3-chloro-7-ethyl-5,6,8-trihydroxy-2-methoxy-1,4-naphthoquinone | 880154-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-chloro-7-ethyl-5,6,8-trihydroxy-2-methoxy-1,4-naphthoquinone
• 英文别名: hydroxychloronaphthazarin；7-Chloro-3-ethyl-2,5,8-tri-hydroxy-6-methoxy-1,4-naphthoquinone；2-chloro-6-ethyl-5,7,8-trihydroxy-3-methoxynaphthalene-1,4-dione
• CAS: 880154-58-5
• 化学式: C₁₃H₁₁ClO₆
• 分子量: 298.68
• InChiKey: KVXUVLJWNHOBFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-chloro-7-ethyl-5,6,8-trihydroxy-2-methoxy-1,4-naphthoquinone 在 sodium azide 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 3-amino-7-ethyl-5,8-dihydroxy-2,6-dimethoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilis

  摘要：

  It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone)-the first marine aminated hydroxynaphthazarin, a metabolite of the sea urchin Scaphechinus mirabilis (Agassiz). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.109
• 作为产物：
  描述：

  2,3-dichloro-7-ethyl-6-hydroxynaphthazarin 在 sodium azide 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-chloro-7-ethyl-5,6,8-trihydroxy-2-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilis

  摘要：

  It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone)-the first marine aminated hydroxynaphthazarin, a metabolite of the sea urchin Scaphechinus mirabilis (Agassiz). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.109

文献信息

• Biochemical and Genomic Characterization of the Cypermethrin-Degrading and Biosurfactant-Producing Bacterial Strains Isolated from Marine Sediments of the Chilean Northern Patagonia
  作者：Patricia Aguila-Torres、Jonathan Maldonado、Alexis Gaete、Jaime Figueroa、Alex González、Richard Miranda、Roxana González-Stegmaier、Carolina Martin、Mauricio González

  DOI：10.3390/md18050252

  日期：——

  Pesticides cause severe environmental damage to marine ecosystems. In the last ten years, cypermethrin has been extensively used as an antiparasitic pesticide in the salmon farming industry located in Northern Patagonia. The objective of this study was the biochemical and genomic characterization of cypermethrin-degrading and biosurfactant-producing bacterial strains isolated from cypermethrin-contaminated marine sediment samples collected in southern Chile (MS). Eleven strains were isolated by cypermethrin enrichment culture techniques and were identified by 16S rDNA gene sequencing analyses. The highest growth rate on cypermethrin was observed in four isolates (MS13, MS15a, MS16, and MS19) that also exhibited high levels of biosurfactant production. Genome sequence analyses of these isolates revealed the presence of genes encoding components of bacterial secondary metabolism, and the enzymes esterase, pyrethroid hydrolase, and laccase, which have been associated with different biodegradation pathways of cypermethrin. These novel cypermethrin-degrading and biosurfactant-producing bacterial isolates have a biotechnological potential for biodegradation of cypermethrin-contaminated marine sediments, and their genomes contribute to the understanding of microbial lifestyles in these extreme environments.

  杀虫剂对海洋生态系统造成严重环境破坏。在过去的十年里，氯氰菊酯广泛被用作北巴塔哥尼亚的三文鱼养殖业中的抗寄生虫杀虫剂。本研究的目标是对从智利南部收集的氯氰菊酯污染海洋沉积物样品中分离出的降解氯氰菊酯和产生生物表面活性剂的细菌菌株进行生化和基因组特征化。通过氯氰菊酯富集培养技术分离出11株菌株，并通过16S rDNA基因测序分析进行鉴定。在氯氰菊酯上观察到最高生长率的是四株分离物（MS13、MS15a、MS16和MS19），它们还表现出较高水平的生物表面活性剂产生。这些分离物的基因组序列分析显示存在编码细菌次生代谢组分、酯酶、拟除虫菊酯水解酶和漆酶的基因，这些基因与氯氰菊酯的不同生物降解途径有关。这些新型降解氯氰菊酯和产生生物表面活性剂的细菌分离物具有生物降解氯氰菊酯污染海洋沉积物的生物技术潜力，它们的基因组有助于理解这些极端环境中微生物生活方式。
• Inspired by Sea Urchins: Warburg Effect Mediated Selectivity of Novel Synthetic Non-Glycoside 1,4-Naphthoquinone-6S-Glucose Conjugates in Prostate Cancer
  作者：Sergey A. Dyshlovoy、Dmitry N. Pelageev、Jessica Hauschild、Yurii E. Sabutskii、Ekaterina A. Khmelevskaya、Christoph Krisp、Moritz Kaune、Simone Venz、Ksenia L. Borisova、Tobias Busenbender、Vladimir A. Denisenko、Hartmut Schlüter、Carsten Bokemeyer、Markus Graefen、Sergey G. Polonik、Victor Ph. Anufriev、Gunhild von Amsberg

  DOI：10.3390/md18050251

  日期：——

  cells is known as Warburg effect. It results from a high glycolysis rate, used by tumors as preferred metabolic pathway even in aerobic conditions. Targeting the Warburg effect to specifically deliver sugar conjugated cytotoxic compounds into tumor cells is a promising approach to create new selective drugs. We designed, synthesized, and analyzed a library of novel 6-S-(1,4-naphthoquinone-2-yl)-d-glucose

  肿瘤细胞高糖消耗的现象被称为Warburg效应。它来自高糖酵解速率，即使在有氧条件下，也被肿瘤用作首选的代谢途径。靶向Warburg效应以将糖缀合的细胞毒性化合物特异地递送至肿瘤细胞是创建新的选择性药物的一种有前途的方法。我们设计，合成和分析了海胆1,4-萘醌类似物的新型6-S-（1,4-萘醌-2-基）-d-葡萄糖嵌合分子（SABs）-新糖缀合物的文库以前曾显示出抗癌特性的颜料Spinochromes。硫接头（硫醚键）用于防止人糖苷非特异性酶潜在的水解作用。合成的化合物对人前列腺癌细胞（包括高度耐药细胞系）表现出Warburg效应介导的选择性。线粒体被确定为SAB的主要细胞靶标。作用机制包括线粒体膜通透性，ROS上调和细胞毒性线粒体蛋白（AIF和细胞色素C）释放到细胞质中，导致随后的caspase-9和-3活化，PARP裂解和凋亡样细胞死亡。这些结果使我们能够进一步临床开发这些化合物，以有
• Reaction of echinochrome trimethyl ether with aqueous ammonia
  作者：G. I. Mel’man、V. A. Denisenko、V. Ph. Anufriev

  DOI：10.1007/s11172-010-0312-z

  日期：2010.9

  Reaction of 7-ethyl-2,3,6-trimethoxynaphthazarin with NH3·H2O proceeds at the carbonyl groups at the C(4) atoms of the 1,4-naphthoquinonoid tautomeric forms. Methoxy group adjacent to ethyl group is the orienting substituent in this reaction.

  7-乙基-2,3,6-trimethoxynaphthazarin 与 NH3·H2O 的反应在 1,4-naphthoquinonoid 互变异构形式的 C(4) 原子的羰基处进行。与乙基相邻的甲氧基是该反应中的定向取代基。
• Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A—a metabolite produced by the sea urchin Scaphechinus mirabilis
  作者：Nataly D. Pokhilo、Alla Ya. Yakubovskaya、Vladimir A. Denisenko、Victor Ph. Anufriev

  DOI：10.1016/j.tetlet.2005.12.109

  日期：2006.2

  It was found that 6-hydroxy- and 6-alkoxy-2,3-dichloronaphthazarins react smoothly with sodium azide in methanol to produce the corresponding 2-azido derivatives as single regioisomers. We have explored the utility of this reaction for the synthesis of echinamine A (3-amino-7-ethyl-2,5,6,8-tetrahydroxy-1,4-naphthoquinone)-the first marine aminated hydroxynaphthazarin, a metabolite of the sea urchin Scaphechinus mirabilis (Agassiz). (c) 2006 Elsevier Ltd. All rights reserved.