α-dunnione | 83156-01-8

• 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: α-dunnione
• 英文别名: 2,3,3-trimethyl-2H-benzo[f][1]benzofuran-4,9-dione
• CAS: 83156-01-8
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: XWPLFOWMVZGBOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-hydroxy-3-(2-methylbut-3-en-2-yl)naphthalene-1,2-dione 在 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以45 mg的产率得到α-dunnione
  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

• 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。
• Quinones of streptocarpus dunnii
  作者：Kenichiro Inoue、Shinichi Ueda、Hidekazu Nayeshiro、Hiroyuki Inouyet

  DOI：10.1016/s0031-9422(00)86973-3

  日期：1983.1

  Abstract From the mature plants, plantlets and cultured cells coexisting with half differentiated plantlets of Streptocarpus dunnii , five unusually prenylated naphthoquinones and one anthraquinone were newly isolated along with both dunnione and 1-hydroxy-2-hydroxymethylanthraquinone, which had already been found in this plant. Furthermore, the structures of four new naphthoquinones, dehydrodunnione

  摘要 从 Streptocarpus dunnii 的成熟植株、幼苗和与半分化小植株共存的培养细胞中，新分离出 5 种异戊二烯化萘醌和 1 种蒽醌，以及在该植物中已发现的 dunnione 和 1-羟基-2-羟甲基蒽醌。 . 此外，阐明了四种新的萘醌，脱氢杜宁酮、链卡酮、7-羟基杜宁酮和8-羟基杜宁酮的结构。讨论了杜宁酮衍生物的光学纯度。
• 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。
• NOVEL PHENANTHRENEQUINONE-BASED COMPOUND AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME FOR THE TREATMENT OR PREVENTION OF DISEASE INVOLVING METABOLIC SYNDROME
  申请人：Yoo Sang-Ku

  公开号：US20100137422A1

  公开（公告）日：2010-06-03

  Provided is a pharmaceutical composition for the treatment and/or prevention of disease involving metabolic syndromes, comprising (a) a therapeutically effective amount of a particular compound represented by Formula 1 as defined in the specification, or isomer, prodrug, or solvate or thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供了一种用于治疗和/或预防涉及代谢综合征的疾病的制药组合物，包括(a)根据规范中定义的公式1所代表的特定化合物的治疗有效量，或其异构体，前药或溶剂或其任意组合物，以及(b)药学上可接受的载体，稀释剂或赋形剂，或其任意组合物。