1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)ethanone | 31367-55-2

• 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: 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)ethanone
• 英文别名: 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-ethanone；1-(5,7-Dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-aethanon；1-(5,7-dimethoxy-2,2-dimethylchromen-8-yl)ethanone
• CAS: 31367-55-2
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: JELWYGQTQBQPGH-UHFFFAOYSA-N

物化性质

• 熔点：
  105.5-106 °C
• 沸点：
  404.4±45.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)ethanone 在 Oxone 、 溴化铵 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到1-(4-bromo-3-hydroxy-5,7-dimethoxy-2,2-dimethyl chroman-8-yl)ethanone
  参考文献：
  名称：

  Drug efficacy of novel 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans; evaluated via DNA gyrase inhibition, bacterial cell wall lesion and antibacterial prospective

  摘要：

  In this study, novel 3-O-methoxy-4-halo, disubstituted-5,7-dimethoxy chromans with bacterial cell wall degrading potentials were synthesized, characterized and evaluated as DNA gyrase inhibitors and antibacterial agents. Compounds were showed a broad spectrum of antimicrobial activity against both Gram(+ve) bacteria (S. aureus (MTCC 3160), C. diphtheriae (MTCC 116), S. pyogenes (MTCC 442)) and Gram(-ve) bacteria (E. coli (MTCC 443), P. aeruginosa (MTCC 424), K. pneumoniae (MTCC 530)). Further, a molecular docking study was carried out to get more insight into the binding mode of present study compounds to target proteins (PDB ID: 2XCT (S. aureus DNA gyrase A), PDB ID: 3G75 (S. aureus DNA gyrase B), PDB ID: 3L7L (Teichoic acid polymerase). In the results, 14 > 20 > 24 > 12 > 18 > 17 were found as the most active against almost all executed activities in this study. The predicted Lipinski's filter scores, SAR, pharmacokinetic/pharmacodynamics, and ADMET properties of these compounds envisioned the druggability prospects and the necessity of further animal model evaluations of 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans to establish them as an effective and future antibiotics.

  DOI：

  10.1016/j.bmc.2018.05.016
• 作为产物：
  描述：

  8-acetyl-5,7-dimethoxy-2,2-dimethyl chroman-4-one 在 sodium tetrahydroborate 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)ethanone
  参考文献：
  名称：

  Drug efficacy of novel 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans; evaluated via DNA gyrase inhibition, bacterial cell wall lesion and antibacterial prospective

  摘要：

  In this study, novel 3-O-methoxy-4-halo, disubstituted-5,7-dimethoxy chromans with bacterial cell wall degrading potentials were synthesized, characterized and evaluated as DNA gyrase inhibitors and antibacterial agents. Compounds were showed a broad spectrum of antimicrobial activity against both Gram(+ve) bacteria (S. aureus (MTCC 3160), C. diphtheriae (MTCC 116), S. pyogenes (MTCC 442)) and Gram(-ve) bacteria (E. coli (MTCC 443), P. aeruginosa (MTCC 424), K. pneumoniae (MTCC 530)). Further, a molecular docking study was carried out to get more insight into the binding mode of present study compounds to target proteins (PDB ID: 2XCT (S. aureus DNA gyrase A), PDB ID: 3G75 (S. aureus DNA gyrase B), PDB ID: 3L7L (Teichoic acid polymerase). In the results, 14 > 20 > 24 > 12 > 18 > 17 were found as the most active against almost all executed activities in this study. The predicted Lipinski's filter scores, SAR, pharmacokinetic/pharmacodynamics, and ADMET properties of these compounds envisioned the druggability prospects and the necessity of further animal model evaluations of 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans to establish them as an effective and future antibiotics.

  DOI：

  10.1016/j.bmc.2018.05.016

文献信息

• Sutherland, University of Queensland Papers, Department of Chemistry, 1949, vol. 1, # 35, p. 1,9
  作者：Sutherland

  DOI：——

  日期：——
• Bacteriostatic heterocycles from Euodia lunu-ankenda
  作者：Mangala D. Manandhar、Falak A. Hussaini、Randhir S. Kapil、Aboo Shoeb

  DOI：10.1016/s0031-9422(00)80844-4

  日期：1985.1
• Tsukayama, Masao; Sakamoto, Tsukasa; Horie, Tokunaru, Heterocycles, 1981, vol. 16, # 6, p. 955 - 958
  作者：Tsukayama, Masao、Sakamoto, Tsukasa、Horie, Tokunaru、Masamura, Mitsuo、Nakayama, Mitsuru

  DOI：——

  日期：——
• ANSARI M. A.; MATHUR K. B. L.; AHLUWALIA V. K., INDIAN J. CHEM., 1978, B 16, NO 8 702-703
  作者：ANSARI M. A.、 MATHUR K. B. L.、 AHLUWALIA V. K.

  DOI：——

  日期：——
• Drug efficacy of novel 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans; evaluated via DNA gyrase inhibition, bacterial cell wall lesion and antibacterial prospective
  作者：Thangarasu Ponnusamy、Manikandan Alagumuthu、S. Thamaraiselvi

  DOI：10.1016/j.bmc.2018.05.016

  日期：2018.7

  In this study, novel 3-O-methoxy-4-halo, disubstituted-5,7-dimethoxy chromans with bacterial cell wall degrading potentials were synthesized, characterized and evaluated as DNA gyrase inhibitors and antibacterial agents. Compounds were showed a broad spectrum of antimicrobial activity against both Gram(+ve) bacteria (S. aureus (MTCC 3160), C. diphtheriae (MTCC 116), S. pyogenes (MTCC 442)) and Gram(-ve) bacteria (E. coli (MTCC 443), P. aeruginosa (MTCC 424), K. pneumoniae (MTCC 530)). Further, a molecular docking study was carried out to get more insight into the binding mode of present study compounds to target proteins (PDB ID: 2XCT (S. aureus DNA gyrase A), PDB ID: 3G75 (S. aureus DNA gyrase B), PDB ID: 3L7L (Teichoic acid polymerase). In the results, 14 > 20 > 24 > 12 > 18 > 17 were found as the most active against almost all executed activities in this study. The predicted Lipinski's filter scores, SAR, pharmacokinetic/pharmacodynamics, and ADMET properties of these compounds envisioned the druggability prospects and the necessity of further animal model evaluations of 3-O-methoxy-4-halo disubstituted 5,7-dimethoxy chromans to establish them as an effective and future antibiotics.