ethyl 4-phenyltellurenylbutyrate | 365413-54-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 4-phenyltellurenylbutyrate
• 英文别名: Ethyl 4-phenyltellanylbutanoate
• CAS: 365413-54-3
• 化学式: C₁₂H₁₆O₂Te
• 分子量: 319.858
• InChiKey: IQDHILWYAYVXKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4-phenyltellurenylbutyrate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以93%的产率得到4-phenyltellurenylbutyric acid
  参考文献：
  名称：

  Thioredoxin reductase and cancer cell growth inhibition by organotellurium compounds that could be selectively incorporated into tumor cells

  摘要：

  The thioredoxins are small ubiquitous redox proteins with the conserved redox catalytic sequence-Trp-Cys-Gly-Pro-Cys-Lys, where the Cys residues undergo reversible NADPH dependent reduction by selenocysteine containing flavoprotein thioredoxin reductases. Thioredoxin expression is increased in several human primary cancers including lung, colon, cervix, liver, pancreatic, colorectal and squamous cell cancer. The thioredoxin/thioredoxin reductase pathway therefore provides an attractive target for cancer drug development. Organotellurium steroid, lipid, amino acid, nucleic base, and polyamine inhibitors were synthesized on the basis that they might be selectively or differentially incorporated into tumor cells. Some of the newly prepared classes of tellurium-based inhibitors (lipid-like compounds 3b and 3e, amino acid derivative 5b, nucleic base derivative 8b, and polyamine derivatives 14a and 14b) inhibited TrxR/Trx and cancer cell growth in culture with IC50 values in the low micromolar range. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.021
• 作为产物：
  描述：

  4-溴丁酸乙酯 、 联苯二碲 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.33h， 以94%的产率得到ethyl 4-phenyltellurenylbutyrate
  参考文献：
  名称：

  Thioredoxin reductase and cancer cell growth inhibition by organotellurium compounds that could be selectively incorporated into tumor cells

  摘要：

  The thioredoxins are small ubiquitous redox proteins with the conserved redox catalytic sequence-Trp-Cys-Gly-Pro-Cys-Lys, where the Cys residues undergo reversible NADPH dependent reduction by selenocysteine containing flavoprotein thioredoxin reductases. Thioredoxin expression is increased in several human primary cancers including lung, colon, cervix, liver, pancreatic, colorectal and squamous cell cancer. The thioredoxin/thioredoxin reductase pathway therefore provides an attractive target for cancer drug development. Organotellurium steroid, lipid, amino acid, nucleic base, and polyamine inhibitors were synthesized on the basis that they might be selectively or differentially incorporated into tumor cells. Some of the newly prepared classes of tellurium-based inhibitors (lipid-like compounds 3b and 3e, amino acid derivative 5b, nucleic base derivative 8b, and polyamine derivatives 14a and 14b) inhibited TrxR/Trx and cancer cell growth in culture with IC50 values in the low micromolar range. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.021

文献信息

• Tin-free Radical Cyanation of Alkyl Iodides and Alkyl Phenyl Tellurides
  作者：Sunggak Kim、Hyun-Ji Song

  DOI：10.1055/s-2002-35589

  日期：——

  As a result of much faster phenyl telluride group transfer relative to the corresponding iodine atom transfer, tin-free radical cyanation of alkyl phenyl tellurides has been achieved with p-toluenesufonyl cyanide and methyl allyl sulfone in the presence of V-40 as initiator.

  由于苯基碲化物基团的转移速度比相应的碘原子转移快得多，在 V-40 作为引发剂的存在下，用对甲苯磺酰氰和甲基烯丙基砜实现了烷基苯基碲化物的无锡自由基氰化。
• Thioredoxin reductase and cancer cell growth inhibition by organotellurium compounds that could be selectively incorporated into tumor cells
  作者：Lars Engman、Nawaf Al-Maharik、Michael McNaughton、Anne Birmingham、Garth Powis

  DOI：10.1016/j.bmc.2003.08.021

  日期：2003.11

  The thioredoxins are small ubiquitous redox proteins with the conserved redox catalytic sequence-Trp-Cys-Gly-Pro-Cys-Lys, where the Cys residues undergo reversible NADPH dependent reduction by selenocysteine containing flavoprotein thioredoxin reductases. Thioredoxin expression is increased in several human primary cancers including lung, colon, cervix, liver, pancreatic, colorectal and squamous cell cancer. The thioredoxin/thioredoxin reductase pathway therefore provides an attractive target for cancer drug development. Organotellurium steroid, lipid, amino acid, nucleic base, and polyamine inhibitors were synthesized on the basis that they might be selectively or differentially incorporated into tumor cells. Some of the newly prepared classes of tellurium-based inhibitors (lipid-like compounds 3b and 3e, amino acid derivative 5b, nucleic base derivative 8b, and polyamine derivatives 14a and 14b) inhibited TrxR/Trx and cancer cell growth in culture with IC50 values in the low micromolar range. (C) 2003 Elsevier Ltd. All rights reserved.