2-氯-1-(2-哌啶-1-基-1,3-硒唑-5-基)乙酮 | 883992-48-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氯-1-(2-哌啶-1-基-1,3-硒唑-5-基)乙酮
• 英文名称: 5-chloroacetyl-2-piperidino-1,3-selenazole
• 英文别名: 2-Chloro-1-[2-(piperidin-1-yl)-1,3-selenazol-5-yl]ethan-1-one；2-chloro-1-(2-piperidin-1-yl-1,3-selenazol-5-yl)ethanone
• CAS: 883992-48-1
• 化学式: C₁₀H₁₃ClN₂OSe
• 分子量: 291.639
• InChiKey: NULCUFKUILSQTF-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  406.4±43.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二氯丙酮 、 N¹,N¹-dimethyl-N²-(piperidinoselenocarbonyl)formamidine 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到2-氯-1-(2-哌啶-1-基-1,3-硒唑-5-基)乙酮
  参考文献：
  名称：

  硒氮杂二烯与α-卤代酮反应制备5-酰基-2-氨基-1,3-硒唑

  摘要：

  硒氮杂二烯与 α-卤代酮反应以高产率生成 5-酰基-2-氨基-1,3-硒唑。

  DOI：

  10.1055/s-2005-921752

文献信息

• 5-Chloroacetyl-2-amino-1,3-selenazoles attenuate microglial inflammatory responses through NF-κB inhibition
  作者：Kyong Nyon Nam、Mamoru Koketsu、Eunjoo H. Lee

  DOI：10.1016/j.ejphar.2008.03.034

  日期：2008.7

  Microglia are the prime effector cells involved in immune and inflammatory responses in the central nervous system (CNS). In pathological conditions, microglia are activated to restore CNS homeostasis. However, clmoniC microglial activation endangers neuronal survival through the release of various toxic proinflammatory molecules. Thus, negative regulators of microglial activation have been identified as potential therapeutic candidates in many neurological diseases. A number of selenium-containing compounds show antioxidant activity. In this study, we investigated 2-amino-13-selenazole derivatives with regard to anti-inflammatory activity or inhibitory effects on microglial activation. Among 26 derivatives of 2-amino-1,3-selenazole and bis-(2-amino-5-selenazoyl) ketones, we observed that 5-chloroacetyl-2-piperidino-1,3-selenazole (CS]) and 5-chloi-oacetyl-2-morpholino-1,3-seleiiazole (CS2) strongly inhibited I i popolysaccha ride (LPS)-induced nitric oxide (NO) release from BV2 microglial cells. In rat primary cultured microglia, CS1 and CS2 significantly reduced LPS-incluced production of NO, tumor necrosis factor (TNF)-alpha, and prostaglandin E-2. Real-time reverse transcription-polymerase chain reaction analysis revealed that the pretreatment of primary microglial cells with CS1 and CS2 attenuated LPS-induced mRNA expression for inducible NO synthase, TNF-alpha, interleukin-1 beta, and cyclooxygenase-2. In addition, CS1 and CS2 Suppressed LPS-induced activation of nuclear factor-kappa B and Akt. These results suggest that CS1 and CS2 may provide neuroprotection by suppressing the proinflammatory pathway in activated microglia. (C) 2008 Published by Elsevier B.V.
• Preparation of 5-Acyl-2-amino-1,3-selenazoles by the Reaction of Selenazadienes with α-Haloketone
  作者：Mamoru Koketsu、Hideharu Ishihara、Masakazu Kogami、Hiromune Ando

  DOI：10.1055/s-2005-921752

  日期：——

  Reaction of selenazadienes with α-haloketones gave 5-acyl-2-amino-1,3-selenazoles in high yields.

  硒氮杂二烯与 α-卤代酮反应以高产率生成 5-酰基-2-氨基-1,3-硒唑。