5-O-benzoyl-2-methyl-1,4-naphthoquinone | 1471-98-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-O-benzoyl-2-methyl-1,4-naphthoquinone
• 英文别名: benzoate plumbagin；Plumbagin-benzoat；(6-Methyl-5,8-dioxo-1-naphthyl) benzoate；(6-methyl-5,8-dioxonaphthalen-1-yl) benzoate
• CAS: 1471-98-3
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: XMBVCTHCJZIZJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  兰雪醌 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以60 %的产率得到5-O-benzoyl-2-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  用于农药发现的天然产物：萘醌类白花丹和胡桃醌的结构多样性推导和生物活性

  摘要：

  病虫害严重影响农作物产量和品质，且难以防治。天然产物是发现新农药的重要来源。本工作以萘醌类白花红素和胡桃醌为母体结构，设计、合成了一系列衍生物，并对其杀菌活性、抗病毒活性和杀虫活性进行了评价。我们首次发现萘醌类化合物对14种真菌具有广谱抗真菌活性。一些萘醌显示出比嘧霉胺更高的杀真菌活性。化合物 I、I-1e 和 II-1a 作为新型抗真菌先导化合物出现，对花生尾孢属具有优异的杀真菌活性（EC50 值：11.35–17.70 µg/mL）。一些化合物还对烟草花叶病毒 (TMV) 表现出良好到极佳的抗病毒活性。化合物 I-1f 和 II-1f 显示出与利巴韦林相似水平的抗 TMV 活性，可作为新的抗病毒候选物。这些化合物还表现出良好到极好的杀虫活性。化合物 II-1d 和 III-1c 对小菜蛾的杀虫活性与苦参碱、氟虫隆和鱼藤酮相似。目前的研究发现了白花丹苷和胡桃醌作为母体结构，为它们在植物保

  DOI：

  10.3390/molecules28083328

文献信息

• Inhibition of Mycobacterial Growth by Plumbagin Derivatives
  作者：Ritta Mathew、Anil K. Kruthiventi、Jalli V. Prasad、Sadula P. Kumar、Garlapati Srinu、Dipankar Chatterji

  DOI：10.1111/j.1747-0285.2010.00987.x

  日期：——

  Electron transport and respiratory pathways are active in both latent and rapidly growing mycobacteria and remain conserved in all mycobacterial species. In mycobacteria, menaquinone is the sole electron carrier responsible for electron transport. Menaquinone biosynthesis pathway is found to be essential for the growth of mycobacteria. Structural analogs of the substrate or product of this pathway are found to be inhibitory for the growth of Mycobacterium smegmatis and M. tuberculosis. Several plumbagin [5‐hydroxy‐2‐methyl‐1, 4‐naphthaquinone] derivatives have been analyzed for their inhibitory effects of which butyrate plumbagin was found to be most effective on M. smegmatis mc2155, whereas crotonate plumbagin showed greater activity on M. tuberculosis H37Rv. Effect on electron transport and respiration was demonstrated by butyrate plumbagin inhibiting oxygen consumption in M. smegmatis. Structural modifications of these molecules can further be improved upon to generate new molecules against mycobacteria.
• ANTI-CANCER LEAD MOLECULE
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20140107196A1

  公开（公告）日：2014-04-17

  Derivatives of plumbagin can be selectively cytotoxic to breast cancer cells. Derivative ‘A’ (Acetyl Plumbagin) has emerged as a lead molecule for testing against estrogen positive breast cancer and has shown low hepatotoxicity as well as overall lower toxicity in nude mice model. The toxicity of derivative ‘A’ was determined to be even lower than vehicle control (ALT and AST markers). The possible mechanism of action identified based on the microarray experiments and pathway mapping shows that derivative ‘A’ could be acting by altering the cholesterol-related mechanisms. The low toxicity profile of derivative ‘A’ highlights its possible role'as future anti-cancer drug and/or as an adjuvant drug to reduce the toxicity of highly toxic chemotherapeutic'drugs.
• CHOLESTERYL ESTER TRANSFER PROTEIN (CETP) INHIBITION IN THE TREATMENT OF CANCER
  申请人：KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20180049997A1

  公开（公告）日：2018-02-22

  In one embodiment, the invention provides methods of treatment which use therapeutically effective amounts of Cholesteryl Ester Transfer Protein (CETP) inhibitors to treat a variety of cancers. In certain embodiments, the inhibitor is a CETP-inhibiting small molecule, CETP-inhibiting antisense oligonucleotide, CETP-inhibiting siRNA or a CETP-inhibiting antibody. Related pharmaceutical compositions, kits, diagnostics and screens are also provided.
• US9890106B2
  申请人：——

  公开号：US9890106B2

  公开（公告）日：2018-02-13
• [EN] CHOLESTERYL ESTER TRANSFER PROTEIN (CETP) INHIBITION IN THE TREATMENT OF CANCER<br/>[FR] INHIBITION DE PROTÉINE DE TRANSFERT D'ESTER DE CHOLESTÉRYLE (CETP) DANS LE TRAITEMENT DE CANCER
  申请人：KING ABDULLAH UNIV OF SCIENCE & TECH

  公开号：WO2016135633A1

  公开（公告）日：2016-09-01

  In one embodiment, the invention provides methods of treatment which use therapeutically effective amounts of Choleste ryl Ester Transfer Protein (CETP) inhibitors to treat a variety of cancers. In certain embodiments, the inhibitor is a CETP-inhibiting small molecule, CETP-inhibiting antisense oligonucleotide, CETP-inhibiting siRNA or a CETP- inhibiting antibody. Related pharmaceutical compositions, kits, diagnostics and screens are also provided.