1-Bromcyclopentyl-p-methoxyphenylketon | 6728-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Bromcyclopentyl-p-methoxyphenylketon
• 英文别名: (1-Bromocyclopentyl)-(4-methoxyphenyl)methanone；(1-bromocyclopentyl)-(4-methoxyphenyl)methanone
• CAS: 6728-52-5
• 化学式: C₁₃H₁₅BrO₂
• 分子量: 283.165
• InChiKey: HEYBIWKOXVDZNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  1-Bromcyclopentyl-p-methoxyphenylketon 以 萘烷 为溶剂， 生成 2-Methylamino-2-(p-methoxyphenyl)-cyclohexanon
  参考文献：
  名称：

  Discovery of novel ketamine‐inspired derivatives as a protective agent against renal ischemic/reperfusion injury in Wistar rats

  摘要：

  AbstractRenal ischemia‐reperfusion (I/R) injury is a limiting factor for the success of renal grafts and is deemed greatly responsible for the mortality. A novel series of ketamine‐inspired compounds was synthesized and subjected to NF‐ĸB transcriptional inhibitory activity in LPS‐stimulated RAW264.7 cells, where entire set of compounds showed mild‐to‐moderate significant NF‐ĸB transcriptional inhibitory activity (IC50 6.53–67.52 µM). Compound 6d showed highest inhibitory activity among the tested series (IC50 2.62 µM) and found more potent as compared to ketamine as standard. The effect of compound 6d was further quantified in I/R injury in Wistar rats, where it dose‐dependently improves kidney function of rats with significant amelioration of kidney injury as suggested by histopathologic examination of renal tissues. It further showed reduction in the generation of pro‐inflammatory cytokines and improves the antioxidant status of experimental rats. Compound 6d inhibited apoptosis and increases the expression of Bcl2 and decreases Bax, and cleaved caspase‐3 level. It further reduces TLR‐4 and NF‐κB expression in renal cells of rats, with increases in IκB‐α level in Western blot analysis as compared to I/R group. In summary, our current study showed the development of a novel class of ketamine‐inspired derivatives against renal ischemia/reperfusion injury.

  DOI：

  10.1111/cbdd.14011
• 作为产物：
  描述：

  环戊基4-甲氧基苯基甲酮 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-Bromcyclopentyl-p-methoxyphenylketon
  参考文献：
  名称：

  用于构建第四纪立体中心的催化对映选择性频哪醇和 Meinwald 重排

  摘要：

  对映选择性频哪醇重排的发展极具挑战性，因为碳鎓中间体可能参与其中，这使得催化剂和底物之间的立体化学通讯难以实现。在此，我们报告了手性 N-三氟甲基磷酰胺催化的 1,2-叔二醇的对映选择性频哪醇重排和机械相关的四取代环氧化物的 Meinwald 重排，用于合成对映体富集的 2-炔基-2-芳基环己酮和 2,2-环己酮二芳基分别。还记录了以催化对映选择性频哪醇重排为关键战略步骤的 (+)-膜的全合成。

  DOI：

  10.1021/jacs.9b04551

文献信息

• Catalytic Enantioselective Pinacol and Meinwald Rearrangements for the Construction of Quaternary Stereocenters
  作者：Hua Wu、Qian Wang、Jieping Zhu

  DOI：10.1021/jacs.9b04551

  日期：2019.7.24

  enantioselective pinacol rearrangement is ex-tremely challenging due to the likelihood involvement of the carbeni-um intermediate that renders the stereochemical communication between catalyst and substrate difficult to achieve. Herein, we report chiral N-triflyl phosphoramide-catalyzed enantioselective pinacol rearrangement of 1,2-tertiary diols and mechanistically related Meinwald rearrangement of tetrasubstituted

  对映选择性频哪醇重排的发展极具挑战性，因为碳鎓中间体可能参与其中，这使得催化剂和底物之间的立体化学通讯难以实现。在此，我们报告了手性 N-三氟甲基磷酰胺催化的 1,2-叔二醇的对映选择性频哪醇重排和机械相关的四取代环氧化物的 Meinwald 重排，用于合成对映体富集的 2-炔基-2-芳基环己酮和 2,2-环己酮二芳基分别。还记录了以催化对映选择性频哪醇重排为关键战略步骤的 (+)-膜的全合成。
• Synthesis and Study the Analgesic Effects of New Analogues of Ketamine on Female Wistar Rats
  作者：Abbas Ahmadi、Mohsen Khalili、Ramin Hajikhani、Horiesadat Hosseini、Nasrin Afshin、Babak Nahri-Niknafs

  DOI：10.2174/157340612800493683

  日期：2012.4.26

  CI-581, Ketalar, I), a potent derivative of Phencyclidine (1-[1-phenylcyclohexyl] piperidine, CAS 956-90-1, PCP, II), and many of its analogues have shown anesthetic and analgesic effects. In this research, new derivatives of I, (2-[p-methoxybenzylamino]-2-[p-methoxyphenyl] cyclohexanone, ket-OCH3, III), (2-[p-methylbenzylamino]-2-[p-methoxyphenyl] cyclohexanone, ket-CH3, IV) and their intermediates (V-VIIII)

  氯胺酮（2-邻氯苯基-2-甲基氨基环己酮，CAS 1867-66-9，CI-581，Ketalar，I），苯环利定（1- [1-苯基环己基]哌啶，CAS 956-90-1， PCP，II）及其许多类似物已显示出麻醉和镇痛作用。在这项研究中，I，（2- [对甲氧基苄氨基] -2- [对甲氧基苯基]环己酮，ket-OCH3，III），（2- [对甲基苄氨基] -2- [对甲氧基苯基]合成了环己酮，ket-CH3，IV）及其中间体（V-VIIII），并使用尾部浸入（作为急性热痛的模型）和福尔马林（作为模型）对大鼠的III和IV的急性和慢性疼痛进行了评估。急性和慢性化学痛）测试。将结果与氯胺酮和对照组（盐水）进行比较。结果表明，在尾巴浸入和福尔马林测试中，
• Discovery of novel ketamine‐inspired derivatives as a protective agent against renal ischemic/reperfusion injury in Wistar rats
  作者：Li Zhu、Yin Zhang

  DOI：10.1111/cbdd.14011

  日期：2022.7

  AbstractRenal ischemia‐reperfusion (I/R) injury is a limiting factor for the success of renal grafts and is deemed greatly responsible for the mortality. A novel series of ketamine‐inspired compounds was synthesized and subjected to NF‐ĸB transcriptional inhibitory activity in LPS‐stimulated RAW264.7 cells, where entire set of compounds showed mild‐to‐moderate significant NF‐ĸB transcriptional inhibitory activity (IC50 6.53–67.52 µM). Compound 6d showed highest inhibitory activity among the tested series (IC50 2.62 µM) and found more potent as compared to ketamine as standard. The effect of compound 6d was further quantified in I/R injury in Wistar rats, where it dose‐dependently improves kidney function of rats with significant amelioration of kidney injury as suggested by histopathologic examination of renal tissues. It further showed reduction in the generation of pro‐inflammatory cytokines and improves the antioxidant status of experimental rats. Compound 6d inhibited apoptosis and increases the expression of Bcl2 and decreases Bax, and cleaved caspase‐3 level. It further reduces TLR‐4 and NF‐κB expression in renal cells of rats, with increases in IκB‐α level in Western blot analysis as compared to I/R group. In summary, our current study showed the development of a novel class of ketamine‐inspired derivatives against renal ischemia/reperfusion injury.