6-hydroxy-2-isopropenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione

• 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: 6-hydroxy-2-isopropenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
• 英文别名: 6-hydroxy-dehydro-iso-β-lapachone；lantalucratin B；6-hydroxy-2-prop-1-en-2-yl-2,3-dihydrobenzo[g][1]benzofuran-4,5-dione
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: WKLGYQWVPPIRFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-dihydroxy-2-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione 在 硫酸 、 乙酸酐 、 三乙胺 、 potassium hydroxide 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 2.75h， 生成 6-hydroxy-2-isopropenyl-2,3-dihydronaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  QSAR on antiproliferative naphthoquinones based on a conformation-independent approach

  摘要：

  The antiproliferative activities of a series of 36 naphthoquinone derivatives were subjected to a Quantitative Structure Activity Relationships (QSAR) study. For this purpose a panel of four human cancer cell lines was used, namely HBL-100 (breast), HeLa (cervix), SW-1573 (non-small cell lung) and WiDr (colon). A conformation-independent representation of the chemical structure was established in order to avoid leading with the scarce experimental information on X-ray crystal structure of the drug interaction. The 1179 theoretical descriptors derived with E-Dragon and Recon software were simultaneously analyzed through linear regression models based on the Replacement Method variable subset selection technique. The established models were validated and tested through the use of external test sets of compounds, the Leave-One-Out Cross Validation method, Y-Randomization and Applicability Domain analysis. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.057

文献信息

• 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。
• Pharmaceutical composition for obesity, diabetes, metabolic syndrome, neuro-degenerative diseases and mitochondria dysfunction diseases
  申请人：Md Bioalpha Co., Ltd.

  公开号：EP2532390A2

  公开（公告）日：2012-12-12

  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.

  本发明提供了一种用于治疗和预防肥胖症、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的药物组合物，该药物组合物包含：治疗有效量的下式 I 所代表的化合物，或其药学上可接受的盐、原药、溶媒或异构体，以及药学上可接受的载体、稀释剂或赋形剂，或其任意组合。
• Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization
  作者：Tokutaro Ogata、Yoshiko Sugiyama、Saki Ito、Kazuha Nakano、Eri Torii、Arisa Nishiuchi、Tetsutaro Kimachi

  DOI：10.1016/j.tet.2013.09.081

  日期：2013.12

  The first total synthesis of (+/-)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (+/-)-lantalucratins A and B in excellent yield with complete regioselectivity. The 1,2-naphthoquinone fused five-membered cyclic ether framework was constructed directly from 3-hydroxyallcyl-naphthalenes by oxidative intramolecular cyclization reaction with diammonium cerium(IV) nitrate. (+/-)-Lantalucratins A and B were obtained in 69% and 45% overall yields, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

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