2-(4-甲基-哌嗪-1-基)-1-苯基-乙酮 | 41298-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(4-甲基-哌嗪-1-基)-1-苯基-乙酮
• 英文名称: 2-(4-methylpiperazin-1-yl)-1-phenylethan-1-one
• 英文别名: 2-(4-methylpiperazin-1-yl)-1-phenylethanone；2-(4-methyl-piperazin-1-yl)-1-phenyl-ethanone；2-(4-methyl-piperazino)-1-phenyl-ethanone；2-(4-Methyl-piperazino)-1-phenyl-aethanon；N-Methyl-N'-phenacylpiperazine
• CAS: 41298-85-5
• 化学式: C₁₃H₁₈N₂O
• mdl: MFCD00470296
• 分子量: 218.299
• InChiKey: LJTXXCLPBZQLHW-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  156-157 °C(Press: 3.5 Torr)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-甲基-哌嗪-1-基)-1-苯基-乙酮 在 苯基溴化镁 作用下， 生成 1-benzyl-4-(2-hydroxy-2,2-diphenyl-ethyl)-1-methyl-piperazinium; bromide
  参考文献：
  名称：

  Tertiary Carbinols of the Piperazine Series. I

  摘要：

  DOI：

  10.1021/ja01544a047
• 作为产物：
  描述：

  1-methyl-4-[(2S,3S)-3-phenyloxiran-2-yl]sulfonylpiperazine 以 二甲基亚砜 为溶剂， 反应 264.0h， 生成 N-甲基哌嗪 、 2-(4-甲基-哌嗪-1-基)-1-苯基-乙酮
  参考文献：
  名称：

  New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides

  摘要：

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.

  DOI：

  10.1021/jm00395a010

文献信息

• Expeditious one-pot synthesis of C3-piperazinyl-substituted quinolines: key precursors to potent c-Met inhibitors
  作者：Yuanxiang Wang、Jing Ai、Gang Liu、Meiyu Geng、Ao Zhang

  DOI：10.1039/c1ob05830d

  日期：——

  An effective one-pot synthesis of quinolines bearing diverse C3-piperazinyl functions was developed by using a modified Friedländer's protocol. The method not only enables the synthesis of our early reported c-Met inhibitor on a large scale, but also provides a way to generate novel multi-substituted quinolines for further structure–activity relationship (SAR) study.

  一种有效的单锅合成具有多样化C3-哌嗪基团的喹啉的方法被开发出来，采用了改进的Friedländer反应。该方法不仅能够大规模合成我们早期报道的c-Met抑制剂，还为生成新型多取代喹啉提供了一种途径，以便进一步进行结构-活性关系（SAR）研究。
• One pot synthesis of <scp> α‐ <i>N</i> </scp> ‐heteroaryl ketone derivatives from aryl ketones using aqueous <scp> NaICl ₂ </scp>
  作者：Shrikant M. Ghodse、Navnath T. Hatvate、Vikas N. Telvekar

  DOI：10.1002/jhet.4412

  日期：2022.4

  A simple and efficient method for the synthesis of α-heteroaryl ketones from aryl ketones and amine using aqueous sodium dichloroiodate is established. This method is mild, operationally simple, has a short reaction time, and easy workup procedure to afford the corresponding α-N-heteroaryl ketone derivatives in moderate to good yield.

  建立了一种使用二氯碘酸钠水溶液从芳基酮和胺合成α-杂芳基酮的简单有效的方法。该方法温和、操作简单、反应时间短、后处理容易，以中等至良好的收率得到相应的α- N-杂芳基酮衍生物。
• Small-Molecule Activator of UNC-51-Like Kinase 1 (ULK1) That Induces Cytoprotective Autophagy for Parkinson’s Disease Treatment
  作者：Liang Ouyang、Lan Zhang、Shouyue Zhang、Dahong Yao、Yuqian Zhao、Guan Wang、Leilei Fu、Peng Lei、Bo Liu

  DOI：10.1021/acs.jmedchem.7b01575

  日期：2018.4.12

  UNC-51-like kinase 1 (ULK1), the yeast Atg1 ortholog, is the sole serine-threonine kinase and initiating 1, enzyme in autophagy, which may be regarded as a target in Parkinson's disease (PD). Herein, we discovered a small molecule 33i (BL-918) as a potent activator of ULK1 by structure-based drug design. Subsequently, some key amino acid residues (Arg18, Lys50, Asn86, and Tyr89) were found to be crucial to the binding pocket between ULK1 and 33i by site-directed mutagenesis. Moreover, we found that 33i induced autophagy via the ULK complex in SH-SYSY cells. Intriguingly, this activator displayed a cytoprotective effect on MPP+-treated SH-SYSY cells, as well as protected against MPTP-induced motor dysfunction and loss of dopaminergic neurons by targeting ULK1-modulated autophagy in mouse models of PD. Together, these results demonstrate the therapeutic potential to target ULK1, and 33i, the novel activator of ULK1, may serve as a candidate drug for future PD treatment.
• New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides
  作者：Marie Josephe Brienne、Daniel Varech、Martine Leclercq、Jean Jacques、Nathalie Radembino、Christine Dessalles、Georges Mahuzier、Chantal Gueyouche、Christian Bories

  DOI：10.1021/jm00395a010

  日期：1987.12

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.
• US3951982A
  申请人：——

  公开号：US3951982A

  公开（公告）日：1976-04-20

表征谱图