2-(phenyltelluryl)-3-methyl-[1,4]naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(phenyltelluryl)-3-methyl-[1,4]naphthoquinone
• 英文别名: 2-(phenyltellanyl)-3-methylnaphthoquinone；2-Methyl-3-phenyltellanylnaphthalene-1,4-dione
• 化学式: C₁₇H₁₂O₂Te
• 分子量: 375.881
• InChiKey: BKVMNWGUHUWTBP-UHFFFAOYSA-N

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 在 sodium tetrahydroborate 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.33h， 生成 2-(phenyltelluryl)-3-methyl-[1,4]naphthoquinone
  参考文献：
  名称：

  Multifunctional redox catalysts as selective enhancers of oxidative stress

  摘要：

  某些癌细胞会在氧化应激（OS）条件下增殖，因此可能会被氧化还原催化剂选择性地靶向。在这些催化剂中，含有一个查尔根和一个醌氧化还原中心的化合物特别适合对氧化应激的存在做出反应。这些催化剂结合了醌和查耳酮的特殊电化学特性。它们对细胞培养中受到氧化压力的大鼠 PC12、人类 Jurkat 和人类 Daudi 细胞具有很高的选择性和效率，其作用模式很可能是催化活化现有的活性氧物种并生成新的活性氧物种。这些催化剂表现出的高效率和高选择性使它们成为开发抗癌药物的有趣材料。

  DOI：

  10.1039/b502197a

文献信息

• 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.
• Multifunctional redox catalysts as selective enhancers of oxidative stress
  作者：Fiona H. FryThese authors contributed equall、Andrea L. Holme、Niroshini M. Giles、Gregory I. Giles、Catriona Collins、Kim Holt、Sandra Pariagh、Thomas Gelbrich、Michael B. Hursthouse、Nick J. Gutowski、Claus Jacob

  DOI：10.1039/b502197a

  日期：——

  Certain cancer cells proliferate under conditions of oxidative stress (OS) and might therefore be selectively targeted by redox catalysts. Among these catalysts, compounds containing a chalcogen and a quinone redox centre are particularly well suited to respond to the presence of OS. These catalysts combine the specific electrochemical features of quinones and chalcogens. They exhibit high selectivity and efficiency against oxidatively stressed rat PC12, human Jurkat and human Daudi cells in cell culture, where their mode of action most likely involves the catalytic activation of existent and the generation of new reactive oxygen species. The high efficiency and selectivity shown by these catalysts makes them interesting for the development of anti-cancer drugs.

  某些癌细胞会在氧化应激（OS）条件下增殖，因此可能会被氧化还原催化剂选择性地靶向。在这些催化剂中，含有一个查尔根和一个醌氧化还原中心的化合物特别适合对氧化应激的存在做出反应。这些催化剂结合了醌和查耳酮的特殊电化学特性。它们对细胞培养中受到氧化压力的大鼠 PC12、人类 Jurkat 和人类 Daudi 细胞具有很高的选择性和效率，其作用模式很可能是催化活化现有的活性氧物种并生成新的活性氧物种。这些催化剂表现出的高效率和高选择性使它们成为开发抗癌药物的有趣材料。