2-methyl-3-(phenylselanyl)naphthalene-1,4-dione | 134717-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-3-(phenylselanyl)naphthalene-1,4-dione
• 英文别名: 2-Methyl-3-phenylselanylnaphthalene-1,4-dione
• CAS: 134717-17-2
• 化学式: C₁₇H₁₂O₂Se
• 分子量: 327.241
• InChiKey: LDPNGFAGJZEFJE-UHFFFAOYSA-N

物化性质

• 沸点：
  441.1±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  甲萘醌 、 二苯基二硒醚 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以87%的产率得到2-methyl-3-(phenylselanyl)naphthalene-1,4-dione
  参考文献：
  名称：

  室温下香豆素/（杂）芳烃的无金属区域选择性CH硫族化。

  摘要：

  提出了一种新颖，实用且无金属的室温下使用（双（三氟乙酰氧基）碘）苯（PIFA）的香豆素区域选择性硒化方法。所开发的方法适用于广泛的底物范围，并以高至优异的产率和高选择性提供了3-硒基香豆素。为这种新的转变提出了一种激进的机制。此外，在该转化中成功应用了香豆素的亚磺酰化和其他（杂）芳烃的硒化。

  DOI：

  10.1039/c9cc09001k

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。
• Exploring synthetic avenues for the effective synthesis of selenium- and tellurium-containing multifunctional redox agents
  作者：Susanne Mecklenburg、Saad Shaaban、Lalla A. Ba、Torsten Burkholz、Thomas Schneider、Britta Diesel、Alexandra K. Kiemer、Anne Röseler、Katja Becker、Jörg Reichrath、Alexandra Stark、Wolfgang Tilgen、Muhammad Abbas、Ludger A. Wessjohann、Florenz Sasse、Claus Jacob

  DOI：10.1039/b907831b

  日期：——

  Various human illnesses, including several types of cancer and infectious diseases, are related to changes in the cellular redox homeostasis. During the last decade, several approaches have been explored which employ such disturbed redox balances for the benefit of therapy. Compounds able to modulate the intracellular redox state of cells have been developed, which effectively, yet also selectively, appear to kill cancer cells and a range of pathogenic microorganisms. Among the various agents employed, certain redox catalysts have shown considerable promise since they are non-toxic on their own yet develop an effective, often selective cytotoxicity in the presence of the ‘correct’ intracellular redox partners. Aminoalkylation, amide coupling and multicomponent reactions are suitable synthetic methods to generate a vast number of such multifunctional catalysts, which are chemically diverse and, depending on their structure, exhibit various interesting biological activities.

  人类的各种疾病，包括几种癌症和传染病，都与细胞氧化还原平衡的变化有关。过去十年间，人们探索了几种方法，利用这种紊乱的氧化还原平衡来进行治疗。目前已开发出能够调节细胞内氧化还原状态的化合物，这些化合物能够有效但也有选择性地杀死癌细胞和一系列病原微生物。在所使用的各种药剂中，某些氧化还原催化剂显示出相当大的前景，因为它们本身无毒，但在 "正确的 "细胞内氧化还原伙伴存在的情况下，会产生有效的、通常是选择性的细胞毒性。氨基烷基化、酰胺偶联和多组分反应是生成大量此类多功能催化剂的合适合成方法。
• 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.