8-methyl-2-oxo-3-(3,4,5-trimethoxyphenyl)-2H-chromene-6-carbaldehyde | 1290078-29-3

• 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-methyl-2-oxo-3-(3,4,5-trimethoxyphenyl)-2H-chromene-6-carbaldehyde
• 英文别名: 8-Methyl-2-oxo-3-(3,4,5-trimethoxyphenyl)chromene-6-carbaldehyde
• CAS: 1290078-29-3
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: PRUSKIHWCMMUGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-methyl-2-oxo-3-(3,4,5-trimethoxyphenyl)-2H-chromene-6-carbaldehyde 在 甲醇 、 sodium tetrahydroborate 、 三溴化磷 作用下， 以 苯 为溶剂， 反应 0.58h， 生成 6-(bromomethyl)-8-methyl-3-(3,4,5-trimethoxyphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and evaluation of new 3-phenylcoumarin derivatives as potential antidepressant agents

  摘要：

  A series of amine substituted 3-phenyl coumarin derivatives were designed and synthesized as potential antidepressant agents. In preliminary screening, all compounds were evaluated in forced swimming test (FST), a model to screen antidepressant activity in rodents. Among the series, compounds 5c and 6a potentially decreased the immobility time by 73.4% and 79.7% at a low dose of 0.5 mg/kg as compared to standard drug fluoxetine (FXT) which reduced the immobility time by 74% at a dose of 20 mg/kg, ip. Additionally, these active compounds also exhibited significant efficacy in tail suspension test (TST) (another model to screen antidepressant compounds). Interestingly, rotarod and locomotor activity tests confirmed that these two compounds do not have any motor impairment effect and neurotoxicity in mice. Our studies demonstrate that the new 3-phenylcoumarin derivatives may serve as a promising antidepressant lead and hence pave the way for further investigation around this chemical space. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.08.037
• 作为产物：
  描述：

  邻甲酚 在 N-甲基吗啉 、 三聚氯氰 作用下， 以 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 10.92h， 生成 8-methyl-2-oxo-3-(3,4,5-trimethoxyphenyl)-2H-chromene-6-carbaldehyde
  参考文献：
  名称：

  Discovery of coumarin–monastrol hybrid as potential antibreast tumor-specific agent

  摘要：

  Development of new, targeted antibreast cancer drug which can treat both the hormone receptor (positive and negative) breast cancers is a very challenging task. The concept of molecular hybridization led us to discover a novel class of coumarin monastrol hybrid, as a novel breast cancer agent which selectively induce apoptosis in both primary and metastatic breast cancer cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.044

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。
• Hybrids of coumarin–indole: design, synthesis and biological evaluation in Triton WR-1339 and high-fat diet induced hyperlipidemic rat models
  作者：Koneni V. Sashidhara、K. Bhaskara Rao、Ravi Sonkar、Ram K. Modukuri、Yashpal S. Chhonker、Pragati Kushwaha、Hardik Chandasana、A. K. Khanna、Rabi S. Bhatta、Gitika Bhatia、Manish Kumar Suthar、Jitendra Kumar Saxena、Vikash Kumar、Mohammad Imran Siddiqi

  DOI：10.1039/c6md00283h

  日期：——

  Lipid lowering activity of novel coumarin–indole hybrids has been demonstrated.

  新型香豆素-吲哚杂合物的降脂活性已被证实。
• 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 of coumarin–monastrol hybrid as potential antibreast tumor-specific agent
  作者：Koneni V. Sashidhara、Srinivasa Rao Avula、Komal Sharma、Gopala Reddy Palnati、Surendar Reddy Bathula

  DOI：10.1016/j.ejmech.2012.11.044

  日期：2013.2

  Development of new, targeted antibreast cancer drug which can treat both the hormone receptor (positive and negative) breast cancers is a very challenging task. The concept of molecular hybridization led us to discover a novel class of coumarin monastrol hybrid, as a novel breast cancer agent which selectively induce apoptosis in both primary and metastatic breast cancer cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Discovery of coumarin-dihydroquinazolinone analogs as niacin receptor 1 agonist with in-vivo anti-obesity efficacy
  作者：L. Ravithej Singh、Ajeet Kumar、Akanksha Upadhyay、Sampa Gupta、Gopala Reddy Palanati、Kamakshi Sikka、Mohammad Imran Siddiqi、Prem N. Yadav、Koneni V. Sashidhara

  DOI：10.1016/j.ejmech.2018.04.037

  日期：2018.5

  In this study, we presented rational designing and synthesis of coumarin-dihydroquinazolinone conjugates to evaluate their agonist activity at GPR109a receptor. Among the synthesized small molecule library, compound 10c displayed robust agonist action at GPR109a with EC50 < 11 nM. Homology model of human GPR109a protein was generated to realize the binding interaction of the active molecule with the active site of GPR109a. Further, the efficacy of active compound 10c was supported by in -vivo experiments which showed reduced body weight in diet induced obese mice model. Interestingly, compound 10c reduced leptin in blood plasma and total serum cholesterol. These results suggest that the coumarin-dihydroquinazolinone conjugate is a suitable scaffold to further expand the chemical diversity and make them potential niacin receptor 1 agonist. (C) 2018 Elsevier Masson SAS. All rights reserved.