2,5-dihydroxy-7-methyl-1,4-naphthoquinone | 39058-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,5-dihydroxy-7-methyl-1,4-naphthoquinone
• 英文别名: 2-Hydroxy-7-methyl-juglon
• CAS: 39058-20-3
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: KVXSFHXUTPSVOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,5-dihydroxy-7-methyl-1,4-naphthoquinone 、 乙酸酐 在 溶剂黄146 、 锌 作用下， 生成 7-methylnaphthalene-1,2,4,5-tetra-O-acetate
  参考文献：
  名称：

  Lillie,T.J.; Musgrave,O.C., Journal of the Chemical Society. Perkin transactions I, 1977, p. 355 - 359

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(2-羟基-4-甲基苯基)-4-氧代丁酸 在 盐酸 、 sodium hydroxide 、 三氯化铝 、 PPA 、 amalgamated zinc 、 乙醇 、 硫酸 、 甲苯 、 sodium chloride 作用下， 生成 2,5-dihydroxy-7-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  425.真菌化学研究。第五部分2：5-二羟基-7-甲基-1：4-萘醌的合成

  摘要：

  DOI：

  10.1039/jr9560002173

文献信息

• Catalyst‐Controlled Transannular Polyketide Cyclization Cascades: Selective Folding of Macrocyclic Polyketides
  作者：Felix C. Raps、Vincent C. Fäseke、Daniel Häussinger、Christof Sparr

  DOI：10.1002/ange.202005733

  日期：2020.10.12

  biomimetic synthesis of aromatic polyketides from macrocyclic substrates by means of catalyst‐controlled transannular cyclization cascades is described. The macrocyclic substrates, which feature increased stability and fewer conformational states, were thereby transformed into several distinct polyketide scaffolds. The catalyst‐controlled transannular cyclizations selectively led to aromatic polyketides with

  摘要描述了通过催化剂控制的跨环环化级联从大环底物仿生合成芳香族聚酮化合物。大环底物具有更高的稳定性和更少的构象状态，因此被转化为几种不同的聚酮化合物支架。催化剂控制的跨环环化选择性地产生具有明确折叠和氧化模式的芳香族聚酮化合物，从而模拟聚酮化合物生物合成的β-酮加工步骤。
• Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase
  作者：Anita Mahapatra、Sannah P.N. Mativandlela、B. Binneman、P.B. Fourie、Chris J. Hamilton、J.J.M. Meyer、F. van der Kooy、Peter Houghton、Namrita Lall

  DOI：10.1016/j.bmc.2007.08.064

  日期：2007.12

  The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plant-derived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e. g. other disulfide reductases). (c) 2007 Elsevier Ltd. All rights reserved.
• Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines
  作者：Navneet Kishore、Brigitte Binneman、Anita Mahapatra、Maryna van de Venter、Debbie du Plessis-Stoman、Gerhardt Boukes、Peter Houghton、J.J. Marion Meyer、Namrita Lall

  DOI：10.1016/j.bmc.2014.06.013

  日期：2014.9

  In an effort to establish new candidates with enhanced anticancer activity of 5-hydroxy-7-methyl-1,4-naphthoquinone scaffold (7-methyljuglone) previously isolated from the root extract of Euclea natalensis, a series of 7-methyljuglone derivatives have been synthesized and assessed for cytotoxicity on selected human cancer lines. These compounds were screened in vitro for anticancer activity on MCF-7, HeLa, SNO and DU145 human cancer cell lines by MTT assay. Most of them exhibited significant toxicity on cancer cell lines with lower IC50 values. The most potent derivative (19) exhibited the toxicity on HeLa and DU145 cell lines with IC50 value of 5.3 and 6.8μM followed by compound (5) with IC50 value of 10.1 and 9.3μM, respectively. Structure-activity relationship reveals that the fluoro substituents at position C-8 while hydroxyl substituents at C-2 and C-5 positions played an important role in toxicity.
• Lillie, Terence J.; Musgrave, Oliver C., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1161 - 1164
  作者：Lillie, Terence J.、Musgrave, Oliver C.

  DOI：——

  日期：——
• [EN] SKIN BONDING PROCESS<br/>[FR] PROCESSUS D'ADHESION CUTANEE
  申请人：UNIV CREIGHTON

  公开号：WO2006107827A1

  公开（公告）日：2006-10-12

  [EN] The present invention relates to methods of providing a desired effect to the skin of a mammal using a Maillard initiating reagent with a skin-modifying compound.
  [FR] La présente invention concerne des procédés permettant d'obtenir un effet souhaité sur la peau d'un mammifère en utilisant une réaction de Maillard avec un composé modifiant la peau.