2-氯-3-苯氧基萘-1,4-二酮 | 71369-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氯-3-苯氧基萘-1,4-二酮
• 英文名称: 2-chloro-3-phenoxynaphthalene-1,4-dione
• 英文别名: 2-Chloro-3-phenoxy-1,4-naphthoquinone
• CAS: 71369-17-0
• 化学式: C₁₆H₉ClO₃
• 分子量: 284.699
• InChiKey: QPTXRNYONDDBEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-3-苯氧基萘-1,4-二酮 在 bis-triphenylphosphine-palladium(II) chloride 、 cerium(III) chloride heptahydrate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 19.5h， 生成 N-(3-(2-chlorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Structure–activity relationships and colorimetric properties of specific probes for the putative cancer biomarker human arylamine N-acetyltransferase 1

  摘要：

  A naphthoquinone inhibitor of human arylamine N-acetyltransferase 1 (hNAT1), a potential cancer biomarker and therapeutic target, has been reported which undergoes a distinctive concomitant color change from red to blue upon binding to the enzyme. Here we describe the use of in silico modeling alongside structure-activity relationship studies to advance the hit compound towards a potential probe to quantify hNAT1 levels in tissues. Derivatives with both a fifty-fold higher potency against hNAT1 and a two-fold greater absorption coefficient compared to the initial hit have been synthesized; these compounds retain specificity for hNAT1 and its murine homologue mNat2 over the isoenzyme hNAT2. A relationship between pK(a), inhibitor potency and colorimetric properties has also been uncovered. The high potency of representative examples against hNAT1 in ZR-75-1 cell extracts also paves the way for the development of inhibitors with improved intrinsic sensitivity which could enable detection of hNAT1 in tissue samples and potentially act as tools for elucidating the unknown role hNAT1 plays in ER+ breast cancer; this could in turn lead to a therapeutic use for such inhibitors. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.03.015
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 生成 2-氯-3-苯氧基萘-1,4-二酮
  参考文献：
  名称：

  CLARK, N. G., PESTIC. SCI., 1984, 15, N 3, 235-240

  摘要：

  DOI：

文献信息

• New aryloxy‐quinone derivatives with promising activity on <i>Trypanosoma cruzi</i>
  作者：Christian Espinosa‐Bustos、Karina Vázquez、Javier Varela、Hugo Cerecetto、Margot Paulino、Rodrigo Segura、Jaime Pizarro、Brenda Vera、Mercedes González、Ana M. Zarate、Cristian O. Salas

  DOI：10.1002/ardp.201900213

  日期：2020.1

  with a program to develop new quinone derivatives as biologically active compounds, we designed and synthesized a new series of aryloxy‐quinones, which were evaluated in vitro against Trypanosoma cruzi in epimastigote form. Chemical modifications in three specific moieties on the aryloxy‐quinone core were considered for developing new anti‐T. cruzi agents. The majority of our new quinones showed higher

  继续开发新的醌衍生物作为生物活性化合物的计划，我们设计并合成了一系列新的芳氧基-醌，在体外对上鞭毛体形式的克氏锥虫进行了评估。芳氧基-醌核心上三个特定部分的化学修饰被考虑用于开发新的抗 T。克鲁兹特工。我们的大多数新醌显示出比硝呋莫司更高的效力（IC50 值 <0.70 µM），这是一种用作基线药物的已知药物（IC50 值为 7.00 µM）；然而，其中只有两种对 Vero 细胞的选择性高于硝呋莫司。构效关系分析提供了有关这些化合物的立体电子特征的信息，这些信息是增加锥虫活性的原因。使用药效团模型，我们绘制了杀锥虫活性的五种药效特征的替代模式。我们选择了 Epc1 化合物，发现与杀锥虫效果没有关系。这些结果为开发新的芳氧基-醌类化合物的结构特征提供了有用的信息，该化合物对原生动物寄生虫 T. cruzi 具有更高的效力。
• Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles
  作者：Vishnu K. Tandon、Hardesh K. Maurya

  DOI：10.1016/j.tetlet.2010.05.071

  日期：2010.7

  Unique nucleophilic substitution and addition reactions of nitrogen and sulfur nucleophiles with 1,4-quinones in aqueous suspension with amines and thiols have recently been demonstrated by us.2 However, the reactivity of oxygen nucleophiles toward nucleophilic substitution compared to nitrogen and sulfur nucleophiles ‘on water’ is not facile. An unprecedented economical, green methodology approach

  最近我们已经证明了氮和硫亲核体与1，4-醌在胺和硫醇的水悬浮液中的独特亲核取代和加成反应。2然而，与“在水上”的氮和硫亲核试剂相比，氧亲核试剂对亲核取代的反应性并不容易。已经证明了一种空前的经济，绿色方法学方法，该方法使用普通洗衣粉（LD；洗衣粉，0.5 mol％，可重复使用）/ SDS作为表面活性剂“在水中”，以优异的产率被1,4-醌中的氧亲核试剂亲核取代。
• Synthesis of 2-Alkoxy 1,4-Naphthoquinone Derivatives as Antiplatelet, Antiinflammatory, and Antiallergic Agents.
  作者：Jin-Cherng Lien、Li-Jiau Huang、Che-Ming Teng、Jih-Pyang Wang、Sheng-Chu Kuo

  DOI：10.1248/cpb.50.672

  日期：——

  In our continuing search for novel antiplatelet, antiallergic, and antiinflammatory agents, 2-alkoxy derivatives of 1,4-naphthoquinone were prepared. Some of these compounds showed significant antiplatelet, antiallergic, and antiinflammatory activities. Among them, 2-propoxy-1,4-naphthoquinone and 2-butoxy-1,4-naphthoquinone exhibited potent inhibitory effect on neutrophil superoxide anion formation

  在我们不断寻找新的抗血小板药，抗过敏药和抗炎药的过程中，制备了1,4-萘醌的2-烷氧基衍生物。这些化合物中的一些显示出显着的抗血小板，抗过敏和抗炎活性。其中，2-丙氧基-1,4-萘醌和2-丁氧基-1,4-萘醌对中性粒细胞超氧阴离子的形成具有有效的抑制作用。这两种化合物值得进一步探索。
• 一种铁催化醌类化合物氯化的方法
  申请人：南京师范大学

  公开号：CN114426441A

  公开（公告）日：2022-05-03

  本发明公开了一种铁催化醌类化合物氯化的方法，该方法包括如下步骤：在溶剂中，以氯化盐为氯试剂、过氧化物为氧化剂，铁为催化剂、氨基酸或其衍生物或新铜试剂为配体，氧化醌类化合物的烯键发生氯化反应生成氯取代的醌类化合物。本发明方法具有催化剂来源广泛、廉价和环保的优势；氧化剂来源广泛、廉价；氯化试剂温和、稳定和廉价；反应条件温和、选择性高和产率高；底物来源广泛且稳定；底物官能团相容性好且底物的适用范围广；天然产物也可以兼容，能很好的实现醌烯键上的氯化。在优化的反应条件之下，目标产品分离后产率可以高达90％。
• Micelles catalyzed chemoselective synthesis ‘in water’ and biological evaluation of oxygen containing hetero-1,4-naphthoquinones as potential antifungal agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Nripendra N. Mishra、Praveen K. Shukla

  DOI：10.1016/j.bmcl.2011.08.095

  日期：2011.11

  Various oxygen containing 1,4-naphthoquinone derivatives have been synthesized chemoselectively by an economical, viable green methodology approach using water as solvent with or without surfactants such as Triton X-100, SDS, LD (laundry detergent), and TBAB, a phase transfer catalyst and evaluated for their in vitro antifungal and antibacterial activity. The antifungal profile of 3, 4a, 4b, and 6 indicated that compounds 3a, 3b, 4b, 6a, and 6c have potent antifungal activity compared to clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Sporothrix schenckii, Trichophyton mentagraphytes, and Candida parapsilosis and compound 3b has been found to be a lead antifungal agent for further study. (C) 2011 Elsevier Ltd. All rights reserved.