任意组合。
• PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OR PREVENTION OF DISEASES INVOLVING OBESITY, DIABETES, METABOLIC SYNDROME, NEURO-DEGENERATIVE DISEASES AND MITOCHONDRIA DYSFUNCTION DISEASES
  申请人：Yoo Sang-Ku

  公开号：US20090292011A1

  公开（公告）日：2009-11-26

  Provided is a pharmaceutical composition for the treatment and prevention of obesity, diabetes, metabolic syndromes, degenerative diseases and mitochondrial dysfunction-related diseases, comprising: a therapeutically effective amount of a compound represented by Formula I below, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供了一种用于治疗和预防肥胖、糖尿病、代谢综合征、退行性疾病以及线粒体功能障碍相关疾病的制药组合物，包含以下公式I所表示的化合物的治疗有效量，或其药学上可接受的盐、前药、溶剂或异构体，以及药学上可接受的载体、稀释剂或赋形剂，或任何组合。
• BENZOFURAN-4,5-DIONES AS SELECTIVE PEPTIDE DEFORMYLASE INHIBITORS
  申请人：Djaballah Hakim

  公开号：US20120071523A1

  公开（公告）日：2012-03-22

  The instant invention provides novel benzofuran-4,5-diones and pharmaceutical compositions thereof useful for inhibiting PDF and for treating proliferative and infectious diseases. Compounds may be selective for eukaryotic (e.g., human) PDF or prokaryotic PDF.

  该发明提供了新颖的苯并呋喃-4,5-二酮及其制备的药物组合物，可用于抑制PDF并治疗增殖性和传染性疾病。化合物可以选择性地作用于真核生物（例如人类）或原核生物的PDF。