4-methoxybenzenecarboselenoic acid | 105223-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-methoxybenzenecarboselenoic acid
• 英文别名: p-Methoxy-selenobenzoesaeure
• CAS: 105223-29-8
• 化学式: C₈H₈O₂Se
• 分子量: 215.11
• InChiKey: WUGYMSWEFAXFSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-methoxybenzenecarboselenoic acid 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 2.33h， 生成 Se-methyl 4-methoxybenzenecarboselenate
  参考文献：
  名称：

  酰基氨基甲酰基硒化物和相关硫同系物：合成和 X 射线结构分析

  摘要：

  发现硒羧酸 [RC(=O)SeH] 容易与芳基、酰基和芳烃磺酰基异氰酸酯反应生成相应的酰基氨基甲酰基硒化物 3 [RC(=O)SeC(=O)NHR', R' = 芳基， C6H5CO 和 4-MeC6H4SO2] 收率良好。它们的互变异构体 [RC(=O)SeC(=NR')OH] 也被 1H、13C 和 77Se NMR 光谱检测到。3 [R = 2,6-(MeO)2C6H3, R' = 4-MeC6H4] 的结构通过 X 射线晶体学表征，表明该分子通过羰基氧和 NH 之间的分子内氢键稳定氢形成平面六元环，并通过邻甲氧基氧与羰基氧或硒原子的非键相互作用。4-甲氧基苯甲酰基和 4-甲氧基硫代苯甲酰基 N-（4-甲基苯基）氨基甲酰基硫化物（4 和 5）通过 X 射线晶体学显示同样具有由羰基氧或硫羰基硫之间的氢键形成的平面分子内六元环和 NH 氢原子。互变异构体 [RC(=E)SC(=NR')OH;

  DOI：

  10.1002/hc.1040
• 作为产物：
  描述：

  bis(4-methoxybenzoic) selenoanhydride 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 4-methoxybenzenecarboselenoic acid
  参考文献：
  名称：

  THE SYNTHESES OF POTASSIUM SELENOCARBOXYLATES AND THEIR DERIVATIVES

  摘要：

  在甲醇钾与二酰基硒反应下，成功制备了高产率的钾硒羧酸盐。这些化合物在氮气环境下相当稳定，并且可作为制备硒羧酸衍生物的起始材料，包括甲基硒苯甲酸酯、α-（硒苯甲酰基）乙酰苯、苯基对氯苯甲酰二硒化物、O-三甲基硅基硒苯甲酸酯、双（硒硬脂酰基）甲烷，以及二苯甲酰二硒化物。

  DOI：

  10.1246/cl.1976.203

文献信息

• Novel Methylselenoesters as Antiproliferative Agents
  作者：Nuria Díaz-Argelich、Ignacio Encío、Daniel Plano、Aristi P. Fernandes、Juan Antonio Palop、Carmen Sanmartín

  DOI：10.3390/molecules22081288

  日期：——

  Selenium (Se) compounds are potential therapeutic agents in cancer. Importantly, the biological effects of Se compounds are exerted by their metabolites, with methylselenol (CH3SeH) being one of the key executors. In this study, we developed a new series of methylselenoesters with different scaffolds aiming to modulate the release of CH3SeH. The fifteen compounds follow Lipinski’s Rule of Five and with exception of compounds 1 and 14, present better drug-likeness values than the positive control methylseleninic acid. The compounds were evaluated to determine their radical scavenging activity. Compound 11 reduced both DPPH and ABTS radicals. The cytotoxicity of the compounds was evaluated in a panel of five cancer cell lines (prostate, colon and lung carcinoma, mammary adenocarcinoma and chronic myelogenous leukemia) and two non-malignant (lung and mammary epithelial) cell lines. Ten compounds had GI50 values below 10 μM at 72 h in four cancer cell lines. Compounds 5 and 15 were chosen for further characterization of their mechanism of action in the mammary adenocarcinoma cell line due to their similarity with methylseleninic acid. Both compounds induced G2/M arrest whereas cell death was partially executed by caspases. The reduction and metabolism were also investigated, and both compounds were shown to be substrates for redox active enzyme thioredoxin reductase.

  硒（Se）化合物在癌症治疗中具有潜在的治疗作用。重要的是，硒化合物的生物效应是通过其代谢产物发挥的，其中甲基硒醇（CH3SeH）是一个关键的执行者。在本研究中，我们开发了一系列具有不同骨架的甲基硒酯，旨在调节CH3SeH的释放。这十五种化合物遵循Lipinski的五规则，并且除了化合物1和14外，其药物相似性值均优于阳性对照甲基硒酸。对这些化合物进行了自由基清除活性评估，其中化合物11能减少DPPH和ABTS自由基。在五种癌细胞系（前列腺、结肠和肺癌，乳腺腺癌和慢性髓性白血病）和两种非恶性细胞系（肺和乳腺上皮）中评估了这些化合物的细胞毒性。十种化合物在72小时内在四种癌细胞系中GI50值低于10 μM。由于与甲基硒酸的相似性，化合物5和15被选为进一步在乳腺腺癌细胞系中进行作用机制表征。这两种化合物均诱导G2/M期阻滞，而细胞死亡部分通过caspase介导。还研究了它们的还原和代谢，这两种化合物都被证明是还原型酶硫氧还蛋白还原酶的底物。
• Group 13 metal carbochalcogenoato complexes: Synthesis, X-ray structure analysis, and reactions
  作者：Norio Nakata、Shinzi Kato、Osamu Niyomura、Masahiro Ebihara

  DOI：10.1002/hc.21445

  日期：2018.12

  AbstractA series of alkali metal tetrakis(carbochalcogenoato)‐gallates and ‐indates M[M′(EOCR)4](solv.) (M = alkali metal; M′ = Ga, In; E = S, Se) and tris(carbodithioato)aluminum, ‐gallates and ‐indates M′ (SSCR)3 (M′ = Al, Ga, In) were prepared by the reactions of alkali metal carbochalcogenate with metal trihalogenides (M′X3; M′ = Al, Ga, In; X = Cl, Br) and by those of piperidinium carbodithioates or carbodithioic and carboselenoic acids with M′X3, respectively. An X‐ray molecular structure analysis revealed that they have an acetone molecule as a crystal solvent. The reactions of the potassium complexes K[M′ (EOCR)4](H2O) (E = S, Se) with methanol and primary and secondary amines gave the corresponding methyl ester and amides in good yields, while the reactions with iodomethane and iodine gave S‐ and Se‐methyl chalcogenoesters RCOEMe (E = S, Se) in good yields. Similar reactions of the tris(carbodithioato)gallates and ‐indates led to the corresponding O‐methyl thioesters, thioamides, and S‐methyl dithioesters in moderate to good yields. Oxidation of the tetrakis‐ and tris‐derivatives with iodine afforded the corresponding diacyl dichalcogenides (RCOE)2 (E = S, Se) and di(carbothioyl) disulfides in quantitative yields. These reactions appeared to occur on the carbonyl or selenium atom of the tetrakis compounds and on the sulfide sulfur or thiocarbonyl carbon atom of the tris‐compounds, respectively. A possible mechanism for these I2‐oxidation reactions is discussed.