deoxynyboquinone | 96748-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: deoxynyboquinone
• 英文别名: DNQ；1,4,6-trimethyl-9H-pyrido[3,2-g]quinoline-2,5,8,10-tetrone
• CAS: 96748-86-6
• 化学式: C₁₅H₁₂N₂O₄
• 分子量: 284.271
• InChiKey: KJYPAIRTXRKKHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  deoxynyboquinone 在 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 生成
  参考文献：
  名称：

  [EN] COMPOUNDS AND ANTI-TUMOR NQO1 SUBSTRATES
  [FR] COMPOSÉS ET SUBSTRATS ANTITUMORAUX NQO1

  摘要：

  化合物的化学式（I）可以选择性地对多种不同类型的癌细胞具有致命作用。这些化合物对于管理、治疗、控制或辅助治疗疾病非常有用，其中选择性的致命作用在化疗疗法中具有益处。

  公开号：

  WO2013056073A1
• 作为产物：
  描述：

  (4,6-dichloro-5-methoxy-1,3-phenylene)bis(trimethylsilane) 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 salcomine 、 氢溴酸 、 氧气 、 potassium acetate 、 一氯化碘 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 44.41h， 生成 deoxynyboquinone
  参考文献：
  名称：

  [EN] COMPOUNDS AND ANTI-TUMOR NQO1 SUBSTRATES
  [FR] COMPOSÉS ET SUBSTRATS ANTITUMORAUX NQO1

  摘要：

  化合物的化学式（I）可以选择性地对多种不同类型的癌细胞具有致命作用。这些化合物对于管理、治疗、控制或辅助治疗疾病非常有用，其中选择性的致命作用在化疗疗法中具有益处。

  公开号：

  WO2013056073A1

文献信息

• Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated <i>Streptomyces</i>
  作者：Xiachang Wang、Sherif I. Elshahawi、Larissa V. Ponomareva、Qing Ye、Yang Liu、Gregory C. Copley、James C. Hower、Bruce E. Hatcher、Madan K. Kharel、Steven G. Van Lanen、Qing-Bai She、S. Randal Voss、Jon S. Thorson、Khaled A. Shaaban

  DOI：10.1021/acs.jnatprod.9b01015

  日期：2019.12.27

  isolation and characterization of three new nybomycins (nybomycins B-D, 1-3) and six known compounds (nybomycin, 4; deoxynyboquinone, 5; α-rubromycin, 6; β-rubromycin, 7; γ-rubromycin, 8; and [2α(1E,3E),4β]-2-(1,3-pentadienyl)-4-piperidinol, 9) from the Rock Creek (McCreary County, KY) underground coal mine acid reclamation site isolate Streptomyces sp. AD-3-6. Nybomycin D (3) and deoxynyboquinone (5) displayed

  我们报告了三种新的霉素（nybomycins BD，1-3）和六种已知化合物（nybomycin，4; deoxynyboquinone，5;α-rubromycin，6;β-rubromycin，7;γ-rubromycin，8;和6种已知化合物的分离和表征。 [2α（1E，3E），4β] -2-（1,3-戊二烯基）-4-哌啶醇，9）来自Rock Creek（McCreary County，KY）地下煤矿酸回收场，分离到Streptomyces sp.。AD-3-6。Nybomycin D（3）和Deoxynyboquinone（5）表现出中度（3）至强效（5）癌细胞系细胞毒性，并表现出弱至中度的抗Gram-（+）细菌活性，而rubromycins 6-8则几乎没有癌细胞。系细胞毒性，但具有中等至强效的抗革兰氏阳性细菌和抗真菌活性。评估3种或5种癌细胞系治疗对4E-BP1磷酸化的影响，R
• Compounds and anti-tumor NQO1 substrates
  申请人：The Board of Trustees of the University of Illinois

  公开号：US10285986B2

  公开（公告）日：2019-05-14

  Compositions comprising Formula (I) can be selectively lethal toward a variety of different cancer cell types. The compositions are useful for the management, treatment, control, or adjunct treatment of diseases, where the selective lethality is beneficial in chemotherapeutic therapy.

  由式（I）组成的组合物可对多种不同类型的癌细胞产生选择性杀伤作用。这些组合物可用于疾病的管理、治疗、控制或辅助治疗，其中选择性致死在化疗中是有益的。
• Tumor-selective combination therapy
  申请人：The Board of Regents of the University of Texas System

  公开号：US10576096B2

  公开（公告）日：2020-03-03

  The therapies described herein can be selectively lethal toward a variety of different cancer cell types and cancer conditions in a subject. The combination therapies described herein can be useful for the management, treatment, control, or adjunct treatment of diseases, where the selective legality is beneficial in chemotherapeutic therapy, particularly where the disease is accompanied by elevated levels of NQO1.

  本文所述的疗法可选择性地杀死受试者体内各种不同的癌细胞类型和癌症病症。本文所述的组合疗法可用于疾病的管理、治疗、控制或辅助治疗，其中选择性的合法性有利于化疗，特别是在疾病伴有 NQO1 水平升高的情况下。
• Chemistry and Biology of Deoxynyboquinone, a Potent Inducer of Cancer Cell Death
  作者：Joseph S. Bair、Rahul Palchaudhuri、Paul J. Hergenrother

  DOI：10.1021/ja100610m

  日期：2010.4.21

  Deoxynyboquinone (DNQ) is a potent antineoplastic agent with an unknown mechanism of action. Here we describe a facile synthetic route to this anthraquinone, and we use this material to determine the mechanism by which DNQ induces death in cancer cells. DNQ was synthesized in seven linear steps through a route employing three palladium-mediated coupling reactions. Experiments performed on cancer cells grown in hypoxia and normoxia strongly suggest that DNQ undergoes bioreduction to its semiquinone, which then is re-oxidized by molecular oxygen, forming superoxide that induces cell death. Furthermore, global transcript profiling of cells treated with DNQ shows elevation of transcripts related to oxidative stress, a result confirmed at the protein level by Western blotting. In contrast to most other antineoplastic agents that generate reactive oxygen species (ROS), DNQ potently induces death of cancer cells in culture, with IC50 values between 16 and 210 nM. In addition, unlike the experimental therapeutic elesclomol, DNQ is still able to induce cancer cell death under hypoxic conditions. This mechanistic understanding of DNQ will allow for a more comprehensive evaluation of the potential of direct ROS generation as an anticancer strategy, and DNQ itself has potential as a novel anticancer agent.
• COMPOUNDS AND ANTI-TUMOR NQO1 SUBSTRATES
  申请人：The Board of Trustees of the University of Illinois

  公开号：EP2768308B1

  公开（公告）日：2018-04-18