2,6-di-p-methoxyphenyl-3,5-dimethyltetrahydropyran-4-one | 67405-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-di-p-methoxyphenyl-3,5-dimethyltetrahydropyran-4-one
• 英文别名: r-2,cis-6(e)-bis(4-methoxyphenyl)-trans-3(e),5(e)-dimethyltetrahydro-4H-pyran-4-one；2,6-Di-(p-anisyl)-3,5-dimethyl-tetrahydropyran-4-on；2,6-bis-(4-methoxy-phenyl)-3,5-dimethyl-tetrahydro-pyran-4-one；2,6-Bis(4-methoxyphenyl)-3,5-dimethyloxan-4-one
• CAS: 67405-32-7
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: BLJOIWXYYBHRIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: methanol (67-56-1))
• 沸点：
  489.9±45.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2,6-di-p-methoxyphenyl-3,5-dimethyltetrahydropyran-4-one 生成 2,6-Di-p-anisyl-3,5-dimethyltetrahydropyran-4-ol
  参考文献：
  名称：

  BALIAH V.; MANGALAM G., INDIAN J. CHEM., 1978, B 16, NO 3, 213-215

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 3-戊酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 2,6-di-p-methoxyphenyl-3,5-dimethyltetrahydropyran-4-one
  参考文献：
  名称：

  新型吡喃-4-酮含腙、三唑和异恶唑基团的合成、抗分枝杆菌筛选、分子对接、ADMET 预测和药理学评价：SARS CoV-2 的潜在抑制剂

  摘要：

  呼吸道感染结核病是由结核分枝杆菌引起的，其持续蔓延导致全世界数百万人死亡。因此，需要探索潜在且毒性较小的抗结核药物。在目前的工作中，我们报告了四种不同（腙 7-12、O-乙炔基肟 19-24、三唑 25-30 和异恶唑 31-36）杂化物的合成和抗结核活性。在这些杂种中，9、10、33 和 34 在 3.12 g/mL 时表现出高抗结核活性，抑制率 >90%。杂交体还显示出介于 -6.8 和 -7.8 kcal/mol 之间的良好对接能量。此外，分析了大多数活性分子对结核分枝杆菌和大肠杆菌的 DNA 促旋酶还原能力DNA 旋转酶通过 DNA 超螺旋和 ATPase 旋转酶测定方法。所有四种杂化物都显示出与参考药物相当的良好 IC50 值。此外，通过分子对接，该靶点还被预测为木瓜蛋白酶样蛋白酶（SARS CoV-2 PLpro）的潜在结合物，并观察到良好的相互作用结果。此外，预测了所有目标的吸收、分布、代谢和排泄-毒性

  DOI：

  10.1016/j.molstruc.2023.135461

文献信息

• Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles
  作者：Paramasivam Parthiban、Gopalakrishnan Aridoss、Paramasivam Rathika、Venkatachalam Ramkumar、Senthamaraikannan Kabilan

  DOI：10.1016/j.bmcl.2009.04.038

  日期：2009.6

  Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis, stereochemistry, antimicrobial evaluation and QSAR studies of 2,6-diaryltetrahydropyran-4-one thiosemicarbazones
  作者：S. Umamatheswari、B. Balaji、M. Ramanathan、S. Kabilan

  DOI：10.1016/j.ejmech.2011.01.029

  日期：2011.4

  A series of 2,6-diaryltetrahydropyran-4-one thiosemicarbazones (11-27) were synthesized and characterized for evaluation of potential antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Bacillus subtilis and Klebsiella pneumonia and antifungal activity against Cryptococcus neoformans, Candida albicans, Rhizopus sp., Aspergillus niger and Aspergillus kiwis were evaluated. Compounds 21 and 22 showed maximum inhibition potency at low concentration (6.25 mu g/ml) against P. aeruginosa. For antifungal activity, 20 and 21 were effective against C. neoformans and 22-24 against C. albicans at minimum concentration. Further, the results of QSAR studies of these synthesized compounds indicated the importance of weakly polar component of surface area, hydrophobicity and ionization potential parameters in defining their antimicrobial activity. (c) 2011 Elsevier Masson SAS. All rights reserved.
• Baliah, V.; Mangalam, G., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1986, vol. 25, # 10, p. 947 - 948
  作者：Baliah, V.、Mangalam, G.

  DOI：——

  日期：——
• BALIAH V.; MANGALAM G., INDIAN J. CHEM., 1978, B 16, NO 3, 213-215
  作者：BALIAH V.、 MANGALAM G.

  DOI：——

  日期：——
• Synthesis, antimycobacterial screening, molecular docking, ADMET prediction and pharmacological evaluation on novel pyran-4-one bearing hydrazone, triazole and isoxazole moieties: Potential inhibitors of SARS CoV-2
  作者：N. Ravisankar、N. Sarathi、T. Maruthavanan、Subramaniyan Ramasundaram、M. Ramesh、C. Sankar、S. Umamatheswari、G. Kanthimathi、Tae Hwan Oh

  DOI：10.1016/j.molstruc.2023.135461

  日期：2023.8

  tuberculosis and its unrelenting spread caused millions of deaths around the world. Hence, it is needed to explore potential and less toxic anti-tubercular drugs. In the present work, we report the synthesis and antitubercular activity of four different (hydrazones 7–12, O-ethynyl oximes 19–24, triazoles 25–30, and isoxazoles 31–36) hybrids. Among these hybrids 9, 10, 33, and 34, displayed high antitubercular

  呼吸道感染结核病是由结核分枝杆菌引起的，其持续蔓延导致全世界数百万人死亡。因此，需要探索潜在且毒性较小的抗结核药物。在目前的工作中，我们报告了四种不同（腙 7-12、O-乙炔基肟 19-24、三唑 25-30 和异恶唑 31-36）杂化物的合成和抗结核活性。在这些杂种中，9、10、33 和 34 在 3.12 g/mL 时表现出高抗结核活性，抑制率 >90%。杂交体还显示出介于 -6.8 和 -7.8 kcal/mol 之间的良好对接能量。此外，分析了大多数活性分子对结核分枝杆菌和大肠杆菌的 DNA 促旋酶还原能力DNA 旋转酶通过 DNA 超螺旋和 ATPase 旋转酶测定方法。所有四种杂化物都显示出与参考药物相当的良好 IC50 值。此外，通过分子对接，该靶点还被预测为木瓜蛋白酶样蛋白酶（SARS CoV-2 PLpro）的潜在结合物，并观察到良好的相互作用结果。此外，预测了所有目标的吸收、分布、代谢和排泄-毒性