8-sec-butyl-3-(4-methoxyphenyl)-2-oxo-2H-chromene-6-carbaldehyde | 1290078-33-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-sec-butyl-3-(4-methoxyphenyl)-2-oxo-2H-chromene-6-carbaldehyde
• 英文别名: 8-Butan-2-yl-3-(4-methoxyphenyl)-2-oxochromene-6-carbaldehyde
• CAS: 1290078-33-9
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: BSWNLVCXNXSRBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-sec-butyl-3-(4-methoxyphenyl)-2-oxo-2H-chromene-6-carbaldehyde 在 4-二甲氨基吡啶 、 aluminum (III) chloride 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 (±)-11-amino-12-(8-(sec-butyl)-3-(4-methoxyphenyl)-2-oxo-2H-chromen-6-yl)-3,3-dimethyl-2,3,4,7,8,9,10,12-octahydro-1H-chromeno[2,3-b]quinolin-1-one
  参考文献：
  名称：

  Discovery of 3-Arylcoumarin-tetracyclic Tacrine Hybrids as Multifunctional Agents against Parkinson’s Disease

  摘要：

  A series of multifunctional directed 3-arylcoumarin-tetracyclic tacrine derivatives was designed and synthesized for the treatment of Parkinson's disease (PD). A number of derivatives (18, 19, 20, 21, and 24) demonstrated significant reduction of aggregation of "human" alphasynuclein (a-synuclein) protein, expressing on transgenic Caenorhabditis elegans (C. elegans) model NL5901. Moreover, compounds 16, 18, and 24 also exhibited good antioxidant properties and significantly increased the dopamine (DA) content in N2 and NL5901 strains of C. elegans. Interestingly, the protective efficacy of these hybrids seems to be mediated via activation of longevity promoting transcription factor DAF-16. In addition, molecular modeling studies have evidenced the exquisite interaction of most active compounds 18 and 24 with asynuclein protein. Taken together, the data indicate that the derivatives may be useful leads against aging and age associated PD.

  DOI：

  10.1021/ml500222g
• 作为产物：
  描述：

  2-仲丁基苯酚 在 N-甲基吗啉 、 三聚氯氰 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.92h， 生成 8-sec-butyl-3-(4-methoxyphenyl)-2-oxo-2H-chromene-6-carbaldehyde
  参考文献：
  名称：

  Discovery of 3-Arylcoumarin-tetracyclic Tacrine Hybrids as Multifunctional Agents against Parkinson’s Disease

  摘要：

  A series of multifunctional directed 3-arylcoumarin-tetracyclic tacrine derivatives was designed and synthesized for the treatment of Parkinson's disease (PD). A number of derivatives (18, 19, 20, 21, and 24) demonstrated significant reduction of aggregation of "human" alphasynuclein (a-synuclein) protein, expressing on transgenic Caenorhabditis elegans (C. elegans) model NL5901. Moreover, compounds 16, 18, and 24 also exhibited good antioxidant properties and significantly increased the dopamine (DA) content in N2 and NL5901 strains of C. elegans. Interestingly, the protective efficacy of these hybrids seems to be mediated via activation of longevity promoting transcription factor DAF-16. In addition, molecular modeling studies have evidenced the exquisite interaction of most active compounds 18 and 24 with asynuclein protein. Taken together, the data indicate that the derivatives may be useful leads against aging and age associated PD.

  DOI：

  10.1021/ml500222g

文献信息

• Efficient and General Synthesis of 3-Aryl Coumarins Using Cyanuric Chloride¹
  作者：Koneni Sashidhara、Gopala Palnati、Srinivasa Avula、Abdhesh Kumar

  DOI：10.1055/s-0031-1290344

  日期：2012.3

  protocol for a rapid synthesis of different substituted 3-aryl coumarins is reported. A series of different substituted phenyl acetic acids have been successfully reacted with different substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) and N-methyl morpholine to afford 3-aryl coumarins in good to excellent yields. synthesis - 3-aryl coumarins -

  报道了快速合成不同取代的3-芳基香豆素的有效且通用的方案。在氰尿酰氯（2,4,6-三氯-1,3,5-三嗪）和N-甲基吗啉的存在下，一系列不同的取代苯基乙酸已成功与不同的取代的2-羟基苯甲醛反应，得到3芳基香豆素的收率高至优异。 合成-3-芳基香豆素-氰尿酰氯-2-羟基苯甲醛 系列“新型合成方法论研究”的第八部分。
• Design and synthesis of new series of coumarin–aminopyran derivatives possessing potential anti-depressant-like activity
  作者：Koneni V. Sashidhara、Ram K. Modukuri、Seema Singh、K. Bhaskara Rao、G. Aruna Teja、Sampa Gupta、Shubha Shukla

  DOI：10.1016/j.bmcl.2014.11.036

  日期：2015.1

  A new series of coumarin based aminopyran derivatives were designed, synthesized and evaluated for their preclinical antidepressant effect on Swiss albino mice. Among the series, compounds 21, 25, 26, 27, 32 and 33 exhibited significant activity profile in forced swimming test (FST). Compound 27 was most efficacious, which at a very low dose of 0.5 mg/kg reduced the time of immobility by 86.5% as compared to the standard drug fluoxetine (FXT) which reduced the immobility time by 69.8% at the dose of 20 mg/kg, ip. In addition, all active compounds were screened in dose dependent manner (at doses of 0.25, 0.5, 1 mg/kg ip) in FST and tail suspension test (TST). Interestingly, all active compounds did not caused any significant alteration of locomotor activity in mice as compared to control, indicating that the hybrids did not produce any motor impairment effects. The results indicate that coumarin-aminopyran derivatives may have potential therapeutic value for the management of mental depression. (C) 2014 Elsevier Ltd. All rights reserved.
• Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents
  作者：Koneni V. Sashidhara、Abdhesh Kumar、Manavi Chatterjee、K. Bhaskara Rao、Seema Singh、Anil Kumar Verma、Gautam Palit

  DOI：10.1016/j.bmcl.2011.02.040

  日期：2011.4

  A series of 3-phenylcoumarins were synthesized and screened for potential antidepressant activity by tail suspension test (TST) in mice. Three compounds (6, 7 and 13) exhibited impressive antidepressant activity, measured in terms of percentage decrease in immobility duration (% DID). In addition, the active antidepressant compounds were subsequently studied at their most effective dose and activity of these compounds were confirmed in forced swimming test (FST) animal model, in which the compounds at a low dose of 0.5 mg/kg significantly decreased the immobility time and exhibited greater efficacy than the reference standards fluoxetine and imipramine. The potent compounds did not show any neurotoxicity in the rotarod test and the preliminary results are promising enough to warrant further studies around this scaffold. (C) 2011 Elsevier Ltd. All rights reserved.