Benzoic acid 8-bromo-octyl ester | 859723-88-9

• 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: Benzoic acid 8-bromo-octyl ester
• 英文别名: 8-Bromooctyl benzoate；8-bromooctyl benzoate
• CAS: 859723-88-9
• 化学式: C₁₅H₂₁BrO₂
• 分子量: 313.235
• InChiKey: HFHLXMRZODEIDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  Benzoic acid 8-bromo-octyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 Benzoic acid 8-iodo-octyl ester
  参考文献：
  名称：

  Amphiphilic pyridinium salts block TNFα/NFκB signaling and constitutive hypersecretion of interleukin-8 (IL-8) from cystic fibrosis lung epithelial cells

  摘要：

  Cystic fibrosis (CF) is a common, lethal genetic disease, which is due to mutations in the CFTR gene. The CF lung expresses a profoundly proinflammatory phenotype, due to constitutive hypersecretion of IL-8 from epithelial cells lining the airways. In a systematic search for candidate drugs that might be used therapeutically to suppress IL-8 secretion from these cells, we have identified a potent and efficacious series of amphiphilic pyridinium salts. The most potent of these salts is MRS2481, an (R)-1-phenylpropionic acid ester, with an IC50 of ca. 1 mu M. We have synthesized 21 analogues of MRS2481, which have proven sufficient to develop a preliminary structure-activity relationship (SAR). For optimal activity, we have found that the ester must be connected to the pyridinium derivative by an eight-carbon chain. An optical isomer of the lead compound, containing an (S)-1-phenylpropionic acid ester, has been found to be a much less active. The mechanism of action of MRS2481 appears to involve inhibition of signaling of the NF kappa B and AP- I transcription factors to the IL-8 promoter. MRS2481 is a potent inhibitor of TNF alpha-induced phosphorylation and proteosomal destruction Of I kappa B alpha. Inasmuch as I kappa B alpha is the principal inhibitor of the NF kappa B signaling pathway, preservation of intact I kappa B alpha would serve to keep the IL-8 promoter silent. We also find that MRS2481 blocks TNF alpha-activated phosphorylation of JNK, the c-JUN kinase. The IL-8 promoter is also activated by an AP- I site, which requires a phospho-c-JUN/c-FOS dimer for activity. We therefore interpret these data to suggest that the mechanism of MRS2481 action is to inhibit both NF kappa B and AP-1 signaling on the IL-8 promoter. Given the medicinally promising properties of water-solubility, potency in the low mu M concentration range, and high efficacy, we anticipate that MRS2481, or a further optimized derivative, may find an important place in the armamentarium of pharmaceutical strategies yet to be arrayed against the inflammatory phenotype of the CF lung. Published by Elsevier Inc.

  DOI：

  10.1016/j.bcp.2005.05.002
• 作为产物：
  描述：

  1,8-二溴辛烷 、 苯甲酸 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 Benzoic acid 8-bromo-octyl ester
  参考文献：
  名称：

  分子离子渔夫作为高活性和异常选择性的 K+ 转运蛋白

  摘要：

  我们在此报告了一种独特的离子捕捞机制，作为传统载体或通道机制的替代方案，用于介导高效和异常选择性的跨膜 K+ 通量。分子框架是钓鱼机制的基础，包括钓鱼竿、钓鱼线和鱼饵/鱼钩，简单但可模块化修改。此功能可以快速构建一系列具有截然不同的离子传输模式的分子离子捕鱼器。虽然通常通过使用 18-crown-6 作为鱼饵/钩子来实现更有效的离子传输，但离子传输选择性 (K+/Na+) 关键取决于钓鱼线的长度，最具选择性的 MF6-C14 表现出异常高的选择性 (K+/Na+ = 18) 和高活性（EC50 = 1.1 mol % 相对于脂质）。

  DOI：

  10.1021/jacs.9b04096

文献信息

• Rh(<scp>iii</scp>)-Catalyzed mild straightforward synthesis of quinoline-braced cyclophane macrocycles <i>via</i> migratory insertion
  作者：Bidhan Ghosh、Satabdi Bera、Pintu Ghosh、Rajarshi Samanta

  DOI：10.1039/d1cc04418d

  日期：——

  An efficient Rh(III)-catalyzed straightforward strategy is developed for the synthesis of quinoline braced cyclophane macrocycles via methyl (sp3) C–H functionalization. The method is mild, simple and regioselective with various ring sizes and has good functional group tolerance. The method proceeds via C8-methyl metalation, metal–carbene formation and a subsequent migratory insertion. High dilution

  开发了一种高效的 Rh( III ) 催化的直接策略，用于通过甲基 (sp 3 ) C-H 官能化合成喹啉支撑的环芳大环。该方法温和、简单且具有区域选择性，具有多种环尺寸，并具有良好的官能团耐受性。该方法通过C8-甲基金属化、金属-卡宾形成和随后的迁移插入进行。这种大环化不需要高度稀释，唯一的副产品是氮。初步调查表明，C-H 金属化步骤是决定速率的步骤。
• CYCLOPHOSPHAZENE COMPOUND, LUBRICANT COMPRISING SAME, AND MAGNETIC DISK
  申请人：MORESCO Corporation

  公开号：EP2565198A1

  公开（公告）日：2013-03-06

  A cyclophosphazene compound of the formula (I), and lubricants and magnetic disks using the compound wherein n is 2, 3 or 4, m is an integer of 1 to 12, R is C1-4 fluoroalkyl and Rf is -CF2O(CF2CF2O)x(CF2O)yCF2- or -CF2CF2O(CF2CF2CF2O)zCF2CF2- in which x, y and z are each 0 or a positive real number to give a number average molecular weight of 500 to 4000 to a fluoropolyether of the formula HOCH2-Rf-CH2OH including said Rf, the fluoropolyether having a molecular weight distribution (PD) of 1.0 to 1.5.

  式 (I) 的环磷氮化合物，以及使用该化合物的润滑剂和磁盘 其中 n 是 2、3 或 4，m 是 1 至 12 的整数，R 是 C1-4 氟烷基，Rf 是 -CF2O(CF2CF2O)x(CF2O)yCF2- 或 -CF2CF2O(CF2CF2CF2O)zCF2CF2- 其中 x、y 和 z 各为 0 或正实数，以使包括所述 Rf 的式 HOCH2-Rf-CH2OH 的含氟聚醚的数均分子量为 500 至 4000，该含氟聚醚的分子量分布 (PD) 为 1.0 至 1.5。
• US8936859B2
  申请人：——

  公开号：US8936859B2

  公开（公告）日：2015-01-20
• Molecular Ion Fishers as Highly Active and Exceptionally Selective K⁺ Transporters
  作者：Ruijuan Ye、Changliang Ren、Jie Shen、Ning Li、Feng Chen、Arundhati Roy、Huaqiang Zeng

  DOI：10.1021/jacs.9b04096

  日期：2019.6.26

  ion-fishing mechanism as an alternative to conventional carrier or channel mechanisms for mediating highly efficient and exceptionally selective transmembrane K+ flux. The molecular framework, underlying the fishing mechanism and comprising a fishing rod, a fishing line and a fishing bait/hook, is simple yet modularly modifiable. This feature enables rapid construction of a series of molecular ion fishers

  我们在此报告了一种独特的离子捕捞机制，作为传统载体或通道机制的替代方案，用于介导高效和异常选择性的跨膜 K+ 通量。分子框架是钓鱼机制的基础，包括钓鱼竿、钓鱼线和鱼饵/鱼钩，简单但可模块化修改。此功能可以快速构建一系列具有截然不同的离子传输模式的分子离子捕鱼器。虽然通常通过使用 18-crown-6 作为鱼饵/钩子来实现更有效的离子传输，但离子传输选择性 (K+/Na+) 关键取决于钓鱼线的长度，最具选择性的 MF6-C14 表现出异常高的选择性 (K+/Na+ = 18) 和高活性（EC50 = 1.1 mol % 相对于脂质）。
• Amphiphilic pyridinium salts block TNFα/NFκB signaling and constitutive hypersecretion of interleukin-8 (IL-8) from cystic fibrosis lung epithelial cells
  作者：Susanna Tchilibon、Jian Zhang、QingFeng Yang、Ofer Eidelman、Haksung Kim、Hung Caohuy、Kenneth A. Jacobson、Bette S. Pollard、Harvey B. Pollard

  DOI：10.1016/j.bcp.2005.05.002

  日期：2005.8

  Cystic fibrosis (CF) is a common, lethal genetic disease, which is due to mutations in the CFTR gene. The CF lung expresses a profoundly proinflammatory phenotype, due to constitutive hypersecretion of IL-8 from epithelial cells lining the airways. In a systematic search for candidate drugs that might be used therapeutically to suppress IL-8 secretion from these cells, we have identified a potent and efficacious series of amphiphilic pyridinium salts. The most potent of these salts is MRS2481, an (R)-1-phenylpropionic acid ester, with an IC50 of ca. 1 mu M. We have synthesized 21 analogues of MRS2481, which have proven sufficient to develop a preliminary structure-activity relationship (SAR). For optimal activity, we have found that the ester must be connected to the pyridinium derivative by an eight-carbon chain. An optical isomer of the lead compound, containing an (S)-1-phenylpropionic acid ester, has been found to be a much less active. The mechanism of action of MRS2481 appears to involve inhibition of signaling of the NF kappa B and AP- I transcription factors to the IL-8 promoter. MRS2481 is a potent inhibitor of TNF alpha-induced phosphorylation and proteosomal destruction Of I kappa B alpha. Inasmuch as I kappa B alpha is the principal inhibitor of the NF kappa B signaling pathway, preservation of intact I kappa B alpha would serve to keep the IL-8 promoter silent. We also find that MRS2481 blocks TNF alpha-activated phosphorylation of JNK, the c-JUN kinase. The IL-8 promoter is also activated by an AP- I site, which requires a phospho-c-JUN/c-FOS dimer for activity. We therefore interpret these data to suggest that the mechanism of MRS2481 action is to inhibit both NF kappa B and AP-1 signaling on the IL-8 promoter. Given the medicinally promising properties of water-solubility, potency in the low mu M concentration range, and high efficacy, we anticipate that MRS2481, or a further optimized derivative, may find an important place in the armamentarium of pharmaceutical strategies yet to be arrayed against the inflammatory phenotype of the CF lung. Published by Elsevier Inc.