(6-methoxy-1,1,4,4-tetramethylisochroman-5-yl)amine | 551939-07-2

• 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: (6-methoxy-1,1,4,4-tetramethylisochroman-5-yl)amine
• 英文别名: 1,1,4,4-Tetramethyl-6-methoxy-5-amino-3,4-dihydro-1H-2-benzopyran；6-methoxy-1,1,4,4-tetramethyl-3H-isochromen-5-amine
• CAS: 551939-07-2
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: MXBPPGYJKGHEDC-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  350.6±42.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对硝基苯甲酰异硫氰酸盐 、 (6-methoxy-1,1,4,4-tetramethylisochroman-5-yl)amine 以 四氢呋喃 为溶剂， 反应 24.0h， 以81%的产率得到N-[(6-methoxy-1,1,4,4-tetramethyl-isochroman-5-yl)carbamothioyl]-4-nitro-benzamide
  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
• 作为产物：
  描述：

  1,1,4,4-tetramethyl-6-methoxy-3,4-dihydro-1H-2-benzopyran 在 盐酸 、 titanium(III) chloride 、 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 14.0h， 生成 (6-methoxy-1,1,4,4-tetramethylisochroman-5-yl)amine
  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

• Heteroarotinoids containing urea or thiourea linker
  申请人：The Board of Regents for Oklahoma State University

  公开号：US06586460B1

  公开（公告）日：2003-07-01

  Compounds, known as heteroarotinoids, having varying abilities to inhibit growth of certain cancerous cells, induce normal cell differentiation, and induce apoptosis or death of cancerous cells, of the general formula: in which: Ar and Ar′ denote aryl substituents, and wherein at least one of said aryl substituents comprises an aromatic ring having at least one heteroatom in a fused, partially saturated ring; W denotes O or S; and Q denotes H or i-C3H7.

  化合物，被称为杂环芳烃，具有不同的抑制某些癌细胞生长的能力，诱导正常细胞分化，并诱导癌细胞凋亡或死亡，其通式为：其中：Ar和Ar'表示芳基取代基，其中至少一个芳基取代基包括一个具有至少一个杂原子的融合、部分饱和的环的芳香环; W表示O或S; Q表示H或i-C3H7。
• US6586460B1
  申请人：——

  公开号：US6586460B1

  公开（公告）日：2003-07-01
• 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.