2-chloro-3-(isopropylamino)naphthalene-1,4-dione | 15455-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-(isopropylamino)naphthalene-1,4-dione
• 英文别名: 2-chloro-3-isopropylamino-1,4-naphthoquinone；2-chloro-3-(isopropylamino)naphthoquinone；NSC91102；2-Chlor-3-isopropylamino-α-naphthochinon；3-Isopropylamino-2-chlor-1,4-naphthochinon；2-Chloro-3-(propan-2-ylamino)naphthalene-1,4-dione
• CAS: 15455-20-6
• 化学式: C₁₃H₁₂ClNO₂
• 分子量: 249.697
• InChiKey: ZOFLWMCFCUMANX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(isopropylamino)naphthalene-1,4-dione 在 硫酸 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 N-Isopropyl-N-(3-isopropylamino-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-acetamide
  参考文献：
  名称：

  抗疟疾N 1，N 3-二烷基二氧杂萘甲并咪唑类化合物：合成，生物活性和构效关系。

  摘要：

  在这里，我们报告N 1，N 3-二烷基二氧杂萘甲并咪唑类对敏感和耐药性恶性疟原虫无性形式的纳摩尔浓度。活性取决于稠合的醌-咪唑鎓实体的存在和由支架上的N1 / N3烷基残基赋予的亲脂性。还检测到杀细胞杀灭活性，大多数成员在IC50 <1μM时有活性。具有良好溶解性，有限的PAMPA渗透性和微粒体稳定性的代表性类似物在恶性疟原虫的人源化小鼠模型上显示出口服功效。

  DOI：

  10.1021/acsmedchemlett.9b00457
• 作为产物：
  描述：

  在 paraquat dichloride 、 异丙醇 作用下， 以 水 为溶剂， 生成 2-chloro-3-(isopropylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  连接的紫精醌分子中的电子转移：速率常数随链长的增加而增强

  摘要：

  We synthesized a homologous series of molecules (MVnnQ) where a methylviologen (MV) and a aminochloronaphthoquinone (Q) are linked to each other via a flexible chain. Using the electron pulse radiolysis technique, we have measured time-resolved spectra and rate constant for intra- and intermolecular electron transfer between donor and acceptor site of the MVnnQ molecules in water and in SDS micellar solution. For comparison, we also irradiated a solution containing a 1:1 mixture of methylviologen and aminochloronaphthoquinone and measured spectra and intermolecular ET reactions between the separated electron donor and acceptor molecules. The intramolecular electron transfer rate constants of all MVnnQ molecules were surprisingly low both in water and in aqueous SDS micellar suspension. The intramolecular rate constants measured in water increase with increasing number of intervening bonds, leading to the conclusion that electron transfer occurs by a through-space rather than through-bond mechanism. The intramolecular rate constants virtually lose their chain length dependence in SDS suspensions where because of an extended configuration of the micellized MVnnQ molecules through-space interaction is not favored.

  DOI：

  10.1021/j100181a036

文献信息

• ‘On water’: unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension
  作者：Vishnu K. Tandon、Hardesh K. Maurya

  DOI：10.1016/j.tetlet.2009.07.149

  日期：2009.10

  Unique nucleophilic substitution and addition reactions of 1,4-quinones in aqueous suspension with aromatic amines, primary aliphatic amines, amino acid, ester of amino acid, heterocyclic amines, hydrazine, amide, and thioethers are described in absence of catalyst against the traditional synthetic routes of these reactions in non-aqueous medium in presence of catalyst.

  在没有传统合成催化剂的催化剂的情况下，描述了水性悬浮液中1,4-醌与芳香胺，伯脂肪胺，氨基酸，氨基酸酯，杂环胺，肼，酰胺和硫醚的独特亲核取代和加成反应催化剂存在下在非水介质中进行这些反应的途径。
• A simple synthesis of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B
  作者：Vicente Castro-Castillo、Cristian Suárez-Rozas、Sebastián Simpson、Andrés Barriga-González

  DOI：10.1007/s10593-017-2092-y

  日期：2017.5

  We followed a simple, inexpensive, and efficient route to synthesize a series of 3,4-dihydrobenzo[f]quinoxalin-6(2H)-one derivatives substituted in the ring B, with the expectation that this scaffold might exhibit antineoplastic activity. 5-Chlorobenzo[f]quinoxalin-6-ylacetate and 4-benzylbenzo[f]quinoxalin-6(4H)-one were obtained for the first time.

  我们遵循一种简单，廉价且有效的途径，合成了在环B中取代的一系列3,4-二氢苯并[ f ]喹喔啉-6（2 H）-one衍生物，并期望该支架可能具有抗肿瘤活性。首次获得5-氯苯并[ f ]喹喔啉-6-乙酸盐和4-苄基苯并[ f ]喹喔啉-6（4 H）-one。
• Dioxonaphthoimidazoliums are Potent and Selective Rogue Stem Cell Clearing Agents with SOX2-Suppressing Properties
  作者：Si-Han Sherman Ho、Azhar Ali、Yi-Cheng Ng、Kuen-Kuen Millie Lam、Shu Wang、Woon-Khiong Chan、Tan-Min Chin、Mei-Lin Go

  DOI：10.1002/cmdc.201600262

  日期：2016.9.6

  non‐pharmacological methods. Dioxonapthoimidazolium YM155, a survivin suppressant, induced selective and potent cell death of undifferentiated stem cells. Herein, the structural requirements for stemotoxicity were investigated and found to be closely aligned with those essential for cytotoxicity in malignant cells. There was a critical reliance on the quinone and imidazolium moieties but a lesser dependence on

  多能干细胞在再生医学方面具有独特的定位，但只有将其致瘤倾向与其多能特性脱钩，才能实现其临床潜力。使用小分子去除残留的未分化多能细胞，否则这些细胞会转化为畸胎瘤和畸胎瘤，与非药物方法相比具有几个优势。Dioxonapthoimidazolium YM155 是一种存活素抑制剂，可诱导未分化干细胞的选择性和强效细胞死亡。在此，对干细胞毒性的结构要求进行了研究，发现其与恶性细胞中细胞毒性所必需的结构要求密切相关。对醌和咪唑鎓部分的依赖性很大，但对环取代基的依赖性较小，主要用于微调活动。鉴定出几种有效的类似物，如 YM155，抑制干细胞中的 survivin 并降低 SOX2。SOX2 的减少会导致多能因子的不平衡，这可能会促使细胞分化，从而降低异常畸胎瘤形成的风险。由于 NF-κB p50 亚基的磷酸化也被抑制，磷酸化-p50、SOX2 和 survivin 之间的串扰可能暗示 NF-κB 信号
• Antiviral Compounds and Methods of Use Thereof
  申请人：Guenther Richard H.

  公开号：US20130071353A1

  公开（公告）日：2013-03-21

  Inhibitors of retroviral propagation, methods of treatment and prevention of retroviral infections using the inhibitors, and pharmaceutical compositions including the inhibitors, are disclosed.

  本文披露了逆转录病毒传播的抑制剂、使用这些抑制剂进行逆转录病毒感染的治疗和预防方法，以及包括这些抑制剂的制药组合物。
• Antiviral compounds and methods of use thereof
  申请人：Trana Discovery, Inc.

  公开号：US10098887B2

  公开（公告）日：2018-10-16

  Inhibitors of retroviral propagation, methods of treatment and prevention of retroviral infections using the inhibitors, and pharmaceutical compositions including the inhibitors, are disclosed.

  本研究公开了逆转录病毒传播抑制剂、使用这些抑制剂治疗和预防逆转录病毒感染的方法以及包括这些抑制剂的药物组合物。