3-dimethylamino-5-(2,2,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal | 220968-18-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-dimethylamino-5-(2,2,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal
• 英文别名: 3-dimethylamino-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal
• CAS: 220968-18-3
• 化学式: C₁₆H₂₅NO
• 分子量: 247.381
• InChiKey: JFFSMSYJDJYIHZ-OQHNYHKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-5-(2,2,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以85%的产率得到5-(2,6,6-trimethyl-2-cyclohexen-1-yl)ethenylisoxazole
  参考文献：
  名称：

  类视黄醇的新杂环衍生物的合成

  摘要：

  α-和β-紫罗兰酮1和2与二烷基甲酰胺/氯氧化磷的反应提供烯胺6和7以及预期的氯衍生物4和5。的反应图6a与肼，羟胺和胍配吡唑，异恶唑，嘧啶8-10示出这些烯胺酮如在合成类视黄醇的合成中的关键中间体的潜力。

  DOI：

  10.1002/jhet.5570350626
• 作为产物：
  描述：

  alpha-ionone 、 N,N-二甲基甲酰胺 在 sodium hydroxide 、 三氯氧磷 作用下， 生成 3-dimethylamino-5-(2,2,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal
  参考文献：
  名称：

  类视黄醇的新杂环衍生物的合成

  摘要：

  α-和β-紫罗兰酮1和2与二烷基甲酰胺/氯氧化磷的反应提供烯胺6和7以及预期的氯衍生物4和5。的反应图6a与肼，羟胺和胍配吡唑，异恶唑，嘧啶8-10示出这些烯胺酮如在合成类视黄醇的合成中的关键中间体的潜力。

  DOI：

  10.1002/jhet.5570350626

文献信息

• Antiproliferative and Proapoptotic Activities of a New Class of Pyrazole Derivatives in HL-60 Cells
  作者：Maria Anzaldi、Chiara Macciò、Mauro Mazzei、Maria Bertolotto、Luciano Ottonello、Franco Dallegri、Alessandro Balbi

  DOI：10.1002/cbdv.200800354

  日期：2009.10

  A series of N‐substituted pyrazole derivatives have been synthesized and tested for their anticancer effect on the HL‐60 leukaemia cell line. Four were active both in cell‐growth inhibition and in inducing apoptosis. The inhibition of cell growth mainly reflects a compound‐induced reduction in the number of cells in phases from S to M, whereas the induction of apoptosis involves inhibition of expression

  已经合成了一系列 N 取代的吡唑衍生物，并测试了它们对 HL-60 白血病细胞系的抗癌作用。四种在细胞生长抑制和诱导细胞凋亡方面均具有活性。细胞生长的抑制主要反映了化合物诱导的 S 到 M 期细胞数量的减少，而细胞凋亡的诱导涉及 Bcl-2 表达的抑制和 Bax 表达的增强，从而降低了促凋亡半胱天冬酶的激活3.最后，对骨髓性白血病患者的肿瘤细胞进行的初步实验表明，化合物4c、4l、4m和4n确实能够诱导细胞凋亡。
• Synthesis and antimicrobial activity of heterocyclic ionone-like derivatives
  作者：M Anzaldi

  DOI：10.1016/s0223-5234(99)00209-3

  日期：1999.10

  A number of heterocyclic ionone-like derivatives 5 were prepared with appropriate bifunctional reagents by one-pot cyclisation of 3-dimethylamino-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2,4-pentadienal 3a, which was, in turn, obtained from alpha-ionone with N,N-dimethylformamide/phosphorus oxychloride. All compounds 5 possess remarkable activity against the selected Gram-positive, Gramnegative bacterial strains and against Candida albicans. Derivatives 5a2 and 5a6, acting at a high level especially against both Propionibacterium acnes and Staphylococcus aureus, could play a potential role in the treatment of acne and related skin disorders. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• Synthesis and biological evaluation of novel heterocyclic ionone-like derivatives as anti-inflammatory agents
  作者：Alessandro Balbi、Maria Anzaldi、Mauro Mazzei、Mariangela Miele、Maria Bertolotto、Luciano Ottonello、Franco Dallegri

  DOI：10.1016/j.bmc.2006.04.007

  日期：2006.8

  Five- and six-membered heterocyclic ionone-like derivatives 4-6 have been synthesised in one step and with good yield from the key intermediate 3a and appropriate bifunctional reagents. Four were active as inhibitors of the respiratory burst of human neutrophils without affecting cell viability. The two most active compounds (5a,d) tested in neutrophil migration assays, were also found to be potent inhibitors of neutrophil chemotactic responsiveness. These two molecules could be considered as lead compounds of new drugs which can be an effective tool to treat psoriasis and related neutrophilic dermatoses. (c) 2006 Elsevier Ltd. All rights reserved.