1,4-Naphthoquinone, 2-(3,7-dimethyl-2,6-octadienyl)-3-hydroxy- | 57309-83-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,4-Naphthoquinone, 2-(3,7-dimethyl-2,6-octadienyl)-3-hydroxy-
• 英文别名: 2-hydroxy-3-geranyl-1,4-naphthoquinone；3-geranyllawsone
• CAS: 57309-83-8
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: WVKJMOFCZSHXHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-羟基-1,4-萘醌 、 geranyl bromide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 1,4-Naphthoquinone, 2-(3,7-dimethyl-2,6-octadienyl)-3-hydroxy-
  参考文献：
  名称：

  Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives

  摘要：

  A series of 17 selected natural and semisynthetic 1,4-naphthoquinones were synthesized, and their growth inhibitory activity was evaluated in vitro. The compounds were tested on six human cancer cell lines using the MTT colorimetric assay. The data revealed that of the chemicals under study only lapachol, its acetate and 3-geranyllawsone displayed the highest activity, recording mean IC50 values ranging from 15 to 22 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.049

文献信息

• Synthesis and Biological Evaluation of Lipophilic 1,4-Naphthoquinone Derivatives against Human Cancer Cell Lines
  作者：Shao-Hung Wang、Chih-Yu Lo、Zhong-Heng Gwo、Hong-Jhih Lin、Lih-Geeng Chen、Cheng-Deng Kuo、Jin-Yi Wu

  DOI：10.3390/molecules200711994

  日期：——

  these cell lines. Our results showed that the effectiveness of compound 11a may be attributed to its suppression of the survival of HT-29. Secondly, in the Hoechst 33258 staining test, compound 11a-treated cells exhibited nuclear condensation typical of apoptosis. Additionally, cell cycle analysis by flow cytometry indicated that compound 11a arrested HT-29 cells in the S phase. Furthermore, cell death

  为了检查疏水性对 1,4-萘醌衍生物抗癌活性的影响，合成并评估了一系列带有 2-O-烷基-、3-C-烷基-或 2/3-N-吗啉代烷基的化合物因其在体外对五种人类癌细胞系的抗癌活性。通过 MTT 测定法测定了这些衍生物对 HT-29、SW480、HepG2、MCF-7 和 HL-60 细胞的细胞毒性。其中，2-hydroxy-3-farnesyl-1,4-naphthoquinone (11a) 被发现对这些细胞系的细胞毒性最强。我们的结果表明，化合物 11a 的有效性可能归因于其抑制 HT-29 的存活。其次，在 Hoechst 33258 染色试验中，化合物 11a 处理的细胞表现出典型的细胞凋亡的核凝聚。此外，通过流式细胞术进行的细胞周期分析表明，化合物11a 在S 期阻止了HT-29 细胞。此外，通过膜联蛋白 V-FITC/碘化丙啶染色检测的细胞死亡表明，化合物 11a 以浓度依赖性方式有效诱导
• 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。
• PHARMACEUTICAL COMPOSITION FOR TREATMENT AND PREVENTION OF RESTENOSIS
  申请人：Kwak Taehwan

  公开号：US20100255054A1

  公开（公告）日：2010-10-07

  Provided is a pharmaceutical composition for the treatment and/or prevention of restenosis including (a) a therapeutically effective amount of a particular compound represented by Formula 1 and 2, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

  提供了一种药物组合物，用于治疗和/或预防再狭窄，包括(a) 一定量的化合物，其化学式为1和2，或其药学上可接受的盐、前药、溶剂或异构体，且具有治疗效果，以及(b) 药学上可接受的载体、稀释剂或赋形剂，或任何其组合。