2-cyano-N-cyclohexyl-N-methyl-acetamide | 15059-90-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-cyano-N-cyclohexyl-N-methyl-acetamide
• 英文别名: N-Cyanacetyl-N-methyl-cyclohexylamin；Cyanessigsaeure-cyclohexyl-methyl-amid；2-cyano-N-cyclohexyl-N-methyl-propionamide；2-cyano-N-cyclohexyl-N-methylacetamide
• CAS: 15059-90-2
• 化学式: C₁₀H₁₆N₂O
• mdl: MFCD09945264
• 分子量: 180.25
• InChiKey: QWXZDXBIPFRDGO-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  330.8±21.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-cyano-N-cyclohexyl-N-methyl-acetamide 在 Raney nickel 氨 、 氢气 作用下， 以 甲醇 为溶剂， 生成 3-amino-N-cyclohexyl-N-methyl-propionamide
  参考文献：
  名称：

  [EN] 2-AMINO-QUINAZOLINE DERIVATIVES USEFUL AS INHIBITORS OF B-SECRETASE (BACE)
  [FR] DERIVES DE 2-AMINO-QUINAZOLINE UTILES EN TANT QU'INHIBITEURS DE B-SECRETASE (BACE)

  摘要：

  本发明涉及新型2-氨基-3,4-二氢喹唑啉衍生物，包含它们的药物组合物以及其在治疗阿尔茨海默病（AD）和相关疾病中的用途。该发明的化合物是ß-分泌酶抑制剂，也称为ß-位点裂解酶和BACE。

  公开号：

  WO2006024932A1
• 作为产物：
  描述：

  N-甲基环己胺 、 氰乙酸乙酯 以 乙醇 为溶剂， 生成 2-cyano-N-cyclohexyl-N-methyl-acetamide
  参考文献：
  名称：

  吡啶甲酰胺利尿剂。二。4，6-二氨基-5-亚硝基嘧啶与N-取代的氰基乙酰胺的反应。

  摘要：

  DOI：

  10.1021/jm00314a008

文献信息

• [EN] NOVEL 2-AMINO-QUINAZOLINE DERIVATIVES USEFUL AS INHIBITORS OF ß-SECRETASE (BACE)<br/>[FR] NOUVEAUX DERIVES DE 2-AMINO-QUINAZOLINE UTILES EN TANT QU'INHIBITEURS DE LA $G(B)-SECRETASE (BACE)
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006017844A1

  公开（公告）日：2006-02-16

  The present invention is directed to novel 2-amino-3,4-dihydro-quinazoline derivatives, pharmaceutical compositions containing them and their use in the treatment of Alzheimer’s disease (AD) and related disorders. The compounds of the invention are inhibitors of β-secretase, also known as β-site cleaving enzyme and BACE.

  本发明涉及新颖的2-氨基-3,4-二氢喹唑啉衍生物，包含它们的药物组合物以及它们在治疗阿尔茨海默病（AD）和相关疾病中的用途。本发明的化合物是β-分泌酶的抑制剂，也被称为β-位点裂解酶和BACE。
• Design, Synthesis, and Anti-Neuroinflammatory Activity of Amide- Containing Dithiolethiones
  作者：Karrington Craig、Paula Avila、Dennis A. Brown

  DOI：10.2174/1573406416666200909105100

  日期：2021.12

  Multiple sclerosis (MS) is a chronic immune-mediated disease of the central nervous system characterized by demyelination of neurons and neurodegeneration. Current MS therapies ameliorate inflammatory damage but are unable to address the degenerative aspects of the disease.

  In this report, we evaluate the ability of amide-based dithiolethiones (DTTs) to suppress neuroinflammation in microglia and increase anti-oxidant capacity in neuron-like cells.

  A series of amide-containing DTTs were designed, synthesized, and assayed for the ability to suppress pro-neuroinflammatory cytokines IL-12p40 and IL-23p19 induced by LPS in the BV2 microglial cell line. Lead analog 2c was identified and further characterized.

  Structure-activity data revealed tolerance towards a variety of amides. Morpholine analog 2c dose-dependently reduced various other inflammatory cytokines and mediators, including TNF, IL-6, IL-1β, NOS2, and COX2. Additionally, 2c elevated cellular levels of glutathione in SH-SH5Y neuronal cell line. Furthermore, mechanistic studies showed that 2c increased the expression of antiinflammatory Nrf2 and HMOX proteins.

  The combination of anti-neuroinflammatory and anti-oxidant activities of amide-based DTTs suggests that they are promising agents for the treatment of both demyelination and neurodegeneration in MS.

  背景：多发性硬化症（MS）是一种慢性免疫介导的中枢神经系统疾病，其特征是神经元的髓鞘脱失和神经退行性。目前的MS治疗方法能够缓解炎症损伤，但无法解决疾病的退行性方面。 目标：在本报告中，我们评估了酰胺基二硫乙烯硫醚（DTTs）抑制微胶质细胞中的神经炎症和增加神经样细胞抗氧化能力的能力。 方法：设计、合成一系列含酰胺的DTTs，并对其抑制BV2微胶质细胞系中LPS诱导的前神经炎症细胞因子IL-12p40和IL-23p19的能力进行分析。鉴定并进一步表征了主导类似物2c。 结果：结构活性数据显示对各种酰胺具有耐受性。吗啉类似物2c剂量依赖性地减少了其他各种炎症细胞因子和介质，包括TNF、IL-6、IL-1β、NOS2和COX2。此外，2c提高了SH-SH5Y神经细胞系中谷胱甘肽的细胞水平。此外，机械研究表明，2c增加了抗炎Nrf2和HMOX蛋白的表达。 结论：基于酰胺的DTTs具有抗神经炎症和抗氧化活性的组合表明它们是治疗MS中髓鞘脱失和神经退行性的有前景的药物。
• Novel 2-amino-quinazoline derivatives useful as inhibitors of beta-secretase (BACE)
  申请人：Bischoff Paul Francois

  公开号：US20060178383A1

  公开（公告）日：2006-08-10

  The present invention is directed to novel 2-amino-3,4-dihydro-quinazoline derivatives, pharmaceutical compositions containing them and their use in the treatment of Alzheimer's disease (AD) and related disorders. The compounds of the invention are inhibitors of β-secretase, also known as β-site cleaving enzyme and BACE.

  本发明涉及新型2-氨基-3,4-二氢喹唑啉衍生物、含有它们的制药组合物以及它们在治疗阿尔茨海默病（AD）和相关疾病中的应用。本发明的化合物是β-秘鲁酶的抑制剂，也称为β-位点裂解酶和BACE。
• 2-amino-quinazoline derivatives useful as inhibitors of β-secretase (BACE)
  申请人：Baxter Ellen

  公开号：US08383637B2

  公开（公告）日：2013-02-26

  The present invention is directed to novel 2-amino-3,4-dihydro-quinazoline derivatives, pharmaceutical compositions containing them and their use in the treatment of Alzheimer's disease (AD) and related disorders. The compounds of the invention are inhibitors of β-secretase, also known as β-site cleaving enzyme and BACE.

  本发明涉及新型2-氨基-3,4-二氢喹唑啉衍生物，包含它们的制药组合物以及它们在治疗阿尔茨海默病（AD）和相关疾病中的用途。本发明的化合物是β-分泌酶抑制剂，也称为β-位点裂解酶和BACE。
• [EN] 2-AMINO-QUINAZOLINE DERIVATIVES USEFUL AS INHIBITORS OF BETA-SECRETASE (BACE)<br/>[FR] NOUVEAUX DERIVES DE 2-AMINO-QUINAZOLINE UTILES EN TANT QU'INHIBITEURS DE LA $G(B)-SECRETASE (BACE)
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006017836A3

  公开（公告）日：2006-06-29