1-Bromo-cyclopentanecarbaldehyde | 408330-29-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1-Bromo-cyclopentanecarbaldehyde
• 英文别名: 1-Bromocyclopentane-1-carbaldehyde
• CAS: 408330-29-0
• 化学式: C₆H₉BrO
• 分子量: 177.041
• InChiKey: WVHFAARGBKHLQW-UHFFFAOYSA-N

物化性质

• 沸点：
  185.5±23.0 °C(Predicted)
• 密度：
  1.637±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Bromo-cyclopentanecarbaldehyde 在 palladium on activated charcoal 甲酸 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 25.0 ℃ 、350.0 kPa 条件下， 反应 21.5h， 生成 (+)-trans-9-<6-chloro-3-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-yl>-6-methyl-6,9-diazaspiro<4.5>decane
  参考文献：
  名称：

  Enhanced D1 Affinity in a Series of Piperazine Ring Substituted 1-Piperazino-3-Arylindans with Potential Atypical Antipsychotic Activity

  摘要：

  A study of the effect of aromatic substitution on D-1 and D-2 affinity in a series of previously reported trans-1-piperazino-3-phenylindans shows similar structure-activity relationships for the two receptor sites. 6-Substituted derivatives have affinity for both receptors, and 6-chloro- or B-fluoro-substituted derivatives show preference for D-1 receptors. D-1 affinity and selectivity are significantly increased in a series of new piperazine ring substituted derivatives. Potent D-1 and D-2 antagonism in vivo are confined to derivatives with relatively small substituents in the 2-position of the piperazine ring (e.g. 2-methyl, 2,2-dimethyl, 2-spirocyclobutyl or 2-spirocyclopentyl). Consequently, the effect of aromatic substitution is examined in a series of 1-(2,2-dimethylpiperazino)-3-arylindans. All these compounds except the 4-, 5-, 7- and 4'-chlorosubstituted derivatives have potent D-1 affinity (IC50's below 10 nM) and the majority of the compounds antagonize SK&F 38393-induced circling in 6-OHDA-lesioned rats with ED(50) values about 1 mu mol/kg. In vitro all compounds show preference for D-1 receptors, but in vivo they are equally effective as D-1 and D-2 antagonists. The compounds have high affinity for 5-HT2 receptors and selected compounds show high affinity for alpha(1) adrenoceptors. Furthermore, a subgroup consisting of (-)-38, (-)-39, (-)-41, and (-)-54 does not induce catalepsy in rats. These compounds have the potential of being ''atypical'' antipsychotics and have consequently been selected for further studies. The non-receptor-blocking enantiomers are shown to be inhibitors of DA and NE uptake in accordance with previous observations in compounds unsubstituted in the piperazine ring. Two compounds, (+)-38 and (+)-40, block DA uptake with IC50 values below 10 nM. Finally, the observed structure-activity relationships are discussed in relation to previously published pharmacophore models for D-2 and 5-HT2 receptors. It is concluded that the piperazine substituents might induce a different binding mode at the dopamine receptor sites, perhaps only at the D-1 receptor site.

  DOI：

  10.1021/jm00022a004
• 作为产物：
  描述：

  环戊基溴化镁 在 溴 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 72.0h， 生成 1-Bromo-cyclopentanecarbaldehyde
  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

文献信息

• Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides
  作者：Xuan Wang、Guobin Ma、Yu Peng、Chloe E. Pitsch、Brenda J. Moll、Thu D. Ly、Xiaotai Wang、Hegui Gong

  DOI：10.1021/jacs.8b09473

  日期：2018.10.31

  This work illustrates the reductive coupling of electron-rich aryl halides with tertiary alkyl halides under Ni-catalyzed cross-electrophile coupling conditions, which offers an efficient protocol for the construction of all carbon quaternary stereogenic centers. The mild and easy-to-operate reaction tolerates a wide range of functional groups. The utility of this method is manifested by the preparation

  这项工作说明了富电子芳基卤化物与叔烷基卤化物在 Ni 催化的交叉亲电偶联条件下的还原偶联，为构建所有碳四元立体中心提供了有效的方案。温和且易于操作的反应可耐受广泛的官能团。该方法的实用性通过环色胺衍生物的制备得到证明，其中成功掺入 7-吲哚基部分特别令人感兴趣，因为许多天然产物由这些关键支架组成。已经进行了 DFT 计算以研究提议的自由基链和双氧化加成途径，这为在溶液中发生的反应部分提供了有用的机理见解。
• NOVEL PYRROLIDINE COMPOUND AND APPLICATION AS MELANOCORTIN RECEPTOR AGONIST
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP3150578B1

  公开（公告）日：2020-10-14
• US9981960B2
  申请人：——

  公开号：US9981960B2

  公开（公告）日：2018-05-29