2-二甲氨基-3-氯-1,4-萘并醌 | 5350-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-二甲氨基-3-氯-1,4-萘并醌
• 英文名称: 2-chloro-3-dimethylamino-1,4-naphthoquinone
• 英文别名: 2-dimethylamino-3-chloro-1,4-naphthoquinone；2-Chlor-3-dimethylamino-1,4-naphthochinon；2-chloro-3-(dimethylamino)naphthoquinone；2-chloro-3-(dimethylamino)naphthalene-1,4-dione；2-Chlor-3-dimethylamino-naphthochinon-(1.4)；2-Chlor-3-trimethylamino-1,4-naphthochinon；S1384445
• CAS: 5350-26-5
• 化学式: C₁₂H₁₀ClNO₂
• mdl: MFCD00193022
• 分子量: 235.67
• InChiKey: QSLFQVQZSKRPHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-二甲氨基-3-氯-1,4-萘并醌 、 sodium methylate 以 乙腈 为溶剂， 反应 1.0h， 以65%的产率得到2-dimethylamino-3-methoxy-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis, photolysis, and redox properties of 2-dialkylamino-3-methoxy-1,4-naphthoquinones

  摘要：

  DOI：

  10.1007/bf00959587
• 作为产物：
  描述：

  2-dimethylamino-1,4-naphthoquinone 在 三甲基乙酰氯 作用下， 以 苯 为溶剂， 生成 2-二甲氨基-3-氯-1,4-萘并醌
  参考文献：
  名称：

  Litvin, B. L.; Gubrii, Z. V.; Shermolovich, Yu. G., Russian Journal of Organic Chemistry, 1999, vol. 35, # 3, p. 377 - 383

  摘要：

  DOI：

文献信息

• [EN] NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE NAPHTAQUINONE MÉTHYLTRANSFÉRASE ET LEURS UTILISATIONS
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2015172076A1

  公开（公告）日：2015-11-12

  Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.

  本文提供了化合物(I)及其药用可接受的盐、溶剂合物、水合物、多型体、共晶体、互变异构体、立体异构体和其前药。还提供了涉及创新化合物用于治疗增殖性疾病（例如，癌症（例如，白血病、乳腺癌、黑色素瘤、转移性癌症）和与不当的SET8活性相关的疾病）的药物组合物和方法。还提供了用于抑制SET8的方法和用于标记SET8的方法。
• New selenenylation method. Synthesis of setenonaphthoquinones and selenoquinolinequinones mediated by phenyl selenide ion
  作者：Makoto Sakakibara、Yoshihiko Watanabe、Takeshi Toru、Yoshio Ueno

  DOI：10.1039/p19910001231

  日期：——

  aqueous NaOH was found to be a good method for the generation of phenyl selenide ion. A variety of 2-halogeno-1,4-naphthoquinones and halogenoquinolinequinones were efficiently converted into the corresponding seleno compounds. Selenenylation of 2,3-dichloro-1,4-naphthoquinone gave 2,3-bis(phenylseleno)-1,4-naphthoquinone. The reaction of 2-bromo-1,4-napthoquinone afforded 2,3-bis(phenylseleno)naphthoquinone

  发现用NaOH水溶液处理二苯基二硒化物和三丁基膦是产生苯基硒化物离子的良好方法。各种2-卤代-1,4-萘醌和卤代喹啉醌被有效地转化为相应的硒代化合物。2，3-二氯-1，4-萘醌的硒烯基化得到2，3-双（苯基硒代）-1，4-萘醌。除了作为主要产物的2-（苯基硒代）萘醌外，2-溴-1,4-萘醌的反应以明显的产率得到了2,3-双（苯基硒代）萘醌。当反应在完全无氧的条件下进行时，二硒代化合物的形成减至最少。讨论了该亚硒基化的反应机理。
• 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。
• Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber’s Hereditary Optic Neuropathy (LHON)
  作者：Carmine Varricchio、Kathy Beirne、Pascale Aeschlimann、Charles Heard、Malgorzata Rozanowska、Marcela Votruba、Andrea Brancale

  DOI：10.1021/acs.jmedchem.0c00942

  日期：2020.11.25

  Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5'-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.