6,7-dichloro-5,8-dimethoxy-1,4-naphthoquinone | 51783-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,7-dichloro-5,8-dimethoxy-1,4-naphthoquinone
• 英文别名: 6,7-dichloro-5,8-dimethoxy-[1,4]naphthoquinone；6,7-Dichlor-5,8-dimethoxy-[1,4]naphthochinon；6,7-Dichlor-5,8-dimethoxy-1,4-naphthochinon；6,7-dichloro-5,8-dimethoxynaphthalene-1,4-dione
• CAS: 51783-53-0
• 化学式: C₁₂H₈Cl₂O₄
• 分子量: 287.099
• InChiKey: FCDAWNBJZQLHPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(N-carbomethoxyamino)-1-diazopropane 、 6,7-dichloro-5,8-dimethoxy-1,4-naphthoquinone 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 methyl 2-(6,7-dichloro-5,8-dimethoxybenz[f]indazol-4,9-dion-3-yl)-N-ethylcarbamate
  参考文献：
  名称：

  Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase

  摘要：

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.011
• 作为产物：
  描述：

  2,3-dichloro-5,8-dihydroxy-[1,4]naphthoquinone 、 碘甲烷 在 silver(l) oxide 作用下， 以 氯仿 为溶剂， 生成 6,7-dichloro-5,8-dimethoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Friedel-Crafts 与马来酸酐的缩合反应。三、多羟基萘醌类化合物的合成

  摘要：

  已发现氢醌醚与过量的二卤代马来酸酐的缩合产生特别好的二卤萘扎林产率。后者的醚化和nu...

  DOI：

  10.1139/v74-132

文献信息

• Discovery of 1,4-Naphthoquinones as a New Class of Antiproliferative Agents Targeting GPR55
  作者：Mariateresa Badolato、Gabriele Carullo、Maria Cristina Caroleo、Erika Cione、Francesca Aiello、Fabrizio Manetti

  DOI：10.1021/acsmedchemlett.8b00333

  日期：2019.4.11

  A new series of 1,4-naphthoquinones, bearing various cyclic and aliphatic amines on C2, was designed and synthesized to identify antiproliferative agents for triple-negative breast cancer, which represents a clinical challenge without targeted therapies. Among naphthoquinones, 2a and 3a inhibited the proliferation of MDA-MB-231 cells (EC50 = 1.6 and 2.7 μM, respectively), compared to primary human

  设计并合成了一系列在C2上带有各种环状和脂肪族胺的1,4-萘醌新系列，以鉴定用于三阴性乳腺癌的抗增殖剂，这代表了没有靶向疗法的临床挑战。在萘醌中，2a和3a抑制MDA-MB-231细胞的增殖（EC 50与原代人乳腺细胞MCF10A相比分别为1.6和2.7μM）。此外，它们不影响外周血单个核细胞（PBMC）的生存能力，表明它们可能更安全地用于癌症治疗。最近，G蛋白偶联受体55（GPR55）的表达与三阴性乳腺癌的发展和侵袭之间已出现相关性，使其成为靶向疗法发展的有希望的靶标。基于这一证据，分子对接研究支持了与GPR55结合的假说，药理测试表明化合物3a可以发挥其抗增殖活性，起GPR55反向激动剂的作用。
• Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds
  作者：Li-Jiau Huang、Fu-Chaio Chang、Kuo-Hsiung Lee、Jih-Pyang Wang、Che-Ming Teng、Sheng-Chu Kuo

  DOI：10.1016/s0968-0896(98)80006-0

  日期：1998.12

  and 5,8-diacetoxy (11) derivatives of the lead compound 2,3-dichloro-5,8-dimethoxy-1,4-naphthoquinone (4) were synthesized, together with 6,7-dichloro-5,8dimethoxy-1,4-naphthoquinone (5), a positional isomer of 4. Antiplatelet, antiinflammatory, and antiallergic activities were evaluated, and most compounds were quite potent in all assays. Compounds 5 and 9-11 were especially active; however, 5 was

  铅化合物2,3-二氯-苯并（2-）合成了5,8-二甲氧基-1,4-萘醌（4）和6,7-二氯-5,8-二甲氧基-1,4-萘醌（5），它是4的位置异构体。抗血小板，抗炎和抗过敏对活性进行了评估，大多数化合物在所有测定中均非常有效。化合物5和9-11具有特别的活性。然而，有5个对嗜中性白细胞超氧化物的形成无效，而10个对肥大细胞脱粒无效。
• Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase
  作者：Solomon Berhe、Andrew Slupe、Choice Luster、Henry A. Charlier、Don L. Warner、Leon H. Zalkow、Edward M. Burgess、Nkechi M. Enwerem、Oladapo Bakare

  DOI：10.1016/j.bmc.2009.11.011

  日期：2010.1

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.
• Friedel–Crafts Condensations with Maleic Anhydrides. III. The Synthesis of Polyhydroxylated Naphthoquinones
  作者：Richard Huot、Paul Brassard

  DOI：10.1139/v74-132

  日期：1974.3.1

  The condensation of hydroquinone ethers with an excess of dihalomaleic anhydrides has been found to give particularly good yields of dihalonaphthazarins. The etherification of the latter and the nu...

  已发现氢醌醚与过量的二卤代马来酸酐的缩合产生特别好的二卤萘扎林产率。后者的醚化和nu...