benzyl 2-carboxy-4-(3'-hydroxypropyl)-3,5-dimethylpyrrole | 16132-26-6

• 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: benzyl 2-carboxy-4-(3'-hydroxypropyl)-3,5-dimethylpyrrole
• 英文别名: benzyl 4-(3-hydroxypropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate；4-(3-Hydroxypropyl)-3,5-dimethylpyrrol-carbonsaeure-(2)-benzylester；benzyl 4-(3-hydroxypropyl)-3,5-dimethylpyrrole-2-carboxylate；4-(3-hydroxy-propyl)-3,5-dimethyl-pyrrole-2-carboxylic acid benzyl ester
• CAS: 16132-26-6
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: FDOLOIVLGQXREZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  62.32
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-carboxy-4-(3'-hydroxypropyl)-3,5-dimethylpyrrole 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 4-(3-acetoxypropyl)-3,5-dimethylpyrrole-2-carboxylic acid
  参考文献：
  名称：

  Hiom, John; Paine III, John B.; Zapf, Udo, Canadian Journal of Chemistry, 1983, vol. 61, p. 2220 - 2224

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzyl 3,5-dimethyl-4-<2'-(ethoxycarbonyl)-ethyl>pyrrole-2-carboxylate 在 四氢呋喃 、 硼烷 作用下， 生成 benzyl 2-carboxy-4-(3'-hydroxypropyl)-3,5-dimethylpyrrole
  参考文献：
  名称：

  Selectively metalated doubly cofacial porphyrin trimers. New models for the study of photoinduced intramolecular electron transfer.

  摘要：

  DOI：

  10.1016/s0040-4039(00)87573-5

文献信息

• Synthesis of novel texaphyrins containing lanthanides and boron
  作者：Achintya K. Bandyopadhyaya、Sureshbabu Narayanasamy、Rolf F. Barth、Werner Tjarks

  DOI：10.1016/j.tetlet.2007.04.149

  日期：2007.6

  Texaphyrin macrocycles that contain gadolinium or lutetium, such as motexafin gadolinium and motexafin lutetium, are versatile anticancer therapeutics and diagnostics. Gadolinium texaphyrins substituted with carborane clusters could also find application in combined gadolinium and boron neutron capture therapy (GdB-NCT). The synthesis and characterization of novel texaphyrins containing gadolinium or lutetium

  含有g或or的得克萨斯大环化合物，例如莫达沙芬g和莫达沙芬，是多用途的抗癌治疗剂和诊断剂。用碳硼烷簇代替的草卟啉也可以在and和硼中子捕获联合疗法（GdB-NCT）中找到应用。描述和合成新型特沙弗林，其在五氮杂核中含有and或，以及与大环相反的吡咯单元结合的两个碳硼烷簇，其合成和表征。
• Fluorogenic α-Tocopherol Analogue for Monitoring the Antioxidant Status within the Inner Mitochondrial Membrane of Live Cells
  作者：Katerina Krumova、Lana E. Greene、Gonzalo Cosa

  DOI：10.1021/ja408227f

  日期：2013.11.13

  We report here the preparation of a lipophilic fluorogenic antioxidant (Mito-Boclipy-TOH) that targets the inner mitochondrial lipid membrane (IMM) and is sensitive to the presence of lipid peroxyl radicals, effective chain carriers in the lipid chain autoxidation. Mito-Bodipy-TOH enables monitoring of the antioxidant status, i.e., the antioxidant load and ability to prevent lipid chain autoxidation, within the inner mitochondrial membrane of live cells. The new probe consists of 3 segments: a receptor, a reporter, and a mitochondria-targeting element, constructed, respectively, from an alpha-tocopherol-like chromanol moiety, a BODIPY fluorophore, and a triphenylphosphonium cation (TPP). The chromanol moiety ensures reactivity akin to that of a-tocopherol, the most potent naturally occurring lipid soluble antioxidant, while the BODIPY fluorophore and TPP ensure partitioning within the inner mitochondrial membrane. Mechanistic studies conducted either in homogeneous solution or in liposomes and in the presence of free radical initiators show that the antioxidant activity of Mito-Bodipy-TOH is on par with that of a-tocopherol. Studies conducted on live fibroblast cells further show the antioxidant depletion in the presence of methyl viologen (paraquat), a known agent of oxidative stress and source of superoxide radical anion (and indirectly, a causative of lipid peroxidation) within the mitochondria matrix. We recorded a ca. 8-fold emission enhancement with Mito-Bodipy-TOH in cells stressed with methyl viologen, whereas no enhancement was observed in control studies with untreated cells. Our findings underscore the potential of the new fluorogenic antioxidant Mito-Bodipy-TOH to study the chemical link between antioxidant load, lipid peroxidation and mitochondrial physiology.
• Holmes, Robert T.; Lu, Jianming; Mwakwari, Celinah, ARKIVOC, 2010, vol. 2010, # 5, p. 5 - 16
  作者：Holmes, Robert T.、Lu, Jianming、Mwakwari, Celinah、Smith, Kevin M.

  DOI：——

  日期：——