4,4'-(5-bromopent-1-ene-1,1-diyl)bis(methoxybenzene) | 1609954-54-2

• 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: 4,4'-(5-bromopent-1-ene-1,1-diyl)bis(methoxybenzene)
• 英文别名: 1-[5-bromo-1-(4-methoxyphenyl)pent-1-enyl]-4-methoxybenzene
• CAS: 1609954-54-2
• 化学式: C₁₉H₂₁BrO₂
• 分子量: 361.279
• InChiKey: DURKXMIUHDNEBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-(5-bromopent-1-ene-1,1-diyl)bis(methoxybenzene) 在 Oxone 、 Shi's ketone 、 Na2B4O7*10H2O 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (S)-(1-benzylpyrrolidin-2-yl)bis(4-methoxyphenyl)methanol
  参考文献：
  名称：

  Concise Synthesis of Chiral N-Benzyl-α,α-Diarylprolinols through Shi Asymmetric Epoxidation

  摘要：

  A concise and practical synthesis of chiral N-benzyl-alpha,alpha-diaryl-2-prolinols was developed through Shi asymmetric epoxidation, followed by double nucleophilic substitution of bromo-containing olefins. A series of enantioenriched N-benzyl-alpha,alpha-diaryl-2-prolinols were obtained with excellent enantioselectivities (96% ee) in moderate to good yields (40-76% yield). For the first time, enantiopure N-benzyl-alpha,alpha-diphenyl-2-prolinol was obtained from bromo-containing olefin using this methodology.

  DOI：

  10.1055/s-0033-1340825
• 作为产物：
  描述：

  5-bromo-1,1-bis(4-methoxyphenyl)pentan-1-ol 在 盐酸 作用下， 以 乙醇 为溶剂， 以9.4 g的产率得到4,4'-(5-bromopent-1-ene-1,1-diyl)bis(methoxybenzene)
  参考文献：
  名称：

  Concise Synthesis of Chiral N-Benzyl-α,α-Diarylprolinols through Shi Asymmetric Epoxidation

  摘要：

  A concise and practical synthesis of chiral N-benzyl-alpha,alpha-diaryl-2-prolinols was developed through Shi asymmetric epoxidation, followed by double nucleophilic substitution of bromo-containing olefins. A series of enantioenriched N-benzyl-alpha,alpha-diaryl-2-prolinols were obtained with excellent enantioselectivities (96% ee) in moderate to good yields (40-76% yield). For the first time, enantiopure N-benzyl-alpha,alpha-diphenyl-2-prolinol was obtained from bromo-containing olefin using this methodology.

  DOI：

  10.1055/s-0033-1340825

文献信息

• Design, synthesis and structure-activity relationship study of novel urea compounds as FGFR1 inhibitors to treat metastatic triple-negative breast cancer
  作者：Md Ashraf-Uz-Zaman、Sadisna Shahi、Racheal Akwii、Md Sanaullah Sajib、Mohammad Jodeiri Farshbaf、Raja Reddy Kallem、William Putnam、Wei Wang、Ruiwen Zhang、Karina Alvina、Paul C. Trippier、Constantinos M. Mikelis、Nadezhda A. German

  DOI：10.1016/j.ejmech.2020.112866

  日期：2021.1

  Triple-negative breast cancer (TNBC) is an aggressive type of cancer characterized by higher metastatic and reoccurrence rates, where approximately one-third of TNBC patients suffer from the metastasis in the brain. At the same time, TNBC shows good responses to chemotherapy, a feature that fuels the search for novel compounds with therapeutic potential in this area. Recently, we have identified novel

  三阴性乳腺癌 (TNBC) 是一种侵袭性癌症，其特点是转移率和复发率较高，其中大约三分之一的 TNBC 患者患有脑转移。与此同时，TNBC 对化疗表现出良好的反应，这一特征推动了在该领域寻找具有治疗潜力的新型化合物。最近，我们已经鉴定出对选定细胞系具有细胞毒性并能够在体内穿过血脑屏障的新型尿素基化合物. 我们合成并分析了一个包含 40 多种化合物的库，以阐明导致所观察到的活性的关键特征。我们还将 FGFR1 确定为受这些化合物存在影响的分子靶标，使用计算机模型证实了我们的数据。总的来说，我们设想这些化合物可以进一步开发用于潜在的转移性乳腺癌治疗。
• Analogs of penfluridol as chemotherapeutic agents with reduced central nervous system activity
  作者：Md Ashraf-Uz-Zaman、Md Sanaullah Sajib、Luca Cucullo、Constantinos M. Mikelis、Nadezhda A. German

  DOI：10.1016/j.bmcl.2018.10.036

  日期：2018.12

  as a chemotherapeutic agent. In vivo experiments have confirmed the cytotoxic activity of penfluridol in triple-negative breast cancer model, lung cancer model, and further studies have been proposed to assess its anticancer activity and viability for the treatment of glioblastomas. However, penfluridol anticancer activity was observed at a dosage significantly higher than that administered in antipsychotic

  最近的几份报告强调了使用众所周知的抗精神病药物五氟利多作为化疗药物的可行性。体内实验已经证实了五氟利多在三阴性乳腺癌模型、肺癌模型中的细胞毒活性，并且已经提出进一步的研究来评估其抗癌活性和治疗胶质母细胞瘤的可行性。然而，在剂量显着高于抗精神病药物治疗的剂量下观察到五氟利多的抗癌活性，因此引发了对接受强化药物治疗的患者可能出现中枢神经系统副作用的担忧。在这项研究中，我们与一组类似物并排评估了五氟利多的潜在 CNS 毒性。