1-(4-(dimethylamino)phenyl)-5-hydroxyhexa-1,4-dien-3-one | 1229618-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-(dimethylamino)phenyl)-5-hydroxyhexa-1,4-dien-3-one
• CAS: 1229618-85-2
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: STCOHZXRWGHCOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-(dimethylamino)phenyl)-5-hydroxyhexa-1,4-dien-3-one 、 5-氟-2-甲氧基苯甲醛 在 boron trioxide 、 硼酸三丁酯 、 哌啶 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 1-(4-(dimethylamino)phenyl)-7-(5-fluoro-2-methoxyphenyl)hepta-1,6-diene-3,5-ione
  参考文献：
  名称：

  COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR

  摘要：

  描述了由小分子、基质和孤立细胞组成的组合物，包括制备方法，以及动物细胞分化、转分化和增殖成骨母细胞谱系的方法。给细胞施加的或与细胞共培养的成骨材料的示例由独立或首选与基质组合的Formula II、IV和VI化合物代表。受小分子刺激的细胞还与基质结合，与细胞粘合剂或材料载体一起植入到动物体内的部位进行骨修复。预先用Formula II、IV和VI化合物处理的基质也被用于导致细胞迁移到用于治疗目的的基质上。

  公开号：

  US20160038641A1
• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 乙酰丙酮 在 boron trioxide 、 硼酸三丁酯 、 正丁胺 作用下， 以 乙酸乙酯 为溶剂， 反应 2.5h， 生成 1-(4-(dimethylamino)phenyl)-5-hydroxyhexa-1,4-dien-3-one
  参考文献：
  名称：

  COMPOUNDS AND MATRICES FOR USE IN BONE GROWTH AND REPAIR

  摘要：

  描述了由小分子、基质和孤立细胞组成的组合物，包括制备方法，以及动物细胞分化、转分化和增殖成骨母细胞谱系的方法。给细胞施加的或与细胞共培养的成骨材料的示例由独立或首选与基质组合的Formula II、IV和VI化合物代表。受小分子刺激的细胞还与基质结合，与细胞粘合剂或材料载体一起植入到动物体内的部位进行骨修复。预先用Formula II、IV和VI化合物处理的基质也被用于导致细胞迁移到用于治疗目的的基质上。

  公开号：

  US20160038641A1

文献信息

• SMALL MOLECULE IMMUNOMODULATORS FOR ALZHEIMER'S DISEASE
  申请人：Cashman John R.

  公开号：US20120040976A1

  公开（公告）日：2012-02-16

  Disclosed are methods for identifying individuals suffering from a CNS disorder (including Alzheimer's Disease, ALS, behavioral disorders, and the like) that could be treated with a CNS drug with greater therapeutic efficacy and lower side effects and the compounds useful for such treatment. Also disclosed are methods for predicting the efficacy of a drug candidate for the treatment of a CNS disorder. The technology is also applicable to drug discovery for evaluation in animal models of neurodegenerative diseases.

  本发明涉及识别患有中枢神经系统疾病（包括阿尔茨海默病、肌萎缩性侧索硬化症、行为障碍等）的个体，这些个体可以通过使用中枢神经系统药物进行治疗，其治疗效果更好，副作用更小，以及用于此类治疗的化合物。本发明还涉及预测治疗中枢神经系统疾病的候选药物的疗效的方法。该技术还适用于药物发现，以在神经退行性疾病动物模型中进行评估。
• Evaluation <i>in Vitro</i> of Synthetic Curcumins As Agents Promoting Monocytic Gene Expression Related to β-Amyloid Clearance
  作者：S. Gagliardi、S. Ghirmai、K. J. Abel、M. Lanier、S. J. Gardai、C. Lee、J. R. Cashman

  DOI：10.1021/tx200246t

  日期：2012.1.13

  Accumulation of amyloid-beta (A beta) is one of the hallmarks of Alzheimer's disease (AD), and efficient clearance of A beta by cells of the innate immune system may be an important mechanism. for controlling or preventing disease onset. It was reported that peripheral blood mononuclear cells (PBMCs) of most AD patients are defective in the phagocytosis of soluble A beta. Natural curcumins were shown to restore A beta phagocytosis by AD PBMCs and to up-regulate the expression of key genes including MGAT3 and those encoding Toll-like receptors (TLRs). Bisdemethoxycurcumin (BDC), a minor component of natural curcumin, was shown to have the greatest potency for stimulating AD PBMCs. Because natural curcumins have inherent limitations with regard to physicochemical properties, synthetic curcumin analogues were developed that. showed improved solubility, stability, and bioavailability. An in vitro system using human monocytic cell lines (U-937, THP-1) was used to evaluate analogues for the potency. of innate immune cell stimulation. These cell lines showed responses to curcuminoids and to 1 alpha,25-dihydroxyvitamin D3 (VD3) resembling those seen in human PBMCs. From more than 45 curcuminoids analyzed, the most potent compounds possessing enhanced pharmaceutical properties were identified. The most promising candidates included prodrug versions containing water solubility-enhancing amino acids and stability-increasing modifications near the central diketone. In vivo studies showed compound (5) substantially increased bioavailability by combining several promising structural modifications. Studies examining ex vivo phagocytosis of A beta and bead particles in mouse microglia showed that BDC and several water-soluble analogues were quite effective compared to curcumin or an unnatural analogue. In vitro studies using monocytic cell lines reported herein complement those using human PBMCs and represent a routinely accessible and uniform cellular resource allowing direct comparisons between compounds.