5-isobutoxy-4-oxo-4H-chromene-3-carbaldehyde | 1176104-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-isobutoxy-4-oxo-4H-chromene-3-carbaldehyde
• 英文别名: 5-(2-Methylpropoxy)-4-oxochromene-3-carbaldehyde
• CAS: 1176104-91-8
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: QWQMCXSGLDAWMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  5-isobutoxy-4-oxo-4H-chromene-3-carbaldehyde 在 Jones reagent 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到5-isobutoxy-4-oxo-4H-chromene-3-carboxylic acid
  参考文献：
  名称：

  新型色酮类似物对白介素5抑制活性的合成与评价

  摘要：

  合成了一系列新的色酮类似物，并评估了其对白介素5的抑制活性。其中化合物5-环己基甲氧基-3-（4-羟基苄基）-4 H- 铬-4--4-酮（6a，在30μM时抑制率为98％，IC 50 <3.0μM）和5-环己基甲氧基-3-（羟甲基）- 4 H -chromen-4-one（8a，30μM时抑制84％，IC 50 = 7.6μM）表现出最强的活性。具有抑制IL-5抑制活性的色酮类似物的结构要求可以概括为：（i）疏水基团（在环A的第5位的环己基甲氧基）的重要性，（ii）具有较小氢键基团的环B的要求具有给电子性，例如在第4位的酚羟基和（iii）1-4n铬烯环的平面性。

  DOI：

  10.1016/j.ejmech.2010.02.041
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 potassium carbonate 、 sodium iodide 、 三氯氧磷 作用下， 以 水 、 乙腈 为溶剂， 生成 5-isobutoxy-4-oxo-4H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Identification of novel chromenone derivatives as interleukin-5 inhibitors

  摘要：

  A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.007

文献信息

• Synthesis and SAR studies of bis-chromenone derivatives for anti-proliferative activity against human cancer cells
  作者：Eeda Venkateswararao、Vinay K. Sharma、Manoj Manickam、Jieun Yun、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2014.09.057

  日期：2014.11

  A novel family of 3-((4-oxo-4H-chromen-3-yl)methyl)-4H-chromen-4-one (bis-chromone) derivatives were designed, synthesized and studied for their anti-cancer activity using the XTT assay for the growth inhibition against various human cancer cells. Among them, 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-methoxy-4H-chromen-4-one and 3-((5-(cyclohexylmethoxy)-4-oxo-4H-chromen- 3-yl)methyl)-7-hydroxy-4H-chromen-4-one showed micromolar level of in vitro anti-proliferative activity against human cancer cell lines. The SAR studies indicated bis-chromone as a basic scaffold to design anticancer agents. The 5-cyclohexylmethoxy on the first chromenone ring and electron donating group such as CH3, OCH3 or hydrogen bonding group (OH) on the other chromenone ring of bis-chromone increased the activity. However, saturation of one of chromenone to chromanone in bis-chromones decreased the activity. (C) 2014 Elsevier Ltd. All rights reserved.
• Identification of novel chromenone derivatives as interleukin-5 inhibitors
  作者：Eeda Venkateswararao、Min-Seok Kim、Vinay K. Sharma、Ki-Cheul Lee、Santhosh Subramanian、Eunmiri Roh、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2012.11.007

  日期：2013.1

  A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and evaluation of novel chromone analogs for their inhibitory activity against interleukin-5
  作者：Pillaiyar Thanigaimalai、Tuan Anh Le Hoang、Ki-Cheul Lee、Vinay K. Sharma、Seong-Cheol Bang、Jun Ho Yun、Eunmiri Roh、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2010.02.041

  日期：2010.6

  A novel series of chromone analogs were synthesized and evaluated for their inhibitory activity against interleukin-5. Among them compounds 5-Cyclohexylmethoxy-3-(4-hydroxybenzyl)-4H-chromen-4-one (6a, 98% inhibition at 30 μM, IC50 < 3.0 μM) and 5-Cyclohyxylmethoxy-3-(hydroxymethyl)-4H-chromen-4-one (8a, 84% inhibition at 30 μM, IC50 = 7.6 μM) showed most potent activity. The structural requirement

  合成了一系列新的色酮类似物，并评估了其对白介素5的抑制活性。其中化合物5-环己基甲氧基-3-（4-羟基苄基）-4 H- 铬-4--4-酮（6a，在30μM时抑制率为98％，IC 50 <3.0μM）和5-环己基甲氧基-3-（羟甲基）- 4 H -chromen-4-one（8a，30μM时抑制84％，IC 50 = 7.6μM）表现出最强的活性。具有抑制IL-5抑制活性的色酮类似物的结构要求可以概括为：（i）疏水基团（在环A的第5位的环己基甲氧基）的重要性，（ii）具有较小氢键基团的环B的要求具有给电子性，例如在第4位的酚羟基和（iii）1-4n铬烯环的平面性。