3-hexyl-7-hydroxy-4-oxo-4H-1-benzopyran | 1422515-82-9

• 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: 3-hexyl-7-hydroxy-4-oxo-4H-1-benzopyran
• 英文别名: 3-Hexyl-7-hydroxychromen-4-one
• CAS: 1422515-82-9
• 化学式: C₁₅H₁₈O₃
• 分子量: 246.306
• InChiKey: BQTQNPFFZHQBDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-溴十一酰氯 、 3-hexyl-7-hydroxy-4-oxo-4H-1-benzopyran 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 N,N,N-triethyl-11-(3-hexyl-4-oxo-4H-chromen-7-yloxy)-11-oxoundecan-1-aminium bromide
  参考文献：
  名称：

  Synthesis, Antiproliferative, and c-Src Kinase Inhibitory Activities of 4-Oxo-4H-1-benzopyran Derivatives

  摘要：

  A new class of 4‐oxo‐4H‐1‐benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA‐MB‐468), ovarian adenocarcinoma (SK‐OV‐3), and colorectal adenocarcinoma (HT‐29). Two compounds, that is, 3‐hexyl‐7,8‐dihydroxy‐4‐oxo‐4H‐1‐benzopyran and (E)‐ethyl 3‐(7‐methoxy‐4‐oxo‐4H‐1‐benzopyran‐3‐yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52–57 μM). Structure‐activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.

  DOI：

  10.1002/jhet.2106
• 作为产物：
  描述：

  间苯二酚 在 三氟化硼乙醚 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 3-hexyl-7-hydroxy-4-oxo-4H-1-benzopyran
  参考文献：
  名称：

  Synthesis, Antiproliferative, and c-Src Kinase Inhibitory Activities of 4-Oxo-4H-1-benzopyran Derivatives

  摘要：

  A new class of 4‐oxo‐4H‐1‐benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA‐MB‐468), ovarian adenocarcinoma (SK‐OV‐3), and colorectal adenocarcinoma (HT‐29). Two compounds, that is, 3‐hexyl‐7,8‐dihydroxy‐4‐oxo‐4H‐1‐benzopyran and (E)‐ethyl 3‐(7‐methoxy‐4‐oxo‐4H‐1‐benzopyran‐3‐yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52–57 μM). Structure‐activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.

  DOI：

  10.1002/jhet.2106

文献信息

• Ammonium derivatives of chromenones and quinolinones as lead antimicrobial agents
  作者：SHILPI GUPTA、SEEMA SINGH、ABHA KATHURIA、MANISH KUMAR、SWETA SHARMA、RAM KUMAR、VIRINDER S PARMAR、BHARAT SINGH、ANJALI GUPTA、ERIK VAN DER EYCKEN、GAINDA L SHARMA、SUNIL K SHARMA

  DOI：10.1007/s12039-011-0147-7

  日期：2012.3

  A series of novel ammonium derivatives were synthesized and examined for their antimicrobial efficacy. Comparison of antimicrobial spectrum revealed that compounds 9, 11, 16 and 23 had strong potential against pathogens in vitro. Cytotoxicity results showed compound 9 to be least toxic, it is non-toxic to A549 and U87 cells in MTT assay and exhibits marginal toxicity (15–20%) to human erythrocytes at a concentration of 1000 μg/ml as compared to 100% lysis of cells by 31.25 μg/ml of the standard drug amphotericin B. This compound has MIC values in the range of 1.95–31.25 μg/disc in DDA against different pathogens and may considered to be an important lead antimicrobial molecule for further exploration.

  一系列新型铵类衍生物被合成并检测其抗微生物效果。抗微生物谱的比较显示，化合物9、11、16和23在体外对病原体具有强大的潜力。细胞毒性结果表明，化合物9是毒性最低的，在MTT实验中对A549和U87细胞无毒，并且在1000 μg/ml浓度下对人类红细胞表现出边缘毒性（15%–20%），而与之相比，标准药物两性霉素B在31.25 μg/ml时会导致100%细胞溶解。该化合物在不同病原体的DDA中显示出1.95–31.25 μg/盘的最小抑菌浓度（MIC），可被视为进一步探索的重要抗微生物先导分子。