O4-methyl O1-(2,2,4-trimethylchromen-7-yl) benzene-1,4-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O4-methyl O1-(2,2,4-trimethylchromen-7-yl) benzene-1,4-dicarboxylate
• 英文别名: 1-O-methyl 4-O-(2,2,4-trimethylchromen-7-yl) benzene-1,4-dicarboxylate
• 化学式: C₂₁H₂₀O₅
• 分子量: 352.387
• InChiKey: MJCVHGXCUYYEPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-hydroxy-2,2,4-trimethyl-(2H)-1-benzopyran 、 4-氯甲酰基苯甲酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以36%的产率得到O4-methyl O1-(2,2,4-trimethylchromen-7-yl) benzene-1,4-dicarboxylate
  参考文献：
  名称：

  Novel Heteroarotinoids as Potential Antagonists of Mycobacterium bovis BCG

  摘要：

  A series of 15 heteroarotinoids has been prepared and evaluated for activity against Mycobacterium bovis BCG with the thiourea-containing isoxyl (7) (0.5 mug/mL) as the standard. 2,2,4-Trimethyl-2H-chromen-7-yl 4-(methoxycarbonyl)benzoate (8) displayed the most significant activity (2.0-4.0 mug/mL) in terms of the lowest concentration (mug/mL) (MIC, minimum inhibitory concentration) required to produce a 99% reduction in the number of colonies on a plate as compared to that system free of the agent at the same dilution of the culture suspension. Ethyl 4-{[N-(2,2,4,4-tetramethylchroman-6-yl)thiocarbamoyl] amino}benzoate (9) and {[(1E,3Z,5E)-1-aza-4-methyl-6-(1,2,2,4-tetramethyl(1,2-dihydroquinolyl))hexa-1,3,5-trienyl]-amino}aminomethane-1-thione (10) exhibited activity at 5.0-10.0 and 10.0-20.0 mug/mL, respectively, while the other examples had MIC values of 20 mug/mL or greater. The inhibitory ability of 8 may occur via the inhibition of mycolic acid synthesis in a like manner as found with 7, but this requires further study. The heteroarotinoids are the first examples to exhibit inhibitory ability against the growth of Mycobacterium bovis BCB.

  DOI：

  10.1021/jm0303453

文献信息

• Novel Heteroarotinoids as Potential Antagonists of <i>Mycobacterium</i> <i>b</i><i>ovis</i> BCG
  作者：Chad W. Brown、Shengquan Liu、Jozef Klucik、K. Darrell Berlin、Patrick J. Brennan、Devinder Kaur、Doris M. Benbrook

  DOI：10.1021/jm0303453

  日期：2004.2.1

  A series of 15 heteroarotinoids has been prepared and evaluated for activity against Mycobacterium bovis BCG with the thiourea-containing isoxyl (7) (0.5 mug/mL) as the standard. 2,2,4-Trimethyl-2H-chromen-7-yl 4-(methoxycarbonyl)benzoate (8) displayed the most significant activity (2.0-4.0 mug/mL) in terms of the lowest concentration (mug/mL) (MIC, minimum inhibitory concentration) required to produce a 99% reduction in the number of colonies on a plate as compared to that system free of the agent at the same dilution of the culture suspension. Ethyl 4-[N-(2,2,4,4-tetramethylchroman-6-yl)thiocarbamoyl] amino}benzoate (9) and [(1E,3Z,5E)-1-aza-4-methyl-6-(1,2,2,4-tetramethyl(1,2-dihydroquinolyl))hexa-1,3,5-trienyl]-amino}aminomethane-1-thione (10) exhibited activity at 5.0-10.0 and 10.0-20.0 mug/mL, respectively, while the other examples had MIC values of 20 mug/mL or greater. The inhibitory ability of 8 may occur via the inhibition of mycolic acid synthesis in a like manner as found with 7, but this requires further study. The heteroarotinoids are the first examples to exhibit inhibitory ability against the growth of Mycobacterium bovis BCB.