2,3-di-(phenylseleno)-1,4-naphthoquinone | 130826-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-di-(phenylseleno)-1,4-naphthoquinone
• 英文别名: 2,3-bis(phenylseleno)-1,4-napthoquinone；2,3-Bis(phenylselanyl)naphthalene-1,4-dione
• CAS: 130826-05-0
• 化学式: C₂₂H₁₄O₂Se₂
• 分子量: 468.272
• InChiKey: HOQOKUWUFWDHEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2,3-di-(phenylseleno)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and Selective Anticancer Activity of Organochalcogen Based Redox Catalysts

  摘要：

  Many tumor cells exhibit a disturbed intracellular redox state resulting in higher levels of reactive oxygen species (ROS). As these contribute to tumor initiation and sustenance, catalytic redox agents combining significant atctivity with substrate specificity promise high activity andselectivity L. Must oxidatively stressed malignant cells. We describe here the design and synthesis of novel organochalcogen based redox sensor/effector catalysts. Their selective anticancer activity at submicromolar and low micromolar concentrations was established here in a range of tumor entities in various biological systems including cell lines, primary tumor cell cultures, and animal models. In the B-cell derived chronic lymphocytic leukemia (CLL), for instance, such compounds preferentially induce apoptosis in the cancer cells while peripheral blood mononuclear cells (PBMC) from healthy donors and the subset of normal 13-cells remain largely unaffected. In support of the concept of sensor/effector based ROS amplification, we are able to demonstrate that underlying this selective activity against CI.I. cells are pre-existing, elevated ROS levels in the leukemic cells compared to their nonmalignant counterparts. Furthermore, the catalysts act in concert with certain chemotherapeutic drugs in several carcinoma cell lines to decrease cell proliferation while showing no such interactions in normal cells. Overall, the high efficacy and selectivity of. (redox) catalytic sensor/effector compounds warrant further, extensive testing toward transfer into the clinical arena.

  DOI：

  10.1021/jm100576z

文献信息

• 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。
• C–H Diselenation and Monoselenation of Electron-Deficient Alkenes via Radical Coupling at Room Temperature
  作者：Yao Chen、Mengxia Lv、Yuxin Zhang、Yao Wu、Linkun Ying、Jielin Tang、Xiangnan Gong、Jianmin Zhou、Zengqiang Song

  DOI：10.1021/acs.joc.2c01567

  日期：2022.12.16

  A new, simple, and metal-free route for the diselenation of maleimides has been first developed employing (bis(trifluoroacetoxy)iodo)benzene (PIFA) at room temperature. The present method is compatible with different functional groups, and various diselenyl maleimides were obtained in moderate to excellent yields. Moreover, this protocol further highlights the unique practical application for the functionalization

  首先开发了一种新的、简单的、无金属的马来酰亚胺脱硒途径，该途径在室温下使用（双（三氟乙酰氧基）碘）苯 (PIFA)。本方法适用于不同的官能团，并以中等至优异的收率获得了各种二硒基马来酰亚胺。此外，该协议进一步强调了生物学相关分子和氨基酸衍生物功能化的独特实际应用。初步的机制研究表明，自由基可能参与了这种新的转变。此外，该协议还适用于通过切换其他缺电子烯烃的反应条件和硒化来实现马来酰亚胺的单硒化。
• Some Novel Quinone-Type Compounds Containing Arylseleno Groups Derived from Tetrachloro-1, 4-Benzoquinone and 2, 3-Dichloro-1, 4-Naphthoquinone
  作者：Wei-Qiang Fan、Jin Wang、Jinlong Jiang、Yong-Min Zhang

  DOI：10.1080/00397919209409254

  日期：1992.11

  Tetrachloro-1,2-benzoquinone and 2,3-dichloro-1,4-naphthoquinone react with a series of aryl and alkyl selenolate, generated either by the reaction of Grignard reagents and selenium powder or by the reduction of diselenides with NaBH4, to give 3,6-diarylseleno-2,5-dichloro-1,4-benzoquinones 3 and 2,3-diarylseleno-1,4-naphthoquinones 4 in good yields.
• Synthesis and Selective Anticancer Activity of Organochalcogen Based Redox Catalysts
  作者：Mandy Doering、Lalla A. Ba、Nils Lilienthal、Carole Nicco、Christiane Scherer、Muhammad Abbas、Abdul Ali Peer Zada、Romain Coriat、Torsten Burkholz、Ludger Wessjohann、Marc Diederich、Frederic Batteux、Marco Herling、Claus Jacob

  DOI：10.1021/jm100576z

  日期：2010.10.14

  Many tumor cells exhibit a disturbed intracellular redox state resulting in higher levels of reactive oxygen species (ROS). As these contribute to tumor initiation and sustenance, catalytic redox agents combining significant atctivity with substrate specificity promise high activity andselectivity L. Must oxidatively stressed malignant cells. We describe here the design and synthesis of novel organochalcogen based redox sensor/effector catalysts. Their selective anticancer activity at submicromolar and low micromolar concentrations was established here in a range of tumor entities in various biological systems including cell lines, primary tumor cell cultures, and animal models. In the B-cell derived chronic lymphocytic leukemia (CLL), for instance, such compounds preferentially induce apoptosis in the cancer cells while peripheral blood mononuclear cells (PBMC) from healthy donors and the subset of normal 13-cells remain largely unaffected. In support of the concept of sensor/effector based ROS amplification, we are able to demonstrate that underlying this selective activity against CI.I. cells are pre-existing, elevated ROS levels in the leukemic cells compared to their nonmalignant counterparts. Furthermore, the catalysts act in concert with certain chemotherapeutic drugs in several carcinoma cell lines to decrease cell proliferation while showing no such interactions in normal cells. Overall, the high efficacy and selectivity of. (redox) catalytic sensor/effector compounds warrant further, extensive testing toward transfer into the clinical arena.